People have long been fascinated by their fellow humans’ daily routines — particularly the routines of the famous and successful.

We feel there are likely habits common to high-achievers, which, if duplicated, would help us all elevate our own work. This is especially true of the choice of when to wake up each day. There seems to be special weight placed on this decision, a feeling perhaps born of the idea that how you start something determines how the rest of it will go. The time you get up each day seems to be a potentially impactful pivot point from which the quantity and quality of one’s ensuing work and decision-making will flow.

It’s popularly thought that the best time to wake up is early in the morning. “The early bird gets the worm”; “Early to bed, and early to rise, makes a man healthy, wealthy, and wise.” Beyond even the idea that rising early has a practical benefit in aiding productivity, there’s a moral connotation to this habit as well; early risers are perceived as having more discipline, while their late-rising peers are often perceived as lazy.

Is there truly a correlation between waking up early and success?

The Morning Person as Success Story: Considering the Evidence

I decided to find out by re-reading Mason Currey’s Daily Rituals: How Great Minds Make Time, Find Inspiration, and Get to Work. The book is a collection of short descriptions of the daily routines of 161 eminent authors, mathematicians, architects, and artists — folks who did creative work and were able to set their own schedules. As I read each entry, I kept a tally of when each individual woke up. I only marked down those for whom a specific time was given, skipping entries where the time was kept more vague (e.g., “early morning” or “early afternoon”). In the few cases where a person woke up not at a straight o’clock (i.e., _:00) and instead arose at _:30, or were said to arise sometime between __ and __, I “rounded” to the earlier hour in half the cases, and to the later hour in the other half. My aim was just to get a feel for the general range of times that these folks got up each day.

This gave me the wake-up times for a sample set of 68 individuals, and these have been graphed below:

It’s worth noting that almost all those who woke up at 4 am took a long nap either several hours after rising or in the afternoon.

As you can see, there were indeed many early risers among this high-performing group, with the most common wake-up time being 6 a.m. Yet it is just as significant to observe that there were as many folks who woke up at 8 a.m. as 5 a.m., and almost as many who woke up from 7 a.m. on, as at 6 o’clock or earlier. And those in the former category were no less creative/productive/successful than the latter. Having a good morning to set the tone of your day, it seems, can happen at almost any time.

The real takeaway, then, is that there isn’t in fact one “right” time to wake up if you want to be creative and successful. The answer to the question of “What time should you wake up to do your best work?” is: “Whatever time works best for you.”

The novelist Bernard Malamud came to this same conclusion:

There’s no one way—there’s too much drivel about this subject [of copying other people’s routines]. You’re who you are, not Fitzgerald or Thomas Wolfe. You write by sitting down and writing. There’s no particular time or place—you suit yourself, your nature. How one works, assuming he’s disciplined, doesn’t matter. If he or she is not disciplined, no sympathetic magic trick will help. . . . Eventually everyone learns his or her own best way. The real mystery to crack is you.

Experiment. Be self-reliant. Find your own optimal routine. It’s worth noting that not everyone Mason profiled began working right after waking up; they might arise in the morning but first attend to other important tasks and activities before beginning work in the afternoon or evening. They might get in a morning workout or spend the first few hours of the day with loved ones. There are multiple components in one’s schedule to play with.

Now, all this being said, there was one commonality between all the profiles that was so nearly universal that it should be given real credence: despite the many varied ways in which each individual arranged their daily routine, almost all of them had a routine, and stuck to it religiously.

The Importance of a Regular, Consistent Daily Routine

“My experience has been that most really serious creative people I know have very, very routine and not particularly glamorous work habits,” explained the modern composer John Adams.

“Routine is a condition of survival,” asserted the writer Flannery O’Connor.

The novelist John Updike felt that having a daily routine was so important because it “saves you from giving up.”

These sentiments were shared even among those whose overall personalities and lifestyles were fairly hedonistic; for example, though the modern artist Francis Bacon and the writer Ernest Hemingway could be called night owls and sometimes stayed up late partying (the former drank six bottles of wine a day), they would nonetheless still wake up early and get to work, hangovers and getting enough hours of sleep be damned. A productive morning and day were always on the docket. As Papa put it, “You have to work every day. No matter what has happened the day or night before, get up and bite the nail.”

Further, among the individuals Currey profiled, such revelry was far more the exception than the rule. Despite the reputation of creative types as living freewheeling, iconoclastic lives, the vast majority kept to routines — both within and outside their work schedules — that were surprisingly quiet, prosaic, and closed-in. “I love the cell,” Voltaire exclaimed, and so did many of his productive peers throughout time.

The morning habits and daily rituals of famous authors and artists typically look something like this: wake up, drink a glass of water, eat breakfast, do a few hours of work, eat lunch, do a few more hours of work, eat dinner with spouse, take a walk (if one stand-out commonality did emerge from surveying all these routines, it’s taking a daily walk, or two; almost a third of the individuals profiled kept this habit), watch television or read a book, go to bed. Entire days would pass like this. They went out surprisingly seldom, and this was not an incidental choice but an intentional one; limiting distractions expanded their creativity.

Or as Gustave Flaubert put it, “Be regular and orderly in your life like a bourgeois so that you may be violent and original in your work.”

With our archives 4,000 articles deep, we’ve decided to republish a classic piece each Sunday to help our newer readers discover some of the best, evergreen gems from the past. This article was originally published in March 2021.

This article was originally published on The Art of Manliness.

When you have a high-responsibility job, your work hours can readily bleed beyond the 9-to-5. You’ve got a lot of tasks that seem urgent and important and an endless number of people who need responding to. This is of course especially true in the age of smartphones and digital communication, when bosses and colleagues feel free to message you at any time — even when you’re nominally “off the clock.”

The problem of ever-expanding work hours may be more prevalent these days, but it’s not new.

General George Marshall faced the issue almost a century ago. And found a way to overcome it.

As Chief of Staff of the United States Army during World War II, Marshall oversaw the expansion of a military ranked seventeenth in the world into the most powerful fighting force in human history. He managed nine theaters of war, helped oversee the Manhattan Project, and directed millions of personnel across the globe. His job was arguably the most complex administrative role of the twentieth century.

Day and night, there was always some issue, in some branch, in some part of the world that Marshall could be tending to, and that he could have convinced himself was urgent — the fate of democracy hung in the balance, after all!

But Marshall walked out of the War Department at 5:00 PM almost every single day and didn’t think about work until he showed up to the office the next morning.

How did a guy who oversaw the largest, most complex military campaign in human history do that?

The Marshall Plan — For Taming His Work Schedule

Here’s how General George Marshall kept the tentacles of his work responsibilities from expanding into an all-encompassing chokehold:

Marshall Gutted the Bureaucracy

When Marshall took over as Chief of Staff in 1939, the War Department was a mess. Over sixty different bureaus and agencies had direct access to his office, which meant he spent most of his time refereeing petty jurisdictional squabbles instead of planning a war. Marshall described himself as being “worked to tatters on minor details.”

So in early 1942, he blew the whole thing up. He directed Brigadier General Joseph McNarney to streamline the organization. The results were dramatic. The number of people with direct access to Marshall dropped from over sixty to roughly six. He created semi-autonomous commands — Army Ground Forces, Army Air Forces, Services of Supply — that handled their own training and supplies procurement.

And he established the Operations Division (OPD), which functioned as a single command post that filtered the entire war’s worth of data into a manageable stream of intelligence and proposed actions.

The OPD was the key to the whole thing. Theater commanders had to send copies of all combat-related messages to the OPD, and the OPD’s job was to synthesize that information and only bring the “broad phases of plans or changes” to Marshall. When Marshall sat down at his desk each morning, the information had already been distilled by competent people. His only job was to exercise judgment.

Marshall Demanded the One-Page Memo

Marshall had a rule: if you couldn’t explain your problem and propose a solution on a single page, you didn’t understand the problem yet. The one-page memo requirement forced his staff to do the hard thinking before they walked into his office, which meant Marshall could review dozens of critical strategic questions in the time it took other commanders to get through a single briefing.

Marshall Maintained Strict Boundaries

Marshall’s daily routine was boringly rigid, which is what made it effective.

He woke up at 6:30 AM and was at the War Department by 7:30. He’d get a global briefing at 8:00, and then he’d dive straight into strategic work through the morning.

He ate lunch and followed that up with a power nap. Marshall was a big advocate of the midday nap and pushed Eisenhower and MacArthur to adopt the habit.

After his nap, he worked through the afternoon until 5:00 PM.

At 5 PM on the dot, he’d leave the office for the day.

What did he do in his personal time?

Horseback riding. It was a non-negotiable part of his day. Marshall rode with his stepdaughter, Molly, or alone with his dog, Fleet. He specifically refused to ride with colleagues because he didn’t want “office talk” creeping into his recovery time.

After riding, he had dinner with his wife, Katherine, and was in bed by 9:00 PM.

Marshall understood that if you work yourself to exhaustion, you won’t have the mental clarity and energy to actually do the work you’re supposed to do. He was able to get more done during the time he did work because he was well-rested (thanks to the power nap and strict sleeping schedule) and refreshed (thanks to horseback riding and strict leave-the-work-at-work policy). And by standardizing his schedule, he eliminated that low-grade decision fatigue that makes you stare at your inbox for 10 minutes without actually writing any emails or causes you to snap at your kid for asking a simple question.

Even on the morning of December 7, 1941, Marshall was out on his horse, Prepare, at Fort Myer. Some people at the time criticized the optics. Why wasn’t the Army Chief of Staff at the office as soon as that Day of Infamy occurred? But Marshall understood there was nothing he could do immediately, so he took the time to get his mind right before he had to get down to business. His ability to remain “especially cheerful and optimistic” in the hours and days after Pearl Harbor was a direct product of those physical and emotional reserves he built up through deliberate rest and relaxation.

So, What Can We Steal From Marshall?

While we may not have to manage nine theaters of war, nor have Marshall’s latitude in restructuring administrative operations, I think we can use some of Marshall’s principles to tame our own workload into a more humane schedule. It’s all about working effectively when you’re “on the clock,” and actually checking out when you’re off it.

Cut the number of communications you have coming in. How many people have direct access to your time and attention? How many pings and dings do you receive?

Marshall cut his direct reports from sixty to six. You may not be able to be that aggressive, but you can identify the nonsense that eats your day without producing anything useful. Aggressively reduce the number of apps you have to check for communication. Use filters in your email so that only the important stuff shows up there. Turn off notifications from web services that you use. Use your phone’s Do Not Disturb feature and only allow VIPs to call or text you. Don’t attend meetings where you’re not needed. Get rid of the deadwood.

Organize your communications and answer them in blocks. You don’t have an OPD to synthesize your info and give you a one-page memo about it. But you can turn the intelligence you receive into a manageable stream and claw back a lot of time and bandwidth by keeping information and conversations organized into set channels.

In my conversation with business efficiency expert Nick Sonnenberg, he said that 20% of an employee’s time can be spent just looking for where information about a certain topic/project ended up. To shrink these “scavenger hunts,” he recommends designating certain channels for certain communications: text for personal matters, email for external communications with clients, vendors, and partners, and apps like Slack for internal team messages. By eliminating the search for where particular information resides, Nick’s found that workers gain back hours of time.

I also recommend establishing a “correspondence hour” — set blocks of time when you answer messages. In the morning, I glance through my emails, texts, and messaging apps and take action on anything that needs action. At night, I do the same thing. Doing this in set, consolidated blocks saves time over constantly ping-ponging back and forth through apps throughout the day.

Pick your 5:00 PM. You don’t need to literally knock off every day at 5:00 PM like Marshall did, but you need to establish a hard boundary where you take off your general’s cap and put on your personal one.

Marshall rode every evening because, without those hours on the horse, he knew he’d eventually start making bad calls with millions of lives on the line. Find your horseback riding. It could be working out, building model trains, or reading a book. Whatever. Pick something that has nothing to do with your job and do it as a way to transition from work mode to private mode.

If you’re an employee rather than a boss, it may be harder to say no to responding to messages when you should be off the clock. But try to have that boundary-setting conversation with your supervisor. And set expectations with your own behavior. If you always respond to messages in the evening and on the weekend, people will take that as the norm; if you don’t, then they won’t expect you to.

Nick also recommended keeping in mind that the more emails you send out, the more you’ll get back. So avoid the temptation to send “just one” response on a Saturday, lest you find yourself caught up in a back-and-forth that runs all weekend long. If you need to get a response off your mind, write it up, and then schedule it to be sent first thing Monday morning.

General George Marshall went on to create the Marshall Plan, rebuild Europe, and win the Nobel Peace Prize. He did all of it on eight-hour days with absolute focus, discipline, and a genuine understanding of human limits. He understood that a man’s effectiveness has a lot more to do with the quality of the work he does at his desk than with how many hours he sits there.

This article was originally published on The Art of Manliness.

I’m in my late thirties and have been laid off twice in my working years. This is not an unusual experience, especially in the post-COVID era, which some have termed a time of “forever layoffs.” Nearly half of all working adults have been laid off at some point in their career and most working employees are worried about layoffs on a regular basis.

The first time it happened to me was in 2012 when the small marketing agency that I’d been with for only a year went belly up. I was young, didn’t have many responsibilities in life just yet, and the job hunt went quite well; I secured a new gig within a handful of weeks. The second time I was laid off was in 2024, as part of a larger set of cuts at a billion-dollar tech company I had been with for about three years. Twelve years after my first layoff, not only was the economy wildly different, but I had a family, three young kids, and a mortgage to worry about. It took almost a year of ups, downs, and freelance projects to get back into comfortable employment. Those two instances ended up being pretty different experiences, and yet a similar set of tactics helped me get through both times.  

There will inevitably be a flood of anxiety after you’ve been laid off. But once your heart rate has calmed down and you’re able to move beyond panic mode, do these five things to get yourself in a good position to survive and move forward.  

Nail Down Your Financial and Insurance Logistics  

As hard as it can be in those first days after being let go, you need to start thinking right away about your finances and health insurance. It can be hard to do so without catastrophizing, but it’s important to think clearly and strategically about how you and your family will weather the financial unpredictability of the coming weeks and months.

Insurance

First, consider your insurance situation. Be sure that you have information from HR about when your benefits lapse — it can be immediate, but sometimes it’s a few weeks or even months down the road.

If you’re carrying the household’s insurance and have the option to move to a spouse’s insurance plan, definitely go that route, even if it’s not for the long-term. Having coverage is better than not having coverage.

If that’s not an option, COBRA is a federal government program that allows you to receive the same exact insurance you had with your former employer, for a period of 18-36 months after being let go. The major difference is that you’ll have to pay the entire cost of the premiums. If you’re in a field with good benefits, it may be exorbitantly expensive to pay out of pocket. In that case, your state’s insurance marketplace is where to look next. It can be confusing if you’ve never dealt with it before; your former employer’s HR department may be able to help you find a broker to help with that process. Don’t hesitate to ask them these types of questions.  

Finances

You also have to think realistically about your budget. How much do you have in your bank account? How much severance are you receiving, if any? How much do you have in emergency savings or other accessible accounts (that is, stocks or other investments that don’t have withdrawal penalties, rather than retirement accounts)? Make sure you know exactly how long you can make it without your income.

Next, apply for government unemployment benefits. Each state has their own online portal (and set of rules). You’ll be entitled to a percentage of your previous wages (typically 50%) for an entire year. It’s a hassle, and there are a lot of forms, including weekly online check-ins about your job search, but there’s no reason to not take advantage of unemployment checks. After all, your taxes have been paying into that fund for as long as you’ve been working!

Reach Out and Start Networking

Time to share some harsh truth: In today’s job market, it’s nearly impossible to just apply for a job that you found online and get invited to a screening interview, let alone make it all the way through the lengthy multi-interview + work test process that pervades modern job hunting. In the vast majority of cases, networking will get you farther than scrolling job listings online. It bears repeating: while networking does not necessarily have the same immediate ROI as applying for random jobs, it will net you greater returns in the long run.

In particular, it’s worth reaching out to your weak ties — those loose connections you made in college or through work or church. You aren’t quite friends with these folks, but know them well enough that reaching out in this scenario isn’t weird. Go creeping on LinkedIn to see where folks work; if a company seems interesting, there’s no harm in sending a message like:

“Hi there! I know it’s been a while since we’ve talked. I hope you’re doing well — I loved seeing that family picture on Facebook. I wanted to reach out and say hello because I was recently let go from my job of five years. I’m trying to get a feel for what the market is like and what’s out there and would really appreciate a 30-minute chat if you’re willing. If the timing isn’t right, no worries, but it’d be great to catch up a bit.”

If they agree to chat, don’t make it just about finding a job at their company; it really should be a broader focus on if they know of anyone or anything helpful. If you talk and something seems like a good fit, they’ll let you know. (After you talk, make sure to send a thank you note or message!)

Beyond those weak ties, also do some fresh networking both online and in your community. With a quick internet search, you’ll be able to find digital and IRL networks of folks in your industry. Again, the ROI is not always apparent, but genuine networking — with the goal of just getting to know people and getting your name and face out there — always has a way of paying off in the long run.  

P.S. This is a great reason to never burn bridges on your way out of any job.

Set Some “Working” Hours

In my observations, it seems that there are two types of responses to being out of work: either you can’t seem to get off the couch to do anything or you turn that anxiety into a kind of hyperactivity, spending every waking moment on the phone or computer. Both of those approaches have problems that can be remedied by doing your best to set daily “working” hours.

Don’t try to replicate a full work week; set aside 3-4 hours per day for networking, job hunting, building up your skills, and the like. The work of finding work is mentally taxing (and, let’s be honest, often defeating) in a way that a “real” job is not. There’s no psychological security at all; in fact, you’re mostly dealing with feelings of existential dread the whole time. As such, your willpower gets depleted rather quickly. After half a day or so, you’ll experience diminishing returns and it won’t be worth the additional mental energy to keep going. You can only scroll through so many job listings and write so many cover letters in a day before you start to feel your soul escaping your body.

Conduct Career Experiments

My initial response to being let go was, naturally enough, to apply for positions similar to what I just held. That makes total sense and should absolutely be your first plan of attack. Unless you have a sizeable financial cushion, it’s not a bad idea to do this even if you plan on changing careers — it may make for a nice fallback should that other route not work out as quickly as you hoped.

Within a few weeks, though, it was easy to blast through applying for the roles that most matched my resume. After that, I took the liberty of getting a little more creative and looking for roles that I wasn’t perfectly qualified for but suited my interests a bit more. Even though my career has been in online media and marketing, when I was laid off in 2024 I branched out and had a couple interviews outside my comfort zone, including with a small coffee roaster and a large airplane manufacturer. I even considered going back to school. I didn’t end up doing any of those things, but I thought long and hard about them and did learn a lot about what it would be like to jump industries, to start at the bottom of a workplace food chain, and the practicalities of starting fresh.

If you’ve ever thought of doing something different with your career, perhaps being let go is the spark you need to jumpstart that process. Don’t be afraid to look outside of what you know, especially if it’s an industry that’s been hit hard with layoffs (perhaps making it all that much harder to get a new job in that field).  

Do Your Best to Relax

One of the things that bothered me most — and which happened both of the times I was laid off — was hearing from folks about how I now had some time to sleep in, relax a bit, and enjoy “funemployment.” As if! There was no way I could sleep in or really even remotely enjoy myself while in the midst of desperately trying to find a way to replace that income as soon as possible. It’s very hard to relax when you’ve been laid off versus when you’ve left a job on your own terms, even if you’ve been lucky enough to receive severance pay.

That said, each time it’s happened to me, I forced myself to at least do some activities that would normally bring me joy — even if they didn’t immediately do so in the moment. For me, it was hiking/walking every day, reading, and doing some extra cooking/baking. While there’s a time and place for some true vegging out with Netflix, it’s best to shoot for a more active type of relaxation that comes from using your body and brain in a way that you get deeper fulfillment from. Regular exercise should especially be part of that routine. If you just lounge around on the couch all day, you can quickly fall into a pattern that’s hard to get out of.

It’s likely going to be hard to truly relax and let yourself recharge, but at least go through the motions. Some of it will stick and you’ll at least build up a good routine of caring for your mind and body while without work.

The job market and the process of finding work after a layoff is unpredictable. I simply cannot say that it will all work out in a timely manner. But if you follow these steps, you’ll at least have a better setup for success than you would have otherwise. Best of luck out there!

This article was originally published on The Art of Manliness.

We usually think of money as something very practical, concrete, and secular; we earn it, save it, spend it, and crunch the numbers behind it. But money is never just about money: it reflects our values, our priorities — and even our spiritual life.

My guest today, Tom Levinson, knows this well. He’s a financial advisor who studied religion at Harvard Divinity School and thought about becoming a rabbi. Now, he helps people navigate not just their portfolios, but the deeper questions that come with them.

In today’s conversation, Tom shares the greater meaning around money, what the Jewish, Christian, and Islamic religions say about it, and how financial practices like budgeting can be spiritual disciplines.

Resources Related to the Podcast

• All That’s Holy: A Young Guy, an Old Car, and the Search for God in America by Tom Levinson
• AoM Article: The Spiritual Disciplines — Simplicity
• AoM Podcast #363: Budgeting Doesn’t Have to Suck

Connect With Tom Levinson

This article was originally published on The Art of Manliness.

In the years after World War I, longtime Army colleagues and friends George S. Patton and Dwight D. Eisenhower contemplated what would happen if another global conflict broke out. As Patton envisioned it: “In the next war, I’ll be the Stonewall Jackson, and you can be the Robert E. Lee. Ike, you do the big planning, and you let me go in and shoot up the enemy.”

And that’s pretty much how things worked out in World War II.

Eisenhower led from Allied headquarters as Europe’s Supreme Commander, while Patton served on the ground as commander of the Third and Seventh armies. 

Ike, who lacked battlefield experience, was nonetheless brilliant as a theater commander. Having spent his career as a highly effective staff officer, he had a genius for planning, marshaling material, organizing logistics, and practicing diplomacy. Charming, modest, flexible, and steady, he excelled at getting the disparate and sometimes rivalrous Allied leaders to work together, interfacing with politicians and the press, and keeping all the pieces of a monumental war effort sorted and spinning.

Patton, on the other hand, had little patience for politicking and wasn’t lauded for his ability to formulate high-level plans. But, he possessed all the traits necessary for superior battlefield command. Bold and aggressive, he executed missions with mastery and confidence and advanced with relentless drive.

While each man’s position and responsibilities were different, each excelled in his particular role.

Ike was the consummate strategist. 

Patton was born to be an operator.

Strategists Versus Operators

Andrew Wilson, a professor at the Naval War College, describes the difference between Eisenhower and Patton as the difference between having a bent toward strategy versus having a bent toward operations. 

Wilson defines strategy as “the means by which you translate political purpose” — what the political leadership hopes to achieve with a war — “into military action, and how it is that you anticipate military action to deliver your political purpose. . . . So strategy is the bridge between policy and military actions.”

Operations, he says, are those military actions — “essentially the big muscle movements, the battles.”

Those who excel in that second kind of work — operators — do best on the ground and in the field. They excel at, and derive satisfaction from, practicing and carrying out a certain skill, craft, or art.

Those who excel at the first kind of work — strategists — do best in high-level positions. They excel at, and derive satisfaction from, overseeing, organizing, and supervising those who practice and carry out skills, crafts, and arts.

Another way to describe the strategists versus operators dichotomy is as managers versus tacticians.

It’s a distinction in men’s proclivities that extends beyond the military context, and it’s crucial to know which category you fall into. 

Are You a Strategist or an Operator?

While there are a few men who are adept at both strategy and operations, most primarily lean toward one over the other.

Problems arise when men don’t have the self-awareness and foresight to understand their personal strengths and propensities, and end up in a role for which they are ill-suited.

Strategists Becoming Operators 

Sometimes a man is doing well as a manager type, but may desire a job in the field, perhaps because such work seems “sexier.” For example, he may have done well for years as a supervisor within a company, but thinks about striking out on his own and becoming an entrepreneur, even though the skill set necessary for success in the former pursuit isn’t likely to translate to success in the latter.

Eisenhower thought about making this kind of shift.

In the lead-up to WWII, Ike thought he’d like to work alongside Patton and become the commander of an armored regiment. He had never seen combat; because he was so good at training others, he had been kept stateside during WWI and tasked with preparing troops to deploy. Having missed out on the consummate experience of a military career during the First World War, he was determined to get into the field during the Second.

So when in 1941, a general in the War Plans Division asked Eisenhower to consider joining its staff in Washington, Ike demurred. He really liked the prospect of that position, and knew he’d do well there, but felt that a field command was something he was supposed to prefer. He felt conflicted, and worried he’d “pass[ed] up something I wanted to do, in favor of something I thought I ought to do.” 

Eisenhower needn’t have worried. While he continued to position himself for field command, his administrative abilities were too valuable to be dispensed with, and he was eventually appointed chief of staff to the commander of the Third Army, then Chief of the War Plans Division, and eventually Supreme Allied Commander. Ike’s sense of personal satisfaction, and the fate of world history, benefitted from his sticking to these strategic positions.

Operators Becoming Strategists

What happens more often than managerial men trying to shift into tactical roles is tacticians being promoted into administrative positions. Those who excel in operational roles are frequently moved up the ranks. The problem is, the skills required to succeed as tactical operators don’t typically translate into success as strategic supervisors. This is the essence of the “Peter principle.” And not only may a tactician placed in a managerial or executive job struggle to be competent in that position, he is also unlikely to enjoy it. 

Entrepreneurs who successfully launch start-ups often don’t transition well to becoming the CEOs who run them. Fitness coaches who excel at training clients frequently flounder at owning their own gyms. Pastors who have the skill set to plant churches don’t always have the skill set to oversee the large, established congregations they grow into. Doctors who like practicing hands-on medicine won’t be satisfied spending their days supervising teams of nurses. Academics who enjoy teaching end up less happy as deans than they were as professors. 

Writers and artists, who initially function as fully autonomous operators, sometimes try hiring assistants and social media gurus to expand the empire around their “brand,” but find they’d rather keep their “business” smaller than to give over any of the time they could be creating to managing other people. 

Sometimes an operator has to transition to being a strategist because the fieldwork they do is physical in nature and takes a toll on the body. As a man who works in the trades gets older, for example, he may find it desirable and/or necessary to move from working on projects himself to supervising the work of others. 

But oftentimes, an operator ends up in a managerial position because he feels he’s supposed to take it and defaults to following the standard professional trajectory. The next rung up the ladder may take someone out of the field, but the position comes with more money, power, and/or status. A man thinks he ought to keep moving up in the world, even if that “advancement” puts him into a position he’s less suited for and finds less fulfilling.

Do You Want to Be in the War Room or in the Trenches?

It’s important to know who you are: a strategist or an operator.

If you’re a manager type, lean into that, even if that job may not seem as sexy as others. Administrators are absolutely crucial in keeping the world spinning round, and even help win world wars. 

If you’re the tactician type, do some real reflection before you accept that “promotion.” Is the benefit in money and status worth the tradeoff in fulfillment that comes from doing a job you’re brilliant at and love? It’s okay to recognize that you like carrying out orders more than formulating them. And it’s okay to value the chance to practice the things you’re really skilled at more than a bigger office. 

When Eisenhower was serving as Allied Supreme Commander in North Africa during WWII, his forces experienced some initial setbacks on the battlefield, and the Army’s Chief of Staff, George Marshall, suggested that Ike bring Patton in to serve as his deputy and oversee the fighting. But Patton balked at the idea of taking a more administrative job. He understood that he could do more good on the ground than at HQ, and that an operator belongs in the field — not behind a desk.

With our archives 4,000 articles deep, we’ve decided to republish a classic piece each Sunday to help our newer readers discover some of the best, evergreen gems from the past. This article was originally published in January 2023.

This article was originally published on The Art of Manliness.

A few months ago, we published an article on 11 personal finance goals for your 20s. Today we take a look at 7 personal finance goals for your 30s. While many of the goals you should set during this decade of your life are simply a continuation of those you hopefully started on in the previous one, your thirties bring some unique personal finance challenges that didn’t exist when you were a relatively carefree 20-something. As a friend once put it, “In your 30s, you’re just running.” You’re likely married, have small children, and your career is starting to take off — everything’s launching and/or accelerating at once. And with these new responsibilities come new personal finance goals.

As you read the suggested personal finance goals for your 30s, keep in mind that everyone is in a different place, so naturally everyone is going to have different objectives. But if you’re feeling confused and overwhelmed about money, it’s sometimes helpful to see suggestions for milestones to hit at certain points in your life. You can then take those broad suggestions and refine them so they fit your personal circumstances.

(In your 40s? We also have a guide to finance goals for that decade of life.)

1. Save six months of income in your emergency fund. 

Hopefully by now you’ve started an emergency fund. In your 20s, the goal was to get at least $1,000 in your savings account before you started paying off your debt. This provided a small cushion to prevent your financial life from derailing in the face of unforeseen expenses. In your 30s, you likely have more on the line than you did in your 20s — like a wife and kids to take care of and a mortgage. While having $1,000 in savings will certainly help, you’ll want even more security than that in the event you lose your job due to a layoff or injury. To that end, make it a goal to save at least six months of income in your emergency fund while in your 30s. Why six months? Studies have shown that after you lose a job, it takes around that amount of time to get a new one. Having six months’ worth of income in your savings account will ensure that you can continue to support your family while you’re hitting the pavement looking for a job.

And besides protecting you from negative events, having six months of cash in the bank gives you a bit of freedom to take some risks. Maybe you finally want to start that business you’ve been dreaming about or perhaps an opportunity comes up to travel for three months. Your emergency fund can help you take advantage of those opportunities.

In short, six months of cash in the bank is one very effective way of becoming more antifragile.

For extra personal finance points, try to save one year’s worth of income by the time you turn 40.

2. Pay off all-non mortgage debt. 

In your 20s, you paid off all your credit card debt and started a debt repayment plan for your student loans. In your 30s, the goal is to stick to that plan — keeping credit card debt at bay and paying off all your non-mortgage debt. Be aggressive with it. Slash your expenses with frugal living, earn extra money through side hustles, and divert as much of your savings and income as possible towards eliminating your student loans and any other debt. If you don’t think it’s possible to pay off your debt while trying to support a family with an average income job, just read the experiences of folks who followed Dave Ramsey’s Total Money Makeover program. You’ll find several examples of families of five or six, where the husband was the sole full-time income earner, who still managed to pay down down six-figures of debt in just a few years. It just takes dedication and sacrifice.

3. Increase retirement savings to at least 15%. 

Hopefully by now you have some sort of retirement account set up and are making regular contributions to it; you won’t be one of the 40%(!) of Baby Boomers who have nothing saved for their golden years. As you pay off more of your debt, start shifting some of the money that’s no longer going to loans to your retirement account. Most personal finance experts agree that in your 30s you should be saving at least 15% of your income for retirement. If you want to make sure you have plenty, aim for 20%. Don’t know what to invest in? Check out our post on index funds — the best stock market investment option for just about everyone.

4. Get your estate planning in order. 

You’re going to die someday. Could be in 50 years or it could be tomorrow. Whenever it happens, your estate will have to be set in order and distributed to your survivors. If you want to control how your stuff gets doled out when you’re gone and make the process as hassle and conflict-free as possible for your loved ones, you’ll need to have a will or a trust in place. Wills and trusts are particularly important if you have children. If you and your wife both die, who do you want to take care of them? How do you want the money in your accounts spent to raise them? In addition to a will or trust, your estate plan should have documents like an advance directive and durable power of attorney. Instead of your family arguing about whether to pull the plug on you when you’re in a coma, make that decision yourself with a living will and a health care surrogate designation (the person who gets to call the shots when you’re incapable of doing so).

For more information, see our article on estate planning.

5. Consider term life insurance. 

When you’re in your 30s, you’re starting to build up a financial foundation that permits you to give your family comfort and security. But what would happen if you died tomorrow? Would your family still be able to live comfortably or would they be scrambling to figure out how to make ends meet because you’re no longer around to provide for them?

Take a step to ensure your family is taken care of by purchasing term life insurance.

It’s key that you make sure the life insurance policy you get is term life insurance. There’s another type of life insurance out there called cash value or whole life policies that are much more expensive and confusing; it lasts for your entire life, and you have to pay into it until you die. With term life insurance, on the other hand, you pay a monthly premium for a set term (could be 10, 20, or 30 years). If you die within the term, the insurance company will pay out a specified amount to your beneficiaries. So for example, if you bought a $500,000, 20-year term life insurance policy, if you kicked the bucket 10 years after purchasing the policy, your wife (or whoever you set as the beneficiary) will get $500,000 from the insurance company.

Most people don’t buy life insurance because they think it costs too much. But as financial planner Jeff Rose wrote in a previous post:

Not true! A healthy 35-year-old man can get $500,000 of term insurance for 20 years for the price of 6 Double-Doubles per month at In-N-Out Burger. While you won’t get the same immediate gratification when making the payment, you can rest assured that your family is taken care of.

And what if you outlive the term of the policy? Well, congratulations! You’re still alive. That’s great news. Hopefully, you’ve been saving enough during that time that you’ll have so much money that you won’t need another insurance policy to take care of your loved ones after you die of old age.

6. Start a 529 plan for your kids. 

I don’t know what the future of higher education is going to be. Perhaps in the next 15 years, people will be able to get a college education for free online, or maybe college tuition will keep increasing at a rate of 5% each year. I’m hoping for the former, but banking — quite literally — on the latter. As soon as each of my kids were born, I set up a 529 college savings account for them to which I now make regular monthly contributions. While you can’t write off the amount you contribute to a 529 on your taxes, the interest the account generates is tax free. So if Junior’s plan earns $10,000 in interest, you don’t have to pay taxes on that $10,000 when he starts withdrawing money to pay for school.

If your child decides not to go to college, you can re-assign the account to another child and pass along the tax-free earnings. If that’s not an option, you can cash the account out but pay a 10% penalty on the earnings accrued.

7. Get an accountant (if your finances are complex). 

When you were in your 20s, your finances were probably rather simple. You may have had just a checking and a savings account and maybe a few bills. When you get into your 30s, your finances start getting more complex — mortgages, homeowners insurance, multiple retirement accounts, college savings plans, maybe even a side-hustle business. All these additions to your financial picture will definitely make taxes more complicated. While you can use software to guide you through the process, a certified personal accountant can make sure you’re not paying more in taxes than you should be and will save you a ton of time — especially if your finances are a little more complex than the average joe’s.

Up until a few years ago, I did my own taxes with TurboTax. With expanding business and financial complexities, taxes took me forever, and I was definitely leaving money on the table. So I decided to hire an accountant, and it is easily one of the best decisions I’ve ever made. She quickly found places where I was overpaying on taxes. Best of all, I hardly spend any time on my taxes myself. Just a few minutes gathering forms for her and then reviewing them before I send them in.

Listen to our podcast with Nick Maggiulli about the 6 levels of wealth and how to reach them:

With our archives 4,000 articles deep, we’ve decided to republish a classic piece each Sunday to help our newer readers discover some of the best, evergreen gems from the past. This article was originally published in November 2015.

This article was originally published on The Art of Manliness.

You’ve heard the advice that to build wealth, you need to earn more, spend less, and invest consistently. But what if there was a clearer way to understand exactly where you stand financially — and what steps you should take to reach the next level?

My guest, Nick Maggiulli, offers just such a framework. Nick is the creator of the Of Dollars And Data blog, the Chief Operating Officer at Ritholtz Wealth Management, and the author of The Wealth Ladder. Today on the show, he unpacks the Wealth Ladder concept, taking the complex, often overwhelming concept of personal finance and distilling it into six easy-to-understand wealth levels, each tied to specific net-worth milestones and financial freedoms.

Nick walks us through each rung of the Wealth Ladder, from getting out of financial instability to achieving restaurant and travel freedom, and eventually reaching upper levels of significant financial independence. We discuss the distinct strategies you should utilize on each rung to make the most of that level and move on to the next. And we get into why your spending decisions should be based on your net worth rather than your income, how wealth allocation changes dramatically as you climb the ladder, and why increasing your earning potential becomes more important than penny-pinching as you progress.

Whether you’re just getting started or well on your financial journey, this episode provides actionable insights and practical wisdom for climbing the Wealth Ladder and securing a life of greater freedom and fulfillment.

Resources Related to the Podcast

• Nick‘s previous appearance on the AoM podcast: Episode #836 — Data-Backed Answers to Personal Finance Controversies
• Nick‘s previous book: Just Keep Buying: Proven Ways to Save Money and Build Your Wealth
• Nick‘s article: What is Coast FIRE? The Ultimate Guide to Semi-Retirement
• The Missing Billionaires: A Guide to Better Financial Decisions

Connect With Nick Maggiulli

• Of Dollars and Data blog
• Nick on X
• Nick on LinkedIn
• Nick on IG

Listen to the Podcast! (And don’t forget to leave us a review!)

Listen to the episode on a separate page.

Download this episode.

Subscribe to the podcast in the media player of your choice.

Read the Transcript

Brett McKay: Brett McKay here. And welcome to another edition of the Art of Manliness podcast. You’ve heard the advice that to build wealth, you need to earn more, spend less, and invest consistently. But what if there was a clear way to understand exactly where you stand financially and what steps you should take to reach the next level? My guest, Nick Magiulli, offers just such a framework. Nick is the creator of the Of Dollars and Data blog, the chief operating officer at Ritholtz Wealth Management, and author of the Wealth Ladder. Today on the show, he unpacks his wealth ladder concept, taking the complex, often overwhelming realm of personal finance and distilling it into six easy to understand wealth levels, each tied to specific net worth, milestones and financial freedoms. Nick walks us through each rung of the wealth ladder, from getting out of financial instability to achieving restaurant and travel freedom and eventually reaching upper levels of significant financial independence. We discuss the distinct strategies you should utilize in each rung to make the most of that level and move on to the next. And we get into why your spending decisions should be based on your net worth rather than your income, how wealth allocation changes dramatically as you climb the ladder, and why increasing your earning potential becomes more important than penny pinching as you progress.

Whether you’re just getting started or well on your financial journey, this episode provides actionable insights and practical wisdom for climbing the wealth ladder and securing a life of greater freedom and fulfillment. After the show is over, check out our shownotes at AOM/Wealthlad. All right, Nick Magiulli, welcome back to the show.

Nick Magiulli: Thanks for having me on, Brett. Appreciate it.

Brett McKay: So I had you on last time to talk about your book, Just Keep Buying, which is all about, you just got to keep buying and investing in the stock market. Don’t stop. You got a new book out called The Wealth Ladder, Proven Strategies for Every Step of Your Financial Life. Really good book. I really enjoyed it. Your book is based on this idea of the wealth ladder that you’ve created. What is the wealth ladder and how and why did you come up with it?

Nick Magiulli: Yeah, so Stuart Butterfield, who’s the founder of Slack, had this three levels of wealth framework. Level one was, I don’t stress about debt. Level two was, I don’t stress about how much things cost at restaurants. And level three was, I don’t stress about how much vacations cost. And so I heard about this, oh, that’s a cool idea. At the same time, Jay-Z, you know, that he had this lyric in one of these songs. I’m not going to say the full lyric because it curses and stuff, but he just basically said, what’s 50 grand to someone like me? Can you please remind me? At the time, he had a net worth of $500 million. And so, you know, 50,000 over 500 million is 0.01% of his wealth. And so I realized, hey, that’s like a trivial amount of money to someone. So given that, I kind of came up with this levels framework, which is based on Butterfield’s three levels, but I made six levels and I actually put net worth values to them. So I’ll just walk through those just briefly. So, and just for the record, your net worth, that’s all your assets, everything you own, your cash, your stocks, your house, et cetera, minus all your liabilities. That’s everything you owe to others.

So your mortgage debt, student loans, credit card debt, et cetera. And so once you know your net worth, you’re somewhere on the wealth ladder. Level one is a net worth of less than $10,000. Level two is a net worth of 10,000 to $100,000. Level three is 100,000 to $1 million. Level four is 1 million to $10 million. Level five is 10 million to $100 million. And then level six is over 100 million. Now, once you have these levels, it’s actually funny. It actually maps up with the data and for United States household wealth, it actually maps up decently. About 20% of households are level one. So that’s less than 10,000. 20% are level two. That’s 10,000 to 100,000 in wealth. 40% of households are level three. That’s 100,000 to a million. That’s what I would call your typical middle class. And 18% of households are level four. That’s one to 10 million. That’s like upper middle class. And then over 10 million, that’s like the top 2% of households. That’s level five and six. And the nice thing about these levels, I’ve heard a lot of people do levels of wealth and do all this before.

I like this because it’s a log scale. You know, you divide by 10 or multiply by 10 to move up and down the levels. So if you know one of the levels, you can figure out the rest. So I just tell everyone, memorize level three. That’s the middle, middle class. That’s 100,000 to a million. If you know that, you can back out all the rest. And then even within that, going back to Stuart Butterfield’s three levels framework, level one was not stressing about debt, et cetera. I’ve applied spending freedoms to each level. So in my case, I said, hey, I don’t worry about what it costs at the grocery store. That’s called grocery freedom. That’s level two. So level two is grocery freedom. Level three is restaurant freedom. You don’t worry about what it costs at a restaurant, which is 100,000 to a million dollars in net worth is level three, et cetera.

Brett McKay: You can get the appetizer. You can get the Southwest egg rolls at Chili’s.

Nick Magiulli: Yeah, exactly. You don’t have to worry about any of that stuff, right? And then by the time you get to one to 10 million, you can start to have travel freedom. That’s where you can like sit in the nicer seat on the airplane. You can, stay at a nicer hotel, et cetera. You can’t really fly private yet because that’s a little too expensive. Maybe if you got to the very end of level four, I think private or travel is really reserved for people in level five. But, putting this all together is a very long answer. But putting this all together, you get the wealth ladder, which is just a new framework for thinking about money and how you make various money decisions. You can help with spending decisions, income decisions, investment decisions and more.

Brett McKay: One of the interesting things you do with the wealth ladder is you argue that this is a better way to think about how you spend money. So I think typically when people think about how they spend money, they think about their income. Well, if I’m making more money this year, I can spend more money. You argue that we shouldn’t be doing that. Instead of spending money based on our income, you say we should spend based on our net worth, which you call wealth. Why is that? Why should we base our spending decisions on our net worth slash wealth?

Nick Magiulli: Well, I think the issue is that wealth is generally less fickle than income. I mean, you can lose your job at any moment. And now, okay, I’m assuming that’s how most people earn their income. So if you lose your job, your income basically goes to zero. It’s unlikely your wealth is just going to go to zero out of nowhere. Even during the financial crisis, as bad as it was, people were seeing their homes drop by 25%, their stock portfolio get cut by 50%, which is still bad at the worst moment, but it didn’t go to zero. So it’s a little bit more stable. As a result, I think your marginal spending decision should be based on your wealth, not your income. And then what we talked about, like just the example you gave, oh, I’m at Chili’s, I want to get these egg rolls. They’re going to cost me an extra 15 bucks. Can I buy those? And I say, yeah, if you’re in level three, which is anywhere from $100,000 to $1 million in net worth, you can afford that, quote, splurge or that marginal choice to spend the $15 on egg rolls.

I don’t think it’s a big deal. And so where does that come from? It comes from what I call the 0.01% rule. And that’s kind of comes from that Jay-Z thing where it’s like Jay-Z could drop 50 grand like nothing. Well, if you have a net worth of $100,000, you can drop 10 bucks like nothing. That’s the equivalent difference, right? Obviously, we’re not Jay-Z, so we can’t drop 50K, but he also had 500 million at the time. So that’s where I start thinking about this. Like, hey, how much can I just drop as like a, you know, this is trivial to me. And so that number goes up over time. And so I think a lot of personal finance experts tell you, oh, you can’t spend more money, you know, don’t allow lifestyle creep. And I don’t think that’s accurate. I think you should have some lifestyle creep, but it should be based on your wealth, not your income. Because you’re right, your income could go up. And if you start spending more of it, you’re not necessarily saving anything else. You’re not building wealth. So my whole idea with this rule, the 0.01% rule, which is 0.01% of your net worth, or take your net worth and divide by 10,000, it’s the same thing.

That’s how much you can spend every day and your wealth will stay stagnant, at least on that amount. And so I think thinking about that is very helpful because that’s where you can start to realize, oh, hey, I can spend more over time, but only after I’ve built the wealth. The wealth ladder framework plus the 0.01% rule allows you to spend more over time after you’ve demonstrated financial discipline. And I think that is very important because I want people to be able to spend more money. I want people to be able to enjoy their lives more. And this is a slower way of doing that. And it’s a much better framework, in my opinion.

Brett McKay: Yeah, I love the 0.01% rule. It completely changed how I think about how I spend my money.

Nick Magiulli: That’s great.

Brett McKay: Yeah. So when you say this 0.01% rule, you spend 0.01% of your net worth, you mentioned earlier net worth is your assets minus liabilities. But some assets, like your home, is not liquid. It’s not tied up in cash. So should you spend the 0.01% rule, like including the value of your home, or should it just be like liquid assets?

Nick Magiulli: Yeah, so I think in general it should be liquid assets. I just use, you know, when I talk about the wealth ladder in general, I use total net worth. But you’re right when we’re talking about spending decisions, like you can’t eat your home equity necessarily. Like, yes, you can get something called a HELOC, a home equity line of credit, and you can borrow against your home and do all that stuff. So technically you can pull some of that money out, but I don’t recommend it necessarily. So I think the thinking is, yeah, what’s my liquid net worth? That’s the more conservative thing. So if like, oh, if my liquid net worth, if I have like, let’s say, I don’t know, $100,000 on a brokerage account, then you’re in the beginning of level three. That doesn’t mean you can go and splurge everything at a restaurant, but you can start to spend a little bit more at a restaurant. And where that 0.01% comes from, it’s just, obviously I just came up with this as a trivial amount, but if we assume your wealth is earning 0.01% per day, over the course of a year, if you do that, 365 times, that’s 3.7% a year, which is a conservative return.

That’s basically the assumption. I’m assuming all wealth is growing at 3.7% after inflation, like on average. I don’t think it’s a crazy assumption. And because of that, I’m just assuming your wealth can throw that off just indefinitely.

Brett McKay: Yeah, what I love about the 0.01 rule about spending on your wealth is that it’s actually kind of encouraged me to spend a little bit more. I tend to be tight-fisted and very frugal. I still think I’m a law student, broke. And it’s a good paradigm for helping me loosen up a bit. So you have a chapter about how you earn your way up the wealth ladder. So in order to accumulate wealth, you have to make money. So what does that look like? I mean, what I love about your work too is on your blog, Dollars in Data, within your other books you’ve done as well, is you’re very data-intensive. So you’re looking at all these obscure economic reports. When you look at the data, how do people on the different rungs of the wealth ladder earn money to get to that point?

Nick Magiulli: Yeah, so in general, across the wealth ladder, people in levels one to three, so that’s anywhere from less than $10,000 all the way up to $100,000 to a million, they basically earn all of their money through work. That’s how most people earn their money, right? It’s through their labor. It’s once you start to get into level four, and that’s $1 million to $10 million, and obviously you have some money invested, but we start to see a shift where assets are producing more of their income. And then by levels five and six, it’s even higher and higher. People in levels five and six get most of their income from some sort of business or assets they own, not necessarily their actual labor that they do, like the work they do. And so I think that’s the big mindset shift, and it takes time too, by the way. Like, I’m going to, we can talk about this a little bit, but the median age of a household in level four, once again, level four is one to 10 million, the median age is 62. So if we put every household in America in a room that had one to 10 million, and we just took like the middle age, basically, they’d be 62 years old.

So this is not something that’s going to happen overnight. It takes a lot of time in general or a lot of work. You know, there’s a lot of other ways you can do it, but, less than 1% of households in level four or above are under 30. So that is not the case. That’s a very, very rare thing. So when you look at how people earn money, for most people, it’s just, you know, they work and they earn money and that’s it. But as you kind of move up the wealth ladder, you start to see that those people are earning money off of their assets and not just their labor. And so that’s the big kind of mindset shift I think you need to have. And it’s what I wrote about in Just Keep Buying, right? It’s the continual purchase of a diverse set of income producing assets. That’s the mantra, Just Keep Buying, and that’s kind of what I push for. But it gets even more extreme at the higher levels of wealth.

Brett McKay: Yeah, I think that’s a good point to make. Most people don’t make it to millionaire status until their 60s. I mean, I think the problem with social media is that bias, that recency bias where you see, oh, these people who are in their 30s and 40s, just tons of money. And like, well, that’s not me. And what’s wrong with me? It’s like, well, nothing’s wrong with you, actually. You’re probably doing just fine.

Nick Magiulli: Exactly. Yeah. I think the media does a really bad job of hiding. But then again, that’s the point, I guess, is they want to show exceptional stories. They don’t want to show the ordinary things. Like, oh, yeah, I worked for 30 years and saved my 401k and now I’m a millionaire. That’s not as exciting for people, even though that’s more realistic.

Brett McKay: Another point you make in this earning up the wealth ladder is, okay, we talked about wealth is more important than income, but you show the data that income is pretty correlated to wealth. You had that really interesting chart there. Can you walk us through that?

Nick Magiulli: Yeah, so basically the idea is that within each wealth level, the median income is just increasing across each wealth level to the point where it’s the strongest relationship in personal finance. And if you really think about it, it’s like a flywheel. Your income creates wealth, and then if you obviously save and invest that, that can create more income, and then it just keeps happening over and over. It’s like the snowball. And so if you just look at the median income within each wealth level, it just goes up. So in level four, $1 to $10 million in wealth, the median income is almost $200,000. And so that’s a big piece of this, right? And then by level five, I think it’s like $750,000 or something like that, something close to that. So it’s just like it goes up, and then level six is $4.3 million. So the people in level six that have $100 million in wealth, it’s just their incomes are just super high because they’re earning so much off their assets.

Brett McKay: Yeah, I think that’s an important point because I think oftentimes personal finance advice that you see out there, popular personal finance advice, it’s geared more towards reining in spending as opposed to increasing income. And we’ll talk about this later. I think we’re going to talk about each individual rung on the wealth ladder and your different strategies to take towards it. Early on, if your net worth is less than $10,000, then yeah, you need to be concerned about how much you spend. But once you reach a certain point, it’s not so much your frugality that’s going to get you to the next level. It’s just you got to increase the amount of money you’ve got coming in.

Nick Magiulli: Exactly. I think cutting spending is a short-term decision. It can help, but the long-term solution is to raise your income, and that’s what all of the data has shown me.

Brett McKay: Yeah, I often fall back to when I’m feeling like, oh, I need to do something. It’s like I want to cut spending. I think people fall back to that because it’s easy. It’s like I can do something right away. I can stop the streaming service. I can stop going out to eat. Trying to figure out how to make money, that can be intimidating for a lot of people.

Nick Magiulli: I agree. It’s much tougher. I mean, it’s a much longer-term process. You’re thinking about, oh, do I need to learn new skills? Do I need to start a side hustle? Do I need to get some sort of credentials or education? And those are much bigger lifestyle decisions than just, yeah, I cannot go out tonight or I can kill my Netflix.

Brett McKay: Okay, so to go up the wealth ladder, you need to earn more money, and there’s different ways you can do that. We’ll get into the specifics here in a bit. At a certain point in your wealth journey, hopefully you’ll be starting to save money. That’s how you build wealth, and you’re going to put that savings into assets that make money, like investments and stocks and things like that. Talk to us about the research that you did. That was really interesting. How asset allocation changes as you move up and down the wealth ladder. What does the research say there?

Nick Magiulli: Yeah, so the data suggests that those lower on the wealth ladder, so those in like let’s say levels one to three, tend to have more of their assets in cash, their vehicle, and their home. And those higher on the wealth ladder, so that’s like those in let’s say levels four to six, tend to have more of their total assets in income-producing assets, so that’s things like stocks, bonds, real estate, and their own businesses. And so, in other words, like those lower on the wealth ladder own fewer income-producing assets than those higher on the wealth ladder. And on average, it’s like, if I remember correctly, those in levels one to three have less than 25% of their assets in income-producing assets, but those in levels four to six have over half of their assets in income-producing assets. So that’s like the main difference between those lower and higher on the wealth ladder. Obviously like, there’s other factors that can be correlated with that, but once you have wealth, the people that have wealth tend to invest that in assets that produce more income for them, which allows them to have even more wealth, et cetera.

Brett McKay: Yeah, we can talk about your story a little bit. I mean, I know you grew up, I think like middle class, lower middle class, and you had kind of a rough childhood, but my experience dealing with people who, you know, are in that level one rung of the wealth ladder, you’d see that their assets are tied up in like physical stuff, like car, house, and in extreme cases, you see like a lot of hoarding. Like, why do you got like this like junker car, in your backyard? Like, just get rid of that. That’s what I would think. But like to them, it makes sense because it’s like, well, I don’t have cash. I don’t have any income-producing assets. I can use that junker car one day to pull a part off so I can fix my car. And you see this, they’ve done studies about this, about individuals who grew up during the Great Depression. They tend to hoard more stuff because like they grew up in a time of scarcity. I guess they couldn’t really shake that mentality, even though, they’re 80 years old and they might have a pretty substantial net worth. Like they still can’t shake that scarcity mindset.

Nick Magiulli: No, yeah, I completely get that.

Brett McKay: All right, so as you move up the wealth ladder, your assets typically should shift to income-producing assets, such as stocks, could be a business, et cetera. Let’s talk about the different, like the individual levels and talk about the strategies for it and then some of the pitfalls of these different rungs and then what you can do to, get up the next rung. Let’s start off with level one. Let’s say you’re on level one of the wealth ladder. What should be your focus in order to climb to the next rung?

Nick Magiulli: Yeah, I think you have to get to some form of safety. If we’re talking about financial safety, that either means an emergency fund. There’s other types of financial safety, like you could find people you can trust and rely on to help you get out of level one, whether that’s friends or family. So like wealth is not just financial. I think especially in level one, I think you’ve got to think about the other types of wealth you have and how you can use those to get out of level one. And the reason I say this is because, something’s amplified on every level of the wealth ladder. And I think in level one, the thing that’s amplified is bad luck. Like take someone who gets a flat tire, like for someone in level three or four, like that’s an annoyance. Oh, I have to go get my tire repaired. But for someone in level one, it could send them into a financial tailspin. If they don’t have, a way of getting to work, they could lose their job, then they have to take out debt, et cetera. Like all sorts of bad things can happen just from that one flat tire.

I mean, it’s funny you brought up the junker car. That junker car could actually be that emergency lifeline. Oh, my car broke down. I have a junker I can take for a week while that one gets repaired or while I have to wait to save money so that one could get repaired. So I actually, I understand the hoarding a little bit because it is a form of safety if you really think about it, right? And so I think if you actually look at the data, like just not getting into a financial tailspin, a hole, whatever you want to call it, is like the most important thing in level one. Because over, if you look at the data, over half of the financial distress events, like bankruptcies, delinquencies, et cetera, is committed by just 10% of the U.S. Households. So it’s a very small percentage of households that are getting caught up in the same financial problems over and over again, and it’s very difficult to get out once you’re in there. So the whole point is to avoid that as much as possible. So once again, goal in level one is to get to safety.

Brett McKay: Yeah, I’ve seen that play out in my church congregation. There’s a lot of individuals who’ve just got a hard time financially, and you see like a messed up car, it just disrupts their life completely because they can’t get to work, and then they end up getting fired. And then in order to fix the car, they got to take out a payday loan because they don’t have the emergency fund to pay for the repair. And so they’ve got this crazy loan with this insane interest rate that just puts them more and more into a hole. And you got this great quote about poverty from William Volman. It says, “Poverty is wretched subnormality of opportunity and circumstances. Like, man, that’s true.

Nick Magiulli: Exactly. No, I love that quote from him, and I just think, you know, I didn’t grow up in level one, I would say. Even though my parents declared bankruptcy like twice before I was 18, I think I was in level two. I mean, just from, we had family, we had people we could rely on and stuff, so I’ve never been in true poverty. But like, yeah, we just never had a lot of money going around. So I kind of know what it’s like to grow up like lower middle class to middle class depending on what time in my life.

Brett McKay: Okay, so level one, this also sounds like where you should think more about your spending. This is when cutting spending would be the most useful strategy if you’re in level one.

Nick Magiulli: Yeah, if you can’t, obviously, raise your income is the long-term solution. But like, when you’re in a, you know, I think the tagline for that chapter in the book is, atypical results require atypical actions. And when you’re in level one, that is not normal. And so you need to get out of that. Of course, everyone’s quote, default level. And if you have an education and you’re like, oh, I just graduated college, I’m making good money, you’re going to be out of level one before you know it. It’s just a matter of like time. So that’s what happens for most people. And I would argue you’re not even in level one if you already have a good education and everything. That’s why I said I’ve never been in level one, though my net worth obviously was zero dollars when I graduated college. So yeah, I think that’s the thing to think about there.

Brett McKay: All right. So I like that. When you’re level one, your mental framework, atypical results require atypical actions. You have to cut spending and then think about ways you can boost your income. I’m curious, like, what do you do? Let’s say you’re fine financially. Say you’re level three, level two, but you got friends and family members from that level one, you see them struggling. In your experience, what can other people, what can we do to help people get out of level one?

Nick Magiulli: I think you have to first make sure that the person wants to get out of that level, like they have a real desire. Because of course, like everyone wants more money. Like everyone like, oh, of course I’d want that. But like, if they’re not going to take any steps or actions to try and move in that direction, whether that’s like, oh, I’m trying to raise my income, I’m trying to learn, get an education, I’m trying to, if they’re not doing a lot of that stuff, then like what you can do to help is be supportive and say, “Hey, is there anything I can do to help you?” And of course, if they just, you know, oh, just give me a bunch of money, that’s not going to really solve the problem. Because if they don’t have the means to help themselves at all, they’re going to end up back in that spot eventually, right? You can give someone, you know, here’s five grand or 10 grand even, get them there. And if their income is not enough to support themselves, they’re just going to draw down on that 10 grand until they’re back at level one again, right?

So you have to, I think it’s more about thinking about finding ways to help them help themselves. But at the end of the day, they have to help themselves. You can’t force someone to try and better themselves. They have to want to do it for themselves. And so you’ll notice, I guess, when I, you know, I’ve, you know, family members, friends and stuff like this who have been in this position, and there’s a big difference between someone just asking for money and someone who’s like, I need money, but I need it because I’m trying to do all these things to try and improve my life. And you’ll know, it’s more of, you’ll know it through the relationship. So I think that’s the kind of the big thing there is to strike that balance as best you can.

Brett McKay: Yeah. All right. Let’s talk about level two. So this is, you’re making, your net worth is 10,000 to 100,000. This is grocery freedom. You can buy the Dunkaroos without worrying about it. What are the big challenges when you reach level two?

Nick Magiulli: Yeah, I think the thing to think about in level two is the trajectory you’re on and what level that’s going to get you to. Because there’s two groups of people in level two. There’s people in level two who are going to probably be there most of their life, or they might barely get into level three by the, you know, later in their life. And then there’s people in level two who are just there temporarily. They’re making good money and they’re kind of on their way to deep into level three or level four. And I think the big difference there is education and what skills you have. This is, you know, level two is the level where getting those skills can really kind of change that. You can imagine your trajectory is like a slope on a line, and that slope can be pushed upward and change your income, your career, et cetera, based on that. So it doesn’t always have to be a college degree, but I think you need something that allows you to grow your income in a big way, whether that’s, a skill that’s very useful. I think, for example, sales. If you’re a good sales person, you can make very good money, easily six 

Figures and, you know, there’s some sales people out there that make seven figures or more at the higher end, you know, they’re selling a luxury good, like high-end real estate, things like that. And so you can make really a lot of money in sales. And that’s something that AI is not going to be able to replace. I don’t think we’re going to have robot realtors or anything like that. So there are still skills out there that you can learn and you can make a lot of money that don’t necessarily require a degree, but they definitely require a lot of work.

Brett McKay: We’re going to take a quick break for a word from our sponsors. And now back to the show. Okay, so level two, your goal is just like figure out the education, the training, the skill acquisition you need in order to make more money so that you can accumulate more wealth. That’s the key there. All right, let’s talk about level three. So this is when you move to 100,000 to 1 million in your net worth. What are the big stressors there when you reach level three?

Nick Magiulli: I think the stressors are more about if you’re overspending. And the reason I say that because if you look at people and I did, there’s some data from the University of Michigan has something called the Panel Study of Income Dynamics, which just looks at the same set of households over time. So we can follow people’s career trajectory, their income, all their spending over time, we can follow it. And in that data, I said, okay, let’s look at people in level three today and look at those that made it to level four and compare it to the people that are in level three today that stayed in level three. And so what are the differences between those two groups? Like the people that went from three to four and the people that stayed in level three, let’s say over a decade. And so if you look at that information, the difference is income. That’s a big piece of it. So those that made it to level four generally earned more. But I think the bigger thing I noticed was the spending. The people that stayed in level three over time spent almost as much money as the people that made it to level four from level three.

So the people that made it to level four from level three did spend a little bit more, but not that much more than the people that stayed in level three over time and those people that made it to level four at a much higher income. So it’s like, I think the issue, the stressor in level three is that people are trying to do the keep up with the Joneses thing. They’re overspending on housing, cars, whatever to portray a certain lifestyle when they don’t necessarily have the money for it. And so they don’t have the income for it. So I think that’s the thing to focus on is like, hey, make sure I’m not overspending in this level. And then once again, I don’t think cutting spending is the way to build long-term wealth. I do think it can be something, especially on the big ticket items like housing in particular, I think is very important. You have to think about your spending there. And then in terms of what to focus on in level three, I think it’s really about your income and specifically your income from investments. That’s where as you start to invest, by the time you have a portfolio in the six figure range, that’s throwing off real money.

You know, if you have $10,000 invested and you get a 10% return, that’s a thousand bucks. That’s not really going to change your life. But by the time, you know, you have 100,000 invested or more, now it throws off that same 10% return throws off $10,000 is a much more significant change in wealth. And so I think that’s where you start to see, hey, the flywheel really starts to grow in level three and by level four, it gets even bigger. But I think that’s where you should focus, spend more time focusing on is investing in income producing assets in level three.

Brett McKay: In your research, what’s the average age for someone who’s in level three?

Nick Magiulli: So yeah, the median age in level three in the United States is 54 years old. So it’s still like, I say that’s middle class, but it’s also people who’ve been spending their life, buying their home, saving their retirement account, et cetera. It doesn’t happen overnight. And just for reference, the 25th percentile age is 40. So that means one in four households in level three are 40 or younger. So a lot of people can get to level three before 40, but it’s still rare. It’s only one in four people that get into that level are younger than 40. So something to keep in mind.

Brett McKay: Yeah. And so the tactic there is when you reach level three, your focus should start being spent towards how can I have more of my income come from income producing assets. So that’s investments. And the mental framework there is just keep buying. That’s from your first book, like just start socking away as much money as you can in your investments, because that’s going to add up over time.

Nick Magiulli: Yeah, exactly. And that’s why it’s the perfect book for someone in level three going to level four, or even kind of level two going into level three. But it’s really made to shift your mindset from just, oh, I go and I save money. I work and save money to, oh, I go and I save the money. I invest it in assets that then pay me money. And then that money can be reinvested. And it just goes from there.

Brett McKay: All right. So let’s move to level four. This is when you get to 1 million to 10 million. That’s a big range. But the point you made, though, is once you go higher and higher up the wealth ladder, an increase of just one isn’t going to be that big of a difference. If you have a million dollars and then you increase your net worth by another million, that’s a lot of money. But in the grand scheme of things, it’s not that big of a jump, really. One of the things you talk about in level four, this is the place where a lot of people, this is where they stop. This is where they stop the trek up the wealth ladder. And to remind people, meeting age for this is like 62. So this is like you’re end of your working career. And, you know, if you get to this range, like you’re probably, you’re good for retirement. Why do people get stuck on level four, though? Why don’t they continue to go up the wealth ladder?

Nick Magiulli: They get stuck in level four because the actions that get you into level four aren’t the ones that get you out of level four. There’s this Marshall Goldsmith book called What Got You Here Won’t Get You There. It’s a career book. It’s about career strategy. Now you have to change your career strategy over time to get promoted and stuff. But I think it’s the same idea. You need to change your strategy if you want to keep climbing the wealth ladder. And once again, getting stuck in level four is not a problem necessarily. I think there’s a lot of people that like, great, I’m never going to get out of level four. It’s not a problem. Realize that, accept it, be happy. The simplest way I can say it. But if you do have aspirations to go beyond that, you really are in why we can get into the psychology of that. But if you do, then you have to kind of change your strategy. And for most people that get into level four, you can get into level four with a few things. You have a decent job making a good money, you’re saving that money, you’re investing it and reinvesting all that income, and enough time.

 So like job, good job plus investing plus time, and you get to level four in the United States. But to get to level five, which is 10 million plus, it’s a whole nother thing. You’re going to basically have to either start a company and basically own all the equity and sell it for a decent amount of money. Or you join a startup early, get a good amount of equity, and that company sells for a lot of money, right? You either own a small piece of something that’s very big or a big piece of something that’s decently sized, let’s say. So that’s where I think the difference is. And we can even run the math on this. I do this in the book where I’m like, hey, let’s say today you made it to a million dollars. And let’s just say you have a portfolio, just to keep it very simple. You have a million dollar brokerage account that’s earning 5% a year, and you’re saving $100,000 a year after tax. That’s a considerable amount of money. Assuming that’s all true, how long would it take you to get to 10 million?

 The answer is 28 years. It’s crazy. So if you imagine the typical person gets there, let’s say it’s in their mid-50s or early 60s, do you want to grind it out for three more decades just to get to 10 million? No, you don’t want to. You’re not going to do that. No rational person would do that. They would say, hey, I’ve done enough, and they stop. Even if you’re saving $300,000 a year, which means you’re probably making close to a million bucks pre-tax and everything, you’re saving $300,000 a year earning 5%, you start with a million, it still takes you 17 years to get to 10 million. So the math is not friendly to you once you get into level four. That’s why I call it the no man’s land on the wealth ladder. Because once you get in there, it’s hard to get out. And then succession has that joke, five to 10, five to 10 is a nightmare, right? Because it’s true. There’s no real incentive to keep working because your income is not going to really move the needle anymore.

Your wealth is throwing off so much wealth on its own. So you’re in this weird spot where you’re like, hey, I don’t know what to do here. And I think for most people, the rational response is, hey, take your foot off the gas, enjoy life more, do like a type of coast fire thing, find work you just find enjoyable and not just for money and go from there and stop worrying about getting to level four.

Brett McKay: Yeah, be okay with level four. Level four sounds pretty awesome. You mentioned coast fire. What is that? You wrote an article about that. What is coast fire for those who aren’t familiar with that phrase? 

Nick Magiulli: Yeah, sorry. I try not to use so much semantics, but coast fire, I’m assuming most of your audience heard of fire, which financial independence, retire early. Coast fire, the idea there is you save up just enough for your retirement. We’re like, hey, I have enough money now where if we assume it grows at a conservative rate, let’s say you assume it grows at 4% a year. So you say between now and when I retire, let’s say you retire at 65. So I’m 35 now, I’ll just use myself as an example. So let’s say I have enough money now where if I assume it grows at 4% a year between now and when I’m 65, 30 years from now, I’m going to have X dollars. And then at that point, I can then pull from that money and use that money to live off in retirement. That means you’ve hit coast fire once you don’t need to save any more money for retirement. That’s the point where coast fire lives. And so does that mean you don’t have to work anymore? No, because you still need to cover your current consumption.

You’re not supposed to use your assets to cover your current consumption. You’re supposed to use any income you have to cover your current consumption, but it means you don’t have to save more for your future. That’s kind of the big difference in thinking here. And so I think coast fire is actually the exact place for it is level four, because people will get there and say, hey, and especially if you get there like relatively younger, like let’s say in your 40s or something, you might be like, hey, this is a time for me to like, I can take my foot off the gas, I can chill out a little, and I can work on something that’s maybe more meaningful to you or maybe doesn’t make you as much money. And you don’t have to worry about saving as much. You just need to cover your current expenses. And the rest will take care of itself, basically.  

Brett McKay: Yeah, or I mean, even if you get there when you’re in your 60s, so you have a long, productive working life, you save for retirement, and you don’t have to work full-time anymore. But you could still get a part-time job if you wanted in your 60s. My dad, he did that. He had a government job, forced retirement in his early 50s because he was in law enforcement. And he’s got a pension. He didn’t have to work, but he kept working. He took contract work, and he’s still working. He’s like 70. I think he’s like 75. Still works, and he enjoys it. But I think it covers my parents’ consumptive costs.

Nick Magiulli: Yeah, that’s great. That’s how I think a lot of people should do it. And I think we always look at work as like, oh, wouldn’t it be great if I never had to work again? People idealize that. At the same time, I think a life without any work or any… Work doesn’t necessarily have to mean paid work, by the way. But a life without any work, I think, is a difficult life if you do it for a very long time. I think it’s very tough mentally to do that. Of course, you may reach a point in your life where you’re like, you know what, I’m happy to do that, and some people are okay with it. But I think a lot of people want to have some sort of purpose or something they’re working on. And so I’ve looked at all the research and the data on this, and overwhelmingly, people do find a lot of positive benefits from work. Now, of course, if you’re in a job you hate, you want to get out of that as quickly as you can. But for most people, you want to do something you enjoy working on, whether that’s a creative endeavor, whether that’s volunteering. The options are very numerous.

And so it’s just figuring out what you want and then building your life backwards from that.

Brett McKay: Okay, and so level four, again, this is the 1 million to 10 million range. This is achievable through increasing your income, through acquiring new skills, increasing your education, asking for raises, investing, and then just time, like the time factor. 

Nick Magiulli: Time’s a big piece of this. Once again, the median age is 62.

Brett McKay: Yeah, I think that’s an important thing. If you’re in your 30s or 40s right now, you’re like, I’m not in level four. It’s like, okay, you’re fine. You’ve got 20 years to make that happen.

Nick Magiulli: Yeah, just for the record, less than 1% of households in their 20s are in level four. Less than 5% of households in the 30s are in level four. So only like 1 in 20 people in their 30s are in level four. 15% of people in their 40s are in level four, and et cetera. And this is in the book. It breaks down by age cohort, by decade, 2029, 3039, et cetera. It shows the percentage of people within that cohort that are in each wealth level.

Brett McKay: What are the biggest risks or stressors once you reach level four, you think?

Nick Magiulli: I think the money stressors in level four are similar to level five, and I think the stress is usually from a lack of diversification. It’s like concentration, that’s the issue. As really the only way to lose wealth quickly. Obviously, there’s divorce and other things, outside factors, but if we’re just talking pure monetary factors, it’s really going to be concentration. So it’s like, how is your wealth allocated, and how concentrated are you? Because the more concentrated you are, the more likely you could lose wealth quickly. Of course, that’s also how you can build wealth quickly, but it’s a double-edged sword. And I think realizing that it’s a double-edged sword is what’s important here.

Brett McKay: All right, so diversify 

Nick Magiulli: Yeah. Yeah.

Brett McKay: Is the key there. And then, yeah, move to level five. Like you said, what got you to level four is not going to get you to level five. You’re going to have to do something radically different. And for a lot of people, that might not be rational. What causes people to, like, they reach level four, they’ve got the vacation money, they can just take a nice vacation whenever they want, life’s good. Why would someone want to make that leap to level five based on your experience interacting with people who’ve made that leap? 

Nick Magiulli: There could be a lot of different reasons. One, some people want to create really big generational wealth for their families. Some people want to fly private. Some like the ego boost of being like, oh, I’m not just upper middle class, I’m upper class, right? I’m really wealthy. I can go and buy supercars and all these other things that you see the stereotypically rich people do, which, funny enough, most rich people don’t even own supercars, right? People with that level of wealth, they don’t spend money like that. So it’s only really the media’s depiction of it that makes it look like that. So why do people do it? I mean, in the book, I say, the most expensive thing some people own is their ego. So if the most expensive thing some people own is their ego, that’s why. You know, that’s the answer, the short answer for you.

Brett McKay: Yeah. So we talked about rungs one through five on the wealth ladder. Rung six is $100 million plus. And that’s going to apply to just a very small amount of people. There’s only 11,000 households in the U.S. Who are on rung six. And these are basically people who’ve sold their businesses for huge amounts of money or, you know, like athletes or entertainers. But even very few of those people reach that level. Let’s talk about mobility up and down the wealth ladder. Let’s talk about how often people fall down the wealth ladder. Let’s say someone gets to level four. How often do they stay there?

Nick Magiulli: It’s usually pretty rare how people fall down. So for example, over a 10-year period, 11% of households fell down one wealth level and 2% of households fell down two wealth levels. This is based on the historical data where I’m following the same set of households over time. We can actually control for by level, and it’s actually a little bit more interesting because you can say, okay, hey, if I started in this wealth level, what’s the probability I’m going to be in another wealth level in the future? So for example, going to what you just asked, if you start in level four, after 10 years, there’s a 23% chance you’ll be in level three and there’s less than a 1% chance you’ll be in level two or one. So it’s very unlikely. 72% of households that start in level four are still in level four after 10 years. And that’s like the highest out there. And we can look over 20 years and it’s roughly the same. That’s why after 20 years, if you start in level four, there’s a 64% of those households are still in level four after 20 years. Only 8% make it up the wealth ladder to level five.

So it’s very rare to see that kind of mobility switching, but it does happen.

Brett McKay: What about mobility going up on those lower rungs, like from one to two to threes? That’s still happening? You hear all this talk about like the American dream is dead. There’s no income mobility or wealth mobility. What does the research say about that?

Nick Magiulli: So this research is historical. So it’s going backward looking from like, 1980s when we first had the wealth data through 2021. So the question is, is it still happening now? And will it happen in the future remains to be seen. But in general, like there is mobility. So for example, let’s just look over 10 years. If you start in level one, after 10 years, there’s a 54% chance you will be out of level one. There’s a 30% chance you’re going to be in level two. There’s a 22% chance you’ll be in level three, et cetera. So there’s a decent chance that you can kind of get out of level one and get higher on the wealth ladder. 46% of households stay in level one after 10 years, but the rest don’t. So there is mobility and there’s some healthy mobility. And it’s just, I think a lot of it’s time as well, because people get older and so they save money and they age out.

Brett McKay: Let’s talk about mobility across generations. There’s that phrase, shirt sleeves to shirt sleeves in three generations. So there’s a generation that got a lot of wealth. And then by the third generation, that generation, like the money’s just gone. There’s actually, I think there was a book that came out a couple of years ago, like where are all the billionaires? 

These guys looked at the Vanderbilt family. So like Vanderbilt, he left an inheritance, I think it was like $100 million. It’s almost like $3 billion in today’s money. But if you look at the descendants, like there’s like no more billionaires in the Vanderbilt family. What goes on there? Like why is it so hard to maintain a family on a rung in the wealth ladder?

Nick Magiulli: Well, I think there’s a lot of reasons why this is, I mean, I can talk about the Vanderbilt specifically or just like level six wealth, let’s just call it, and then compare it to other wealth levels. But in level six, so most people that have that much wealth, it’s usually concentrated. And so unless they diversify, it’s very unlikely that that’s going to last. This is why I think Bill Gates and Warren Buffett are so smart because of all the billionaires out there, they may not be the richest on the list, but they’re the most diversified. They’re the ones that are least likely to see their wealth just, disappear or see a massive change in their wealth because they’re very diversified. Like Bill Gates is the largest private landowner in the United States. He owns more US land than any other individual. So he owns a lot of different assets and things that are going to allow him to have wealth for multiple generations. And I think if you’re like an Elon Musk, even though he’s richer on paper, if something happens to Tesla, that’s like the majority of his wealth. So he could easily fall below Gates at any moment.

And so that’s a piece of it. I think if you look at like the growth of families, like they’re growing faster than the wealth is. So like, let’s say you have two kids. Now they have two spouses. That’s now four people. And then each of them have two kids, right? And so now four people is now eight people. And then those kids get spouses and they have kids, right? You can just see how it’s growing at such a fast pace and your wealth is not keeping up. So it makes sense why the Vanderbilts couldn’t do it. At just some point, like the math doesn’t make sense, So that’s another piece of it. But I think just if we’re talking about lower wealth levels, like I think succeeding generations can find it difficult to stay in the same wealth levels or parents because like economic conditions change. They may not want to work as hard. Like, oh, I don’t want to work like my parents did to get to that level. I may just realize, I don’t need to work as hard because I know I’m gonna get an inheritance so I can just chill a little bit more.

They may have different feelings about money. Like all these are very case specific, but just a few reasons that make sense to me.

Brett McKay: So we’ve talked about the different rungs of the wealth ladder. They all have their opportunities and their risks. How do you figure out like where you’re fine at? What other things should you consider besides your net worth in deciding that, I’m okay where I am at financially? What are things you consider in order to figure out if you have a rich life or not?

Nick Magiulli: I think it really depends what you want out of life. I mean, this is the most difficult part of being a human in modern civilization is like, we’ve been debating this idea since the time of the ancient Greeks. You know, it’s like why, you know, know thyself is such an important concept. And it’s because you need to know what you really want. And so once you can solve for that, then it’s much easier to figure out, okay, well, how much wealth do I need to support that? Oh, I want to, I can imagine your dream life or whatever it is, like how much wealth do you need to support that? Because once you know what you want, then you can figure out all those things. And for most people, I think it’s lower than they think. I mean, it’s always easy to justify needing more, but yeah, you have to kind of get past that or figure out what’s the things that really matter. So it’s like your time, how much free time do you have or time you can use, time wealth is what we would call it. You can think of mental wealth. You can think of physical wealth. You can think of social wealth.

All these different things, right? Sahil Bloom has a book called The Five Types of Wealth where he talks about all these. And I use that as a framework in the wealth ladder to think about these types of, you know, a rich life and what does that mean? And it also depends where you live too. Like I said, you know, 1 million to 10 million is upper middle class. Well, it kind of depends where you live. You know, if you’ve got 8 million bucks and you’re in a low cost of living area, you’re upper class. You’re actually very upper class. But if you’re in New York City, maybe not So it really depends where you live, the type of lifestyle you want, et cetera. So those are the things I would say to take into account.

Brett McKay: Yeah. Whenever I go to San Francisco, like, man, this place is beautiful. I could see myself living here. And then you look at the cost of housing. You’re like, no, I can see why housing is so expensive because it’s so beautiful. But I’ll stay in Tulsa next to the Arkansas River and take the sunsets, I guess, in Oklahoma. Well, Nick, this has been a great conversation. Where can people go to learn more about the book and your work?

Nick Magiulli: Yeah, so you can find the book everywhere books are sold, Amazon, Barnes & Noble, bookshop.org, et cetera. And you can find out more about me. I write every week at ofdollarsanddata.com. You can also find me on Twitter/X at dollarsanddata. I’m on Instagram at Nick Magiulli, and then I’m on LinkedIn at Nick Magiulli. I answer every DM. So if you have any questions or anything, feel free to DM me.

Brett McKay: Yeah, and of dollars and data, plug for that. It’s one of my favorite financial blogs out there. It’s a lot of fun to read. Well, Nick, thanks so much for your time. It’s been a pleasure.

Nick Magiulli: Thanks for having me on again. Appreciate it, Brett.

Brett McKay: My guest here is Nick Magiulli. He’s the author of the book, The Wealth Ladder. It’s available on amazon.com and bookstores everywhere. You can find more information about his work at his website ofdollarsanddata.com. Also check out our show notes at aom.is slash wealth ladder. You can find links to resources and we delve deeper into this topic. Well, that wraps up another edition of the AOM Podcast. Make sure to check out our website at artofmanliness.com where you can find our podcast archives. And while you’re there, sign up for our newsletter. We got a free newsletter on Art of Manliness. There’s a daily and weekly version. It’s the best way to stay on top of what’s going on at AOM. And if you haven’t done so already, I’d appreciate it if you’d take one minute to give us a review on Apple Podcasts or Spotify. It helps out a lot. And if you’ve done that already, thank you. Please consider sharing the show with a friend or family member you think of something out of it. As always, thank you for the continued support. Until next time, it’s Brett McKay. Remind you not to listen to the AM1 Podcast, but put what you’ve heard into action.

This article was originally published on The Art of Manliness.

You’re hunched over the kitchen table, flipping through your job’s benefits packet. You see something about a Health Savings Account. Looks like a boring place to stash medical cash. You shrug and skim past.

That could be a big mistake — not marking that little checkbox could cost your future self a six-figure windfall.

If you’re looking for an easy way to maximize your money, allow me to introduce you to a stealth wealth builder: the health savings account or HSA.

I’ve had an HSA since Kate and I first got married. But it wasn’t until fairly recently that I started to realize what an underrated finance tool this thing is.

Today, I’m going to walk you through the benefits of a health savings account and why you might consider opening one up.

HSA Basics

A Health Savings Account is a special kind of savings account designed for medical expenses — but it does a lot more than that. An HSA lets you set aside money tax-free, grow it in the stock market tax-free, and use it for healthcare costs now or decades down the line (yes, tax-free!).

To qualify for an HSA, your health plan needs to have a high deductible — the amount you pay out of pocket before your insurance starts covering costs. As of 2025, the IRS defines a high deductible as at least $1,650 if you’re single or $3,300 for a family. The out-of-pocket max can’t exceed $8,300 or $16,600, respectively.

You can use HSA funds to pay the deductible and any other qualifying medical expenses your insurance doesn’t cover.

You can contribute up to $4,300 a year to your HSA as an individual or $8,550 for a family. If you’re 55 or older, tack on another $1,000. The IRS updates these numbers every year.

HSAs often get confused with FSAs. FSA stands for flexible spending account. FSAs let you set aside pre-tax money from your paycheck to cover qualified out-of-pocket healthcare costs, like copays, prescriptions, and medical supplies. Because the money isn’t taxed, it lowers your taxable income and saves you money. But here’s the catch with FSAs: most FSAs have a “use it or lose it” rule, so you need to spend the funds within the plan year or risk forfeiting what’s left.

This is a big difference between HSAs and FSAs: with HSAs, the money doesn’t vanish if you don’t spend it. It’s yours; it rolls over forever, and you can invest it in the stock market.

Why the HSA Is an Awesome Wealth-Building Tool

The tax savings are huge. The big reason the HSA is such an excellent wealth builder is that it functions like a legal tax shelter.

It offers three big tax benefits:

First, contributions you make to the account are deductible. When you put your money into an HSA, you lower your taxable income. So if you invest $8,550 into your HSA, you reduce your taxable income by $8,550 for the year.

Second, the investments you have in your HSA grow tax-free.

Third, if you use the funds in your HSA for medical expenses, the withdrawals aren’t taxed. So you can pay for braces, doctor appointments, and prescriptions tax-free with money that hasn’t ever been taxed.

All those tax savings really add up and keep money in your pocket where it belongs.

It is possible to use the money in your HSA for non-medical expenses, but that’s not an advisable move, as you’ll have to pay taxes on the amount you used and pay a 20 percent penalty. So, for example, it you withdrew $3,000 from your HSA to pay for a car repair, you’d have to pay income tax on that $3,000 plus an additional $600 (20% penalty). Don’t do that!

The HSA is an inflation-busting healthcare savings builder. An HSA can be a great tool to save on taxes on your immediate healthcare expenses. But where it becomes really powerful is in its ability to help you pay for healthcare expenses decades down the road, when they will likely be higher.

If you’re young and healthy, you probably won’t have to tap into your HSA all that much. This means the money invested in your HSA can take advantage of the power of compounding and grow tax-free for years. This allows you to build an inflation-proof (an HSA can be invested, and investments typically grow faster than inflation) healthcare war chest for the period in your life when medical expenses rise the most: elderhood. Fidelity estimates that a 65-year-old couple will spend $330,000 on medical costs in retirement. That doesn’t even count long-term care. An HSA gives you a way to prep for that monster bill using pre-tax dollars and tax-free market returns.

You can turn an HSA account into a stealth retirement account. An HSA can provide immediate tax savings and help you grow your money for long-term healthcare costs tax-free.

But here’s another cool thing about HSAs: you can turn them into a retirement account when you turn 65.

Once you reach that age, the 20 percent penalty that normally applies to non-medical HSA withdrawals disappears. At that point, you can tap the account for anything — travel, groceries, a new fly rod — and the distribution is simply added to your ordinary income for the year, just like pulling money from a traditional IRA.

The tax-free treatment for qualified medical expenses, however, still applies, so it’s usually smartest to keep using the HSA for healthcare and let other accounts fund your lifestyle. But it should give you some peace of mind knowing that you have another retirement account you can tap into in your golden years.

An HSA is portable and inheritable. You can’t lose your HSA if you change jobs or health insurance plans. It stays with you no matter where life takes you.

When you die, your spouse can take it over tax-free. If it goes to someone else (like a child or grandchild), it’s taxed but not penalized — same as an inherited IRA.

How to Get the Most Out of Your HSA

I hope by now you can see how awesome HSAs are. If it’s an option for you, I definitely recommend opening one up. You can do so through a provider like Fidelity or your employer’s chosen custodian and start contributing funds either directly or through payroll deductions.

Once you’ve got an HSA going, you can get the most out of it as a wealth-building tool by doing the following:

Invest the balance once you’ve cleared the provider’s cash threshold. Most HSAs require you to have a minimum amount in cash. Once you hit that minimum, invest the rest in index funds. This will help your money grow faster.

Do all that you can to leave the money in your HSA alone. That means paying for as many of your medical expenses as you can out-of-pocket. If you’re young and healthy, that likely won’t be too much of an issue. If you or a family member has a chronic health condition, it will be harder. Do what you can based on your situation.

The reason you want to leave the money in your HSA alone is that it allows your money to grow tax-free.

When you do pay for medical expenses out-of-pocket, hold on to those receipts. You can reimburse yourself (tax-free!) from your HSA decades later.

So if you paid $1,000 out-of-pocket for an ER visit in 2025, you can reimburse yourself that $1,000 expense from your HSA tax-free in 2045. During that time, the money in your HSA has been growing tax-free. That $1,000 you would have spent in 2025 from your HSA might be worth $3,000 in 2045 — letting you keep the investment gains and still get reimbursed, effectively turning a medical bill into a wealth-building opportunity.

Hopefully, by now, you can see that an HSA is more than just an account to pay for this year’s doctor’s visits. When used strategically, it’s a long-game wealth builder that saves you in taxes and gives you options down the road.

This article was originally published on The Art of Manliness.

What if the traits you’ve been taught to suppress your entire career are actually the very qualities that separate those who get what they want from those who stay stuck waiting for recognition that never comes?

Today on the show, Jenny Wood argues that most of us are living in what she calls “an invisible cage” created by an overabundance of caution, and that the biggest lie you’ve been told in your career is to keep your head down and let your work speak for itself.

Jenny is a former Google executive who developed a career development program used by 56,000 people in nearly 100 countries, and she’s the author of Wild Courage: Go After What You Want and Get It. In our conversation, Jenny explains how traits that have a negative rap can be used for positive ends that will advance your career. We discuss how being shameless, reckless, nosy, manipulative, obsessed, and more can help you overcome your success-hindering fears, take bolder action, and achieve your goals.

Connect With Jenny Wood

• Jenny’s website

Listen to the Podcast! (And don’t forget to leave us a review!)

Listen to the episode on a separate page.

Download this episode.

Subscribe to the podcast in the media player of your choice.

Read the Transcript 

Brett McKay: Brett McKay here, and welcome to another edition of the Art of Manliness Podcast. What if the traits you’ve been taught to suppress your entire career are actually the very qualities that separate those who get what they want, from those who stay stuck waiting for recognition that never comes? Today on the show, Jenny Wood argues that most of us are living in what she calls “an invisible cage” created by an overabundance of caution, and that the biggest lie you’ve been told in your career, is to keep your head down and let your work speak for itself. Jenny is a former Google executive who developed a career development program used by 56,000 people in nearly 100 countries. And she’s the author of “Wild Courage: Go After What You Want and Get It.” In our conversation, Jenny explains how traits that have a negative rap can be used for positive ends that will advance your career. We discuss how being shameless, reckless, nosy, manipulative, obsessed, and more can help you overcome your success-hindering fears, take bolder action, and achieve your goals. After the show’s over, check out our show notes at aom.is/wildcourage.

All right, Jenny Wood, welcome to the show.

Jenny Wood: Thanks so much for having me, Brett.

Brett McKay: So you were a successful Google executive. While you were there, you also developed a career development program that helped employees advance their careers by learning how to advocate for themselves, stand out for the crowd. So you’ve made a career for yourself by being unapologetically ambitious, like going after what you want. Have you always been like that? Were you like that as a kid, or was there a moment in adulthood where that switch finally flipped and you’re like, all right, I’m gonna start turning my ambition into action?

Jenny Wood: Ooh, there was a moment, Brett. There was a moment, and it was in 2011 on the New York City Subway, when I was riding the subway home from work, and about 20 feet away from me stands this really good-looking guy, gorgeous blue eyes, thick brown wavy hair, the whole works. And even though I wanted to talk to him, something held me back. The things you would normally think about some stranger on the subway. What if he’s a convicted felon? What if he’s married? What if 100 people stare at me on this packed train? So I sit there, I do nothing while the train passes stop after stop after stop, and his life, frankly, passes me by. But I’m so taken by him that I make a deal with the universe, and I say, if he gets off at my stop, then maybe I’ll try to strike up a conversation with him. And if not, c’est la vie. Well, he gets off at the next stop, which was not my stop, and just as the doors are about to close, I feel this wave of wild courage wash over me and push me out of my subway seat and off the train.

I chase to catch up with him, tap him on the shoulder. I say, excuse me, I’m sorry to bother you, but you were on my subway and I thought you were cute. You’re wearing gloves, so I can’t tell if you’re wearing a wedding ring, but in the event that you’re not married, any chance I could give you my business card? And then I wait for what feels like forever for him to take my card, thinking this was a terrible idea. But he does take the card. He calls the next day. We go on a date a week later, and we’ve now been married for 11 years with two small kids who are nine and seven.

Brett McKay: No, I love that story. I love how you started your book off with that story, ’cause that really captures the title of the book, Wild Courage. So what were you like before that moment? Were you sort of just someone who played it safe, tried to stay in the background?

Jenny Wood: Yeah, I was a confident Google employee on the outside, but scared and timid on the inside, always worried about what my boss was going to think about me walking out of our Tuesday one-on-one, always concerned that nobody would forget that one client presentation I flubbed, always nervous about when I eventually had direct reports and indirect reports as a Google exec, what they thought about me and how they were gonna score me as a leader at Google because there’s a lot of upward and sideways and downward feedback at Google. And it’s funny, just yesterday I gave a keynote to a Google team that happens to be led by the guy who hired me at Google almost two decades ago. And he’s like, Jenny, it’s so interesting and wonderful to see you come into your own because when you first started, you had a hard time having a perspective. You had a hard time sharing your thoughts. I knew that you had smart ideas, but you were too nervous and timid and held back to share those out loud for business impact. And I was like, wow, it’s so interesting because sometimes I think people push back on me and they’re like, it seems like you were just born this way, Jenny.

You seem really confident. You could sell ice to Eskimos. And it was such an interesting moment when I was doing this talk and getting this feedback from the guy at Google who hired me to realize like, yeah, I was not born this way. And you don’t have to be either. You might not be a subway chaser, but wherever you are sitting right now, there is something that you want. And wild courage is what closes the gap between what you want and what you get. And it’s this set of tools that help you go after those things and get them. And it can be learned. It is not an innate skill. It takes practice, it takes reps. It takes building the muscle of wild courage.

Brett McKay: And as you described yourself in the book before you made this jump to wild courage, you remind me of, I was like this in high school too. Correct me if I’m wrong. This sort of describes you how you were in high school and college. You worked hard, you were quietly ambitious, you kind of just like, I’m gonna work really hard, do my best, and then I’ll just wait for people to notice.

Jenny Wood: Yeah, exactly.

Brett McKay: And then if people notice me, then okay, that’s fine. But if they don’t, I’m just gonna stay in the background. I think there’s a lot of people like that. They’re really conscientious. They do good work, but they wait for people to notice before they actually put themselves out there.

Jenny Wood: Absolutely. I was like that. I would almost take it a step further and say that I was really hesitant to stand out, even to acknowledge my own ambitions or share them.

Brett McKay: Yeah, you have this great line in the book that says, “Most existential anxiety in life isn’t about a lack of ambition, but an overabundance of caution.” So the book’s called Wild Courage. What makes wild courage wild?

Jenny Wood: Well, wild courage consists of nine traits that create the bars of an invisible cage that keep you small, that keep you quiet, that keep you following instead of leading. And my goodness, do they raise eyebrows. They are weird, selfish, shameless, nosy, obsessed, manipulative, that’s a spicy one, brutal, reckless, and bossy. And those are not traits we typically think we want to aspire to. So that is the wild piece of it.

Brett McKay: Okay, so your traits of wild courage are weird, selfish, shameless, nosy, obsessed, manipulative, brutal, reckless, and bossy. And what you do in the book is you reclaim these words, which they typically have a bad rap, and you reframe them with new definitions and lay out how they can be used for positive ends. And you say people can use these traits to overcome the three fears you think hold people back. It’s the fear of failure, the fear of uncertainty, and the fear of judgment of others. So let’s talk about some of these traits. The first one is weird. This is all about standing out. Why is learning to stand out such an essential skill and trait to develop if you want success in life?

Jenny Wood: Yeah, well. The world is just too busy and competitive for you to be invisible and make a dent in your career or in your life. So weird is about having the courage to stand out and be authentic, because within your so-called weirdness lie your greatest strengths. So hone every ounce of weird you’ve got. And that might be what I call playing it hot, which is respectfully disagreeing with your boss in a one-on-one, or sitting in the front row of your VP’s presentation, or being the first person to raise your hand and ask them a question. Or actually, you referenced this program I started at Google called, Own Your Career. That was kind of weird. I played it hot. I did not ask for any permission. This was not my full-time job. I ran an operations team that sat between sales and engineering and helped drive billions of revenue for the company annually. But people would come to me for mentorship, and this guy came to me, and he was asking, he was one of the many people who came to me for mentorship, and was asking, hey, how do you navigate entry-level to executive here?

And I was like, okay, let me just scale this. Let me write down 10 tips that made me successful here, everything from navigating politics, to stakeholder management, to influence skills, to getting promoted. And I’ll just put together a quick training. I’m sure that maybe 30 people will come. Well, 2,000 people came to that first training, and that grew into Own Your Career, which was used by 56,000 people in nearly 100 countries. But here’s the thing. I was playing it hot. I was being weird. I was not in HR. I was not in people operations. I just decided to go for it without asking for permission from anybody, or running it up the flagpole, only for it to die in committee of approvals. I didn’t ask HR, I didn’t ask legal, I didn’t ask comms. And then all of a sudden, I was writing emails that went to 56,000 people at Google. So it’s ’cause I played it hot. I just went for it, and I begged forgiveness, not permission. And there are so many smart, talented people sitting on brilliant ideas that never see the light of day, because they’re waiting for permission or waiting for perfection, quite frankly. And they don’t just start and put something out there like 10 bullets on a document, hoping that maybe two dozen people will come, and then it ends up being a lot bigger than that.

Brett McKay: All right, so being weird is about embracing your quirks, sharpening them into strengths, standing out in a good way. It’s all about leaning into what makes you unique. And then playing it hot is a stance towards life where you show up with your weirdness, with boldness, and energy instead of trying to play it cool and blend in. There’s risk with this though, with playing it hot, ’cause people could just think you’re weird in an off-putting way, or you might step on some toes. But the benefits will typically outweigh the risk.

Jenny Wood: Yeah, let me touch on that for a moment, ’cause this is critically important. When I was launching this book, Kim Scott was a big mentor of mine. She’s like, “Jenny, this is your time to beg.” This might fall a little bit more into the selfish or shameless trait, but she’s like, “This is your time to beg.” I had built relationships with a lot of authors and influencers, and I asked maybe 100 of them to help promote the book, whether it was sharing it on social media or on their blog or if I could be on their podcast, or it was actually probably closer to 200, or whether they’d write a newsletter about it. And there was one very, very famous author, and if I said the name, I will not for their privacy, but if I said the name, every single one of you would know it. And this person not only said no, but also ended our friendship and our mentorship relationship, and man, did it sting. I lost sleep over it. This was just a couple of days before a pub date, and it was a time when I needed to not be losing sleep, and it stung.

But if I had used that rejection as an indication to just start playing it cool and not asking for help or not being weird or not shamelessly putting myself out there, then this book would not have been nearly as successful as it has been. And so, even though the outcome wasn’t what I would have wanted, and it really felt like a punch in the gut, and it still hurts to this day, it still hurts to be told no from someone you deeply respect and admire because you’ve played it too hot. But it doesn’t mean that the decision was bad. It was just the outcome that wasn’t ideal. And so, I still carry that play it hot mentality with me because, 80% of the other people said, “Yes, we’d be thrilled to help.” And then 20% said no respectfully. And this was like the one outlier who said no, in a way that was painful for me. But it’s okay, because we push past those painful moments and we keep doing great things.

Brett McKay: Besides playing it hot, another way you suggest you can be more weird is sharpening elbows. What do you mean by that?

Jenny Wood: Yeah. Well, this is an example of when I was at Google, and the most senior leadership team, kind of the equivalent of the C-suite of this org of Google, was meeting in London to decide a reorg and the fates of the people below them. Now, the people below them, myself included, were not invited to London for the actual meetings. But lo and behold, a bunch of us showed up in London to rub elbows. It’s like call, sharpen our elbows to be in the same proximity, to have coffee chats, to be present. And again, if you wanna be invisible, you can, but it’s not going to help your career because being in the same room, if you’re not invited, if you don’t have a seat at the table, bring a folding chair, as they say. But I think just showing up makes a big difference. It’s like the classic line, 80% is just showing up. And it was astonishing who decided to fly to London and who decided to not and what the outcomes looked like. Because politics are real, relationships are real. And again, it goes back to the biggest lie you’ve been told in your career is just keep your head down, your work will speak for itself. It won’t.

Brett McKay: At the end of each chapter, you have a section of what you call trait traps. And this is how the quality you’re talking about in that section can turn into a weakness. And for the weirdness section, you say the trait trap there is when you start thinking of weirdness as being rude, annoying, just obnoxious. So the takeaway for weird is that you wanna be weird in a good way. Just by doing the things that other people aren’t doing, doing things that might be unusual or unusually bold, just standing out from the crowd. But it’s in a good way. You’re not being obnoxious about it. Let’s talk about another trait, and that is selfish. Nobody wants to be known as selfish, but let’s talk about this first. How can selflessness be harmful? I think that’s a good way to start this question.

Jenny Wood: Yeah. Well if you give everybody a leg up at your own expense, you’ll end up getting trampled. So start showing up for yourself. I redefined this as the courage to be your own champion. And even when I was running the, Own Your Career program, I feel like I took my eye off the ball on my core job a little bit, and I was almost over-delegating to the leaders who reported to me. And then, I had one conversation with my manager who was basically like, Jenny, get your eye back on the ball on your core job. And then it even meant that I had to kind of reshift some of the priorities to either peers who I delegated to or direct reports because I had to look out for myself. I needed to maintain a good performance course that I could continue bringing this good work to the world. And it’s tough. It’s tough, especially as a leader, to be selfish and say, my career matters too. But at the end of the day, I deeply believe that as much as your manager is supporting you and your career, they’re gonna put their career first.

And they should, because if we’re not showing up for ourselves, then who is? And for the parents out there, you might say, oh, well, if I were to ask you the question, who’s more important than you? Start showing up for yourself. And if you were to say, oh, my child is more important than I am, but does your child need a martyr who’s exhausted and depleted and hungry and sleep deprived? No, go to that yoga class, go to that golf, Sunday regular session that you do with your buddies, and take the time that you need so that you can replenish and show up for the people in your life in a thoughtful and intentional way.

Brett McKay: So being selfish actually allows you to serve better?

Jenny Wood: Yeah.

Brett McKay: Yeah. So what does positive selfishness look like for you?

Jenny Wood: Well, it’s saying yes to the big and no to the small, at least in a work context, but also in a life context. So what’s big? The Q2 strategy project that your C-suite really cares about. What’s big? Improving customer satisfaction by 12% quarter over quarter. Again, in a work context, what’s small? Being the 18th person to reply all on the happy birthday Jimmy email. Give him a high five when you see him at the water fountain. What’s small? Attending every single meeting where you neither add value nor derive value. And how often do we do that? And what’s small? Being the person who always takes notes in the meeting or always raises your hand to lead the wellbeing pillar. Like, yes, these things are good for community, for culture building. Yes, it’s nice to occasionally plan the company picnic for the summer. But if you did it the last several times, if you took notes the last several meetings, then those small actions constitute what I call nap work, not actually promotable. So avoid more than 10% nap work. Because no one ever gets promoted for being responsive to email. And yes, do a little bit of it.

But if you notice that you’re dialing up to 30%, 40%, and granted this stuff can be easy, it can be simple. Sometimes it avoids the big scary projects of the customer satisfaction increase. But if you do too much of it, it’s just not gonna serve you well. So I say don’t nap at the office because you wanna do the big work that moves the business, because what moves the business is what moves your career. And same thing in your life at home also. Like, what are the things that you need to respond to on a given day and what are the small things you can avoid? And maybe it is not responding to every text that comes in, right?

Brett McKay: Yeah, that nap work, I can see that can be a trap for people in their career. ‘Cause often nap work, it’s easy and it’s concrete and it’s actionable. It’s like, oh, I’m doing something. But if you look at it, it doesn’t really move the bottom line on things. And so, I can see it can put someone in a position where like, I just do so much for the company. No one appreciates what I do, but you’re doing stuff that, it’s nice, but it’s like not necessary.

Jenny Wood: Yeah it invites more work, but it doesn’t invite more responsibility.

Brett McKay: Yeah, so say yes to the big, no to the small. But a lot of people have a hard time saying no. Any advice for people who have a hard time saying no to that sort of rinky-dink stuff because it makes them feel bad?

Jenny Wood: Yeah, so two tools are the agenda avenger and the power postpone. ‘Cause nobody wants to say no, and then feel like a jerk. But there are so many ways you can say no and not feel like a jerk. In fact, I do have a freebie if people wanted it. It’s @itsjennywood.com/sayno. It’s eight scripts tools, tricks to say no to meetings, projects and favors, because we get them all the time and we feel guilty. We don’t have the wild courage to say no. And then sometimes a yes turns into like 20 other yeses. It’s like, can you do this quick thing? Okay, cool. Now can you schedule this thing as a result of it? Oh, we’ve got to reschedule it. Now we’ve got to inform this one person. So one little yes can turn into 20 different yeses. But you can use the agenda avenger, which is, let’s say for example, someone asks you to hop on a call. You could say, I’d love to get a better sense of what you wanna cover. Could you send a quick agenda first?

If you push back, and that’s why it’s the avenger, the agenda avenger. If you ask them for an agenda, they’re gonna have to think real hard if you really need to have that meeting. And by the time they put together that three, five point agenda, they might just realize that can be solved over email. How many times have we been in a meeting that really should have been an email? And then, another one is the power postpone. So I’m planning to take a sabbatical coming up here for six weeks. And so, that’s a natural power postpone where I say, I can’t meet now, but I can meet in about eight weeks. And then, sometimes it just resolves itself. Or if they really, really wanna have that meeting or have you on that project, then they can wait. But oftentimes, it just disappears. And those are two of the eight very practical tools I share with people to thoughtfully say no without feeling like a jerk.

Brett McKay: Yeah, the asking for an agenda, I’ve used that a lot in my career. So I’ll get people who will email me like, “Hey, I got this thing. I’d love to hop on the phone to talk about how we can partner together.” And it’s like, what does that mean? Okay. So I send an email like, hey, this sounds great. What are some concrete ideas you have right now on how we can partner? And then they’re like, oh, I don’t know. Okay, well, once you have some ideas, maybe we can hop on the phone then. But when their ask is kind of vague, it’s like, well okay, I’m gonna have you be a little more specific so we can figure out if there’s actually something here for us to do.

Jenny Wood: Yeah, definitely. Or another version of it is, I’d get tons of people who’d reach out to me and say, “Hey, my nephew would love a job at Google. [laughter] It’s always someone’s nephew would love a job at Google. Another strategy here is yes, if, or yes, when. Yes, we can do that if you put together three job recs that look interesting to you. Or yes, we can do this when you send me your idea of the perfect job or something like that. So again, it’s similar to the agenda avenger. You’re not specifically asking for an agenda, but you’re saying, yes, we can do it if you do this or when you do that. So yes, if, or yes, when, to also see if that meeting really needs to happen.

Brett McKay: Another tactic you have for being more selfish in a positive way is winn. W-I-N-N. What’s that?

Jenny Wood: I love this one. I’m so glad you’re bringing it up. So this is play to winn. What I need now, W-I-N-N, as you said. And this is about being selfish about how circumstances might change. And there’s this wonderful story about a session singer for Pink Floyd named Clare Torry. A session singer is someone who is hired for a very small fee to come in and sing backup vocals or something as part of a track for one individual song for a band. So in London, Clare Torry came in and she was paid 30 pounds to sing these backup vocals for the great gig in the sky on a Pink Floyd album. And so, she collected her 30 pound fee and went home and didn’t even know that the song had made the album until it came out. Well, it turns out that album went 14 times platinum. A little bit more than, and her vocals are legendary. If you know the song, it makes the song. And so, she played to win. She said, what I need now is to sue Pink Floyd and ask for a much significant part of the royalties and a songwriting credit.

And then she was really smart and selfish to do that. And Pink Floyd was smart to settle out of court for an undisclosed sum. So what might that look like for you? Maybe your company has just gone through a reorg or layoffs and you’re now doing the job of two people and you’re overworked and overwhelmed and feel like you’re underpaid. Well, what I need now might be giving yourself the advice that you might give to a friend, which is put together three slides, go to your manager, explain the work that you’re doing, ask for a new title, ask for a raise. And we selflessly say things like, oh, but I’m just happy to have a job. Or, what about Alan and Sarah and Louisa? They’re doing hard work too. What about their raises? Well, being selfish is standing up for yourself. And sometimes what I need now is the permission we need to recognize that it’s okay to ask for something when the circumstances have changed.

Brett McKay: Yeah companies or CEOs, they play to win.

Jenny Wood: Heck yeah, they do. And that’s why they’re so successful.

Brett McKay: Yeah, if they never think, well, we promised this guy this job for a long time. It’s like, well, okay, the situation now is like, we’re losing money and we have to make cuts to keep this company afloat. That’s the situation now. So we got to make the cuts, I’m sorry. It’s not personal or anything. They’re playing to win.

Jenny Wood: Yeah, one of my best managers, Mike, said to me in a one-on-one when I was really being a workaholic and not taking any vacation, he’s like, “Jenny, you are capped out on vacation. When is your next vacation gonna be? I’m worried you’re gonna burn out.” And I said, I know, Mike, I’m just so passionate about this project and this new team. And I just, I love Google so much. And he was like, I think about my saying this and like what a ridiculous, it’s not that, Google’s an amazing company. Don’t get me wrong, but what a funny thing to say to justify me not taking vacation. And I will never forget his retort back. He said, “Jenny, that is great. But I want you to remember that Google doesn’t love you back.” And just like you said, Brett, they’re gonna be selfish. Any organization is gonna be smartly selfish if there’s a financial crisis and they have to have a RIF, a reduction in force, if they need to shift priorities and take a big project away from you, if they need to freeze hiring, if they need to pause promotions or give lower raises or bonuses, they will be selfish left, right, and center.

So you can be selfish too, but there’s this power imbalance. Where we look to our companies or we think that our boss’s boss has so much authority and that we can’t ask for what we want, but the best leaders, the future leaders are the ones who ask for what they want because you’re displaying future leadership skills.

Brett McKay: Are there any trade traps with selfishness?

Jenny Wood: Yeah you want to, with all these traits, be expanding the pie and not re-dividing the pie. So I do advise people to look for ways that are mutually beneficial as opposed to, for example, when I needed to be a little bit more selfish about my career and kind of get my eye back on the ball, if I was going to insert myself more in a project that I delegated to a peer or a direct report, I would think about something else that they could do that would bolster their profile as well.

Brett McKay: We’re going to take a quick break for a word from our sponsors. And now back to the show. All right, let’s talk about shameless and shameless. This is all about leaning into your strengths and not being afraid of showcasing them. It’s all about having some swagger.

Jenny Wood: Yeah.

Brett McKay: What do you think holds people back from promoting themselves?

Jenny Wood: I think that this is the biggest challenge with Wild Courage. I do. I think that people feel insecure. They feel rife with imposter syndrome. They feel like they don’t deserve it as much as somebody else. They feel like they don’t have the skills that somebody else has. But there was a moment in a meeting that I was leading where there were maybe 20 people in the room and this guy came in and he’s like, “This is a shameless plug, but I put together this spreadsheet that might help you.” And he shared it over the group chat. The emojis go flying. The chat explodes. Oh my gosh, this is gonna be so helpful. This is gonna save me 20, 30 minutes every time I need to create this project proposal for clients. And yet he led with, this is a shameless plug. And it’s like, what’s the shame in that? You’re sharing something useful and helpful and a time saver for people. And yet we hesitate to share our wins. And I think one of the most helpful tactics here, is to make it consistent, make it a system. If, for example, you shared every Monday what I call a shameless Monday email with your boss with four bullets, two things you’re proud of that you did last week and two things you’re excited about for this coming week, that is so powerful.

First of all, it makes it a lot easier to put together your performance review at the end of the quarter and your accomplishment bullets. But it also just systematizes talking about your wins and it becomes more natural. It becomes more of an update. There’s huge positive externality of then they might CC their boss. Or if you’re a leader, you could share this with your team and CC your own boss. And then you’re sharing with your team your priorities, which people love to know what their boss is up to that day. So the shameless Monday email can be really effective as you lean into your strengths and not be afraid to showcase them.

Brett McKay: Yeah, that’s a powerful idea ’cause your boss has no clue what you’re doing. He might have a little bit of a clue, but he probably doesn’t know everything. So this just makes it more explicit.

Jenny Wood: Yeah, definitely.

Brett McKay: You also have the power portfolio. What’s that?

Jenny Wood: Oh, I love the power portfolio. So the power portfolio is made up of your power assets. And just like a financial portfolio, you wanna have a mix of soft skills and hard skills or of business skills and people skills like you’d wanna have a mix in your financial portfolio of stocks and bonds. So these are the three strengths you have or the three things that you bring to the table that can move the business forward. So I had a coachee named Martina and she came to me with three power assets. She said, “Mine are communication, organization, and supporting others on launches.” And these were okay, but they needed tweaking because again, we want a mix of business and people skills. So yes, people skills matter, but managers and leaders want to know what business problems you’ll solve, because that’s what their boss is grading them on. So that’s why you wanna diversify your power portfolio and aim for a mix here. So we tweaked it. So communication became executive communication. Organization became project and program management, which she was phenomenal at. And supporting others on launches became go-to-market strategy.

Again, same ideas, different word choice, higher impact, shameless, right? But it’s just being more powerful in your language. And again, like organization versus project and program management does have a very different je ne sais quoi. To me, organization sounds weak. It sounds feminine. Not that that’s a bad thing, but in the context of wanting to show your leadership skills and show more of the value you bring to the customer, project and program management just sounds a lot more powerful. And so, we strengthened them by doing that exercise. But even aside from your specific language choice, a lot of people, don’t know their strengths at all or their talents and can’t articulate them in a bit of an elevator pitch. Like some people might just draw a blank if I say, what are the three things that, often I will say execs draw a blank when I say, what are the three things you bring to your team? And they really have to think about it. So it requires writing down maybe 20 things that you think you are pretty good at, things you’d love to do as a child, things that you’ve helped move the business forward on in the past. It might require bringing them to a coach or a mentor or a boss and triangulating it with other people think, and then you can whittle it down to three.

Brett McKay: And I imagine after you whittle it down to the three, you need to figure out what are some things that, like concrete things I can show, that showcases that I have these traits, be able to show that to people. Hey, I’m great at this thing. Here’s what I’ve done.

Jenny Wood: Oh, absolutely. If you’re talking about these in a resume or again, an accomplishment bullet, preparing for a performance review or promotion, you want to use what I call ROI, not the classic ROI return on investment, though this does give you return on career investment. It’s role, objective, and impact. What was your role in this go-to-market strategy? What was the objective? You wanted to launch the product with 10 million users in the first year. And what was the impact? You exceeded that goal and launched it to 11 million users in the first year. And also double your numbers. In any context, double your numbers. Or even going back to… When I say double your numbers, I mean in that example, I used 10 million. Maybe you could say 10 million by day 90. Use physical numbers. It is so much more powerful. They don’t have to be fancy, like revenue growth percentage or actual dollars. It could be, I cut this email sequence down for onboarding new clients from five emails to three, making it more efficient. Or I’m 70% of the way through the fall athleisure line competitive analysis.

Even just saying, I’m 70%, or I cut this down from five emails to three, has a big impact on showing the concrete, the tangible value that you bring to the table. So double your numbers anywhere you can, whether it’s in your shameless Monday email or a resume or accomplishment bullets or your power portfolio when you’re talking about your strengths in the specific situations with ROI where you demonstrated these power assets.

Brett McKay: How are you being shameless with the promotion of this book you’re doing?

Jenny Wood: Well, a big part of promoting the book is having companies buy the book in bulk. So there are books that are sold one at a time, and there are books that are sold 500 at a time. Because this book is so much about, it’s about wild courage in all areas of life, but there’s a bias toward professional wild courage and really thriving within your company, within your organization, and not saying, hey, go quit your job and be a solopreneur, be an entrepreneur. It’s really helping you feel engaged, feel happy, feel successful, feel motivated within your organization, which companies should love and want to buy. So I think this has the potential to be the kind of book that people buy 500 at a time. So how am I being shameless? I recognize that opportunity, and I sent about 300 emails to leaders, friends, acquaintances, secondary connections, subject line, are you interested in buying 200 copies of Wild Courage? And then I put a bunch of details. I’d happy to do a 20-minute complimentary fireside chat if you did. And I sent the first 100, and Brett, I thought that by the end of the day, those checks would just be rolling in for those bulk purchases.

But as it turns out, the budget is not always there. The timing’s not always right. There was a lot of ghosting, a lot of rejection. So shameless in this context is having the courage to just keep going despite all of that rejection. And this was different than the rejection of the one person who cut off our friendship. This was rejection at scale because there were so many people. I probably didn’t hear back from 90% of the people in that first 100. So what did I do? I tweaked the offering. Rather than 200 copies in the subject line, I put 50 copies. Rather than overwhelming them with too much information about the details of how this partnership could work and me coming to do a fireside chat, I whittled it down to just a few sentences. So you can use that rejection and tweak, dial your shamelessness up and down to what might better appeal to the audience.

Brett McKay: Well, this kind of ties in nicely to one of the other traits of being reckless. Like you’ve been reckless with your being shameless.

Jenny Wood: Yeah.

Brett McKay: Let’s talk about that. What does healthy recklessness look like?

Jenny Wood: Well, it’s the courage to err on the side of action, because better to learn from your mistakes than waste time predicting the consequences of every decision. Think fast and fearless. And if you’re on the fence, do it. And for all of you overthinkers out there, for all of you pro-con list makers and like me, left-brain thinkers who are in a lot of analysis paralysis, just thinking about like, what’s the worst that could happen. Even leaving Google for me took a lot of recklessness. And it was hard for me to get to the point where I knew I wanted to leave. And that was a moment where I felt my eyes fluttering closed when I was driving my son back home from choir practice because I had just taken on too much. I had my day job. I was running the, Own Your Career program. There was all this external interest that was budding about my work, including this book. And I was also trying to be a wife and a mom. It’s like five roles. And I was exhausted. I was struggling with lowercase a anxiety. I was oftentimes up between 2:00 and 5:00 AM. And I just was totally sleep deprived and physically, emotionally, and mentally unwell.

And so, I reached the moment where I felt my eyes closing as I was driving Ari home from choir, that it was probably time to go. But it took me about 12 to 18 months to muster the courage to do it. And that’s ’cause I wasn’t reckless enough. And so, I think I was caught in truths and tales. Truths are facts. They’re verifiable facts. This microphone I’m speaking into is black. I’m holding a piece of paper in my hand. But tales are the stories we tell ourselves to make sense of the facts. And so, part of recklessness is separating the truths from the tales.

And so, I really struggled with that leaving Google. The tales I told myself were, I’m gonna have no identity if I leave Google. Another tale, what if we run out of money and have to move out of our house in Boulder by all the trails that I love so dearly? Another tale I told myself is my parents are gonna be disappointed in me because I’m the breadwinner for my family. But then, when I broke it down to actual truths in that situation, a truth would be, yes, I’m not gonna get a paycheck every other week with the Google logo on it.

A truth would be, I can find other ways to have a new identity. A truth would be, my parents have always supported me and are supportive of me leaving Google as well. So that helps you be reckless when you separate the truths and the tales and really break it down to fact versus fiction.

Brett McKay: So another thing you talk about in this reckless section is this react framework. What’s that and how can that help you overcome failures so you can maintain that bias towards action?

Jenny Wood: Yeah, well, sometimes failures are not big colossal, I lost the project or I lost the deal. Sometimes a failure is just a moment that happens that’s cringeworthy during the day. And we’ve all had those. And one of mine was when I sent an email intended for six people to, I think it was 23,000 people at the time. That’s how big Own Your Career was at the time. And I sent it instead of to the volunteers working on Own Your Career, I sent it to the entire Own Your Career alias. And Brett, this was an unintelligible email. It was just a subject line that was three sentences long with nothing in the body. And it was a testimonial of someone who had said they loved the Own Your Career program and that they’d gotten promoted as a result of it. And so, the subject line was just TT: Atkinson Me, which is the person’s name, but it’s a really unusual name. And then I had typos in the subject line. And this went to 23,000 people, including many in the Google C-suite. So I was mortified. I pressed send and then I slowly dragged the mouse to the unsend only to not get there in time.

And here’s what happened. So React is how I overcame that horrible moment of mini failure. It stands for recognize, empower, apologize, celebrate, and trust. Recognize that not everything you do will be perfect. E, empower yourself to own it quickly and clean it up. Take a deep breath. It happens to everyone. And so, I really just had to put on my big girl pants and say, I can clean it up. I can recover from this. Then I did. A is for apologize. I directly apologized to TT. She was not intending for her feedback about Own Your Career to get broadcast to 23,000 people. C is for celebrate. Celebrate the unexpected goodness that comes out of a mistake. I got hundreds of pings and emails back, and not a single one of them said, you jerk, I can’t believe you distracted me with this nonsensical subject line. No, everybody was checking in on me. Everybody wanted to take care of me. Everybody wanted to help me and empathize with me. And they all said things like, Jenny, I promise nobody cares about this, like you do. Nobody’s paying attention. Everybody understands this. It happens to everyone.

They were so empathetic. So that’s celebrating the unexpected goodness that comes out of a mistake. And that’s also the T is trusting that your fellow employees will have your back. And by the way, the other part of C, celebrate the unexpected goodness is, I wrote up this react framework. I then shared it with the whole Own Your Career alias and said, here’s how I recovered from this mistake. And it ended up being the most popular tip of all time that I had ever sent. So it just goes to show you that you can make lemonade out of any lemon. And that’s the react framework.

Brett McKay: All right. So reckless, just take more action, have a bias towards action, and you can overcome those little setbacks and failure. It’s not a big deal. It’s not gonna be a career ender for you. Another trait is being nosy. And I love this section. ‘Cause you start off that section talking about how your grandmother was nosy and how that probably saved her life during World War II. What happened there?

Jenny Wood: Yeah. So my grandmother was in hiding during the Holocaust in Budapest, Hungary. And she left to get a bucket of water for the other people in hiding with her. And she walked down the street and somebody from the Arrow Cross Party, which was sort of the Nazi equivalent ruling party in Hungary, rounded up her and some fellow Jews at gunpoint. And they marched them to a building and they had them against a wall. And my Bubbie, my grandmother, I called her Bubbie, knew that there was no getting out of this. She was doomed. The options were, basically she was gonna get marched onto a train and taken to Auschwitz, like so many other people had, or she was gonna have a summary execution and get shot right there against the wall. And there were literally dead bodies in the street when this was happening, as she told the story to me, in Hollindale, Florida at the age of 93, when we were recording her Holocaust survival stories. And her only option, she told me, was to get nosy. And so, she asked the soldier, this scared, terrified, timid soldier, a question.

And she asked, what would happen if I were to step out of line? And she wasn’t necessarily looking for the answer. She was looking for his reaction. And he answered with the Hungarian idiom, which I will translate to English, which equals, is the mademoiselle so stupid or just pretending to be? And it was a little bit of a jokey answer. She saw a lightness in his voice. He almost cracked a smile. And she really saw his nervousness. And it made her realize that she had a small window here to step out of line, because he didn’t yell at her. He didn’t hit her with the gun. He didn’t cock the gun. And so, just by being nosy, having the wild courage to ask a question, it was the only way she was able to survive that scrape. So she stepped out of line and started walking down the cobblestone street. And she said she remembered hearing the click of her heels every time she took a step as she just kind of slowly breathed in and breathed out and hoped that nothing would happen. And it didn’t. And she returned back to the attic safely. And so, she really only survived because of her nosiness, because she had the courage to ask a question.

Brett McKay: So this is all about asking questions, what it means to be nosy. Why do you think people have a hard time asking questions in their career?

Jenny Wood: We think it makes us look stupid or uneducated or unknowledgeable. Or think about how many times, for those of you who work in an organization that has a ton of acronyms. You think, oh, well, it’s too late. I’m already in this role for four months. I can’t ask that basic question. I can’t ask that simple question again. But nosy is the courage to get insatiably curious because curiosity drowns out fear and pulls you toward what is most exciting to you. So use it as a compass. And curiosity shows leadership, it shows ambition. It’s a great way to overcome nerves at a networking event rather than feeling like you have to impress somebody. Go ask them a bunch of what and how questions like, what was the most interesting session for you so far? Or how long have you been in the industry and what brought you here? Or how have your peers been responding to these sessions? Or how are you using AI right now? What and how questions are so powerful and they take the pressure off of you in any kind of new relationship or networking situation or a meeting with a mentor where you feel like you’ve got to be all buttoned up and prove yourself.

Just start asking and start listening. And even the best leaders, going back to the person who’s a few months into the role and they’re like, oh, I’m too far in to ask what that three letter acronym stands for. But the leaders who we admire most are the ones who have the confidence, the shamelessness, the boldness, the recklessness to say, “Hey, what does PRT stand for on this slide? I just wanna make sure that for everybody in the room who’s new, we redefine that.” And everyone sighs a sigh of relief that somebody finally, had the boldness to redefine that acronym of the thousands that are used at the company. And when it’s a leader who does that, I really admire it.

Brett McKay: You also talk about how you can use nosiness or asking questions to turn envy into a springboard to success. What does that look like?

Jenny Wood: Well, we’ve all got those people in our life who we’re jealous of. It could be a friend, it could be a colleague. And I say use envy as your engine and steal their blueprint. So, there was someone named Molly who I just deeply admired. She was a peer of mine. We were always competing for promotions and I always thought she was three times as good as I was. But instead of being jealous and having it create a scarcity mindset for me, I thought of it as an abundance mindset where I could learn from her. I could get deeply nosy and I could kind of discover her recipe for X, Y, Z skills. So she was really good at project management. And anytime we were launching a new program, she would have this awesome Gantt chart, which had all of the dates and the accomplishments that needed to happen over a six-month period of time. She was really good at communicating next steps. She was really good at delegating. She would bold the person’s name in each email and put a deadline for what needed to happen next. She would thank everybody and be very positive and empathetic.

And so, rather than just be jealous and say, oh, why am I not good at Molly? Like I resent her. I just went to her and I said, Molly, could I do three 20-minute sessions with you where you review some of these project management skills with me and I can basically steal your blueprint? And I would write down these things on an index card and I would put them by my desk and I would use her strategies. Or I did this with another manager, Ted, who was just such a phenomenal presenter and never said, um, in his presentations. And so, then I would gamify it for myself and I’d say, I’m gonna count how many times Ted uses um, in a 10-minute presentation, and I’m gonna try to beat it. So again, rather than being jealous, I used envy as my engine and I would steal their blueprint. And that is rooted in being nosy. It’s being curious versus jealous.

Brett McKay: This reminded me of Plutarch, the famous Roman biographer, philosopher guy. He talks about two types of emotions. There’s envy, where you see someone who’s better than you and you just feel bad and you wanna bring them down. And then he says, “The opposite of that is zeal.” It’s where you admire someone’s excellence and then you wanna imitate it.

Jenny Wood: I love that.

Brett McKay: So curiosity, being nosy can lead to zeal instead of envy.

Jenny Wood: I love that.

Brett McKay: I really like that.

Jenny Wood: I love that.

Brett McKay: Let’s talk about being manipulative. You had an instance where you used manipulation on a past AOM guest, and that’s Vanessa Van Edwards. She talks about charisma. How did you manipulate Vanessa into helping you achieve one of your goals?

Jenny Wood: Yeah, well, I really wanted to meet Vanessa. We haven’t talked about obsessed, but I’m obsessed. I wanna meet the best people. I wanna do the best work. I wanna help people in the most high-impact way. And I knew that part of that was building those relationships with authors so that I could partner with them around time of book launch, and also just learn from each other and enjoy each other’s friendship and mutual value exchange. So I was headed to Austin for some work meetings. Someone had just introduced Vanessa and me over email. And so I said, I’m gonna be in Austin Thursday through Sunday. I would love to take you out for coffee. And she said, “Oh, what are the chances? I’m actually gonna be out of town those exact dates for a keynote.” And so, I think a lot of people would just take no for an answer and be like, okay, another time. And of course, another time never comes. But I wanted to capitalize on this opportunity. So I said, what time does your flight depart on Thursday?

And she said, “It departs at 3:00 PM. Well, my flight was scheduled to get in later than that. But a quick little switcheroo flight change and $60 to Delta Airlines had me coming in before her flight so I could meet her. And I said, what are the chances I get in at 1 O’clock? And so, what if we met right by your gate for coffee? So, did I lie? Yeah, sure. Liar, liar, pants on fire. But I will stand behind that lie all day long that I wasn’t actually originally getting in at 1:00 PM. And maybe I even said I was getting in at 1:00 to just make sure it worked for her before I made the flight change. So I think I actually did lie about the time my flight landed before I made the change. But I tell you, $60 to meet Vanessa Van Edwards in person, it’s a bargain at twice the price. And so, we feel like everything has to be coincidental or just has to work out or fate. But man, I just believe that serendipity isn’t found, it’s made. And manipulative reclaimed is the courage to build influence through empathy and to build lasting relationships.

Because whether you’re selling a product, an idea, or yourself, the ability to end friends, allies, and supporters is all about mutual benefit. So figure out what people want and go get it for them. In fact, something happened this morning where I got an email from the person who ran the PR campaign for the book. And she said, actually, I got an email a couple weeks ago, but I totally forgot to respond to this. It said, hey, would you be willing to write a testimonial for me on LinkedIn? So I would call that nosy, right? That’s great. And then I forgot to respond because I’ve had a lot going on. And then she followed up. I’d call this bossy. She said, “Hey, I hate to nudge you, but I’d really appreciate this review on LinkedIn. Any chance you could do that?” And so, what I think would have made it even more powerful, is if she’d been manipulative and said, “And by the way, I’ve drafted a couple sentences for you that you can tweak as you see fit.”

Because when I talk about manipulative and how it’s all about finding mutual benefit and figuring out what people want and getting it for them, what I want is time back. So I love doing favors for people, but they take time. And so, had she been manipulative and said, “I’ve already written it for you.” That gives me what I want, which is time back and makes it a lot easier for me to say yes. So I did say yes, but now I have to do the work. And it’s still something I have to add to my to-do list. So that’s where manipulative can be such a good thing and win-win and expand the pie, whether you’re changing your flight to meet somebody because relationships should be high reward, but also high investment, or asking someone to do a quick favor for you, like my PR person did today.

Brett McKay: Yeah, so being manipulative, it’s all about just being influential. That’s what it’s all about. And your definition of just being influential is like, thinking win-win, finding out how you can get what you want and need, and while at the same time delivering what someone else needs and wants. It reminds me of this famous quote from Dwight Eisenhower about leadership. And he said, “Leadership is the art of getting someone else to do something you want done, because he wants to do it.”

Jenny Wood: Oh my gosh, that’s so beautiful.

Brett McKay: Manipulative, but that’s just leadership. That’s being influential.

Jenny Wood: Yeah.

Brett McKay: Yeah. So last one, you talked about obsessed. You’re obsessed with meeting Vanessa Van Edwards. That’s another one of your traits of wild courage. What does positive obsession look like?

Jenny Wood: Well, it’s pushing, persisting, performing, because frankly, none of these traits will serve you if you don’t learn to deliver, not for some company, but to achieve your own ambitions. So obsessed for me was, I wanted a job at Google in 2006. I was bright-eyed and bushy-tailed and I submitted my application online having no clue what the job was that I submitted it for. But I discovered there was maybe sort of possibly a formatting funkiness when I uploaded my resume. And whether there was or wasn’t, when I didn’t hear back from Google, I used that as an opportunity to print out that resume on a piece of paper and hop in my mom’s 10-year-old Honda stick shift and drive to the Google office and sit there on the couch until someone came out and talked to me. And I remember the receptionist, it was a shared office space, was like, no, it’s not really protocol for Googlers to come out and talk to you. You can drop the resume here. And just like firm as a tree rooted to the ground, with my smile kind of like, cheeks quivering as I kept that smile on.

I was professionally persistent and said, oh, it’s okay, I’ll wait. I really do need to talk to somebody because there was a problem with my resume. There’s this study that says, people defer to because. It was a study about people standing in line to make Xerox copies and someone from the back went to the front and said, “I need to go to the front of the line because I need to make copies.” Just because they said the word because, they were more likely to be let into the line, even though of course, everyone was there to make copies. But the research suggests that people defer to the word because X, Y, Z. So I said, because there was a problem with my resume, I need to speak to someone. And eventually someone named Elizabeth came out, and I talked a little bit about how I had just come back from working abroad and backpacking through South America, which I understood were very googly skills or things that people did to be kind of well-rounded and global citizens. And then, then and only then, did I hear back from Google once I showed up.

Actually, not even then. I didn’t hear back. I didn’t get her business card. And then I tried every single permutation and combination of first initial, last name, first name, last name, just last name @google.com. Her name was Elizabeth Kelleher. So I emailed E. Kelleher, Elizabeth Kelleher, Liz Kelleher, Elizabeth@google.com. And then finally, I found the right combination. And when I followed up, then I heard back. So that is my flavor of obsessed. And it’s okay to be obsessed. It’s okay to stick your neck out. It’s okay to show that you want something deeply, because people like enthusiasm. People like energy, people like positivity. And that’s what I was trying to show, because it didn’t work just submitting my application online. Silly protocols and rules are there to deter the deterrable. But I just decided I was gonna be undeterred. And I got the job. And here we are almost 20 years later.

Brett McKay: Yeah. You got to play it hot. Don’t play it cool.

Jenny Wood: Yes. Definitely.

Brett McKay: So we’ve talked about these different traits. Is there one you think that people would get the most benefit from working on or like the one that people struggle with the most that if they started working on today, they’d see a lot of ROI? .

Jenny Wood: I think shameless. I think there’s just a lot of change in the world right now, a lot of economic uncertainty, a lot of change with, the onset of AI, a lot of layoffs, a lot of reorgs, and that’s hard. There’s this moment where my husband and I were living with my grandmother on her pullout couch in Manhattan while we were job hunting. And John shared some unfortunate news. We sat down to dinner. He said, “I’ve been part of a major company restructure and I got laid off today.” Well, I’m crushed as a newlywed, but I look across the table at Grandma Lila, who was like, a total spitfire at four foot 10 and 90 pounds. She was not just shameless. She was unstoppable. And she said, “John, no is just an opening offer. Don’t sign the paperwork.” And John and I look at each other trying to silently communicate what we’re thinking. And then finally, John sighs and says, uh, I think a layoff is like a one-sided thing, Grandma. They say, you don’t work here anymore. And I say, okay. And that’s when Grandma Lila sighs and says, “Well, sure, it would be more comfortable to take no for an answer, but don’t let fear shape your decision, don’t let shame shape your decision. You both want something, right? They wanna get stuff done, even though they can’t afford to pay you. And you want a job because it’s easier to get a job when you have a job.”

So finally, John relents. And the next day he goes to his VP and he half-heartedly offers to stay on for 10% time and pay, while he job hunts. And shockingly, they accept. Now, I’m not sharing this as some influence tactic per se. The point is Grandma Lila’s lesson. Don’t let fear, don’t let shame shape your decisions. Get shameless.

Brett McKay: Yeah, and it worked out for your husband, ’cause he got some time off. He had a little money to live on, kept his benefits. And then a few months later after this crisis that this company was going through, he kind of abated. The company hired him back full time. And it was all because he’s willing to do something we think of as a bad thing, to be shameless. He had to be uncomfortable and ask for something that apparently wasn’t an option. Well, Jenny, this has been a great conversation. Where can people go to learn more about you and your work?

Jenny Wood: Well, the book’s available anywhere. Electronic, e-book, audiobook, hardcover, Amazon, anywhere books are sold. And then you can find me on itsjennywood.com. And I love helping organizations with keynotes. I love helping execs through one-on-one coaching. I do some small group coaching. And I would love to be in touch and help you find your wild courage wherever you are and whatever you are chasing.

Brett McKay: Fantastic. Well, Jenny Wood, thanks for your time. It’s been a pleasure.

Jenny Wood: Thank you so much, Brett.

Brett McKay: My guest today was Jenny Wood. She’s the author of the book, “Wild Courage” It’s available on amazon.com and bookstores everywhere. You can find more information about her work at her website, itsjennywood.com. Also check out our show notes at aom.is/wildcourage, where you can find links to resources and we delve deeper into this topic.

Well, that wraps up another edition of the AOM Podcast. Make sure to check out our website at artofmanliness.com where you can find our podcast archives, as well as thousands of articles that we’ve written over the years about pretty much anything you can think of. And if you haven’t done so already, I’d appreciate it if you’d take one minute to give us a review on the podcast or Spotify. It helps out a lot. And if you’ve done that already, thank you. Please consider sharing the show with a friend or family member who you think would get something out of it. As always, thank you for the continued support. Until next time, it’s Brett McKay. Reminding you not just to listen to the AOM Podcast, but put what you’ve heard into action.

This article was originally published on The Art of Manliness.

Years ago, we published articles on personal finance goals to strive for in your 20s and in your 30s.

Now that I’m in my 40s, I decided to revisit this series to see if I needed to update my financial goals in my first decade of midlife.

Your 40s are an interesting time, money-wise. Many men enter their peak earning years during this decade. Yet their expenses often increase significantly at the same time. High-school-aged kids may need cars, and those same teenagers may subsequently need help paying for college. Your parents are retiring and aging into their 70s, and you’re starting to think about what financial support they may require in the last decades of their lives. Meanwhile, your own retirement shifts from a distant abstraction into an approaching reality.  

During this decade where you’re both starting to enjoy the fruits of your labors, but feeling the pressure of additional demands, you want to make moves to ensure you’re on stable ground now and in the future.

Below are 10 goals, backed by research and the advice of personal finance experts, that will help you not just survive your 40s, but thrive in that decade and in the decades to come:

1. Consider Consulting a Financial Advisor

With higher income and more responsibilities, your financial life is more complex in your 40s.

So consider hiring a fee-only financial advisor to help you navigate these complexities. Fee-only financial advisors don’t make money from selling financial products like insurance or mutual funds, reducing conflicts of interest.

You can pay a fee-only financial advisor by the hour to get advice on planning for retirement, paying for college and potential weddings, updating your estate plan, and reviewing insurance.

If you’re looking for more comprehensive guidance, you can set up an arrangement where the financial advisor gets a percentage of the assets they manage for you.

You can find fee-only financial advisors in your area by searching https://www.napfa.org/.

2. Maintain a Robust Emergency Fund (6–12 Months of Expenses)

By now, you should have a solid emergency fund. In your 40s, the goal is to increase its balance to match the expenses you likely have as a middle-aged man.

Aim for at least six months of essential expenses, or up to a year if you’re in a volatile industry or single-income household. Job hunts for people in their 40s often take longer than for those who are younger. If you were to lose your income, a six-month cash reserve ensures you can keep paying the mortgage and feeding the family while you find your next role. It also prevents you from raiding retirement accounts or going into debt.

Keep this fund in a liquid, low-risk account. Don’t touch it unless it’s a true emergency; replenish it as soon as possible if used.

3. Maximize Your Income

For many men, their 40s are the highest-earning decade of life. The median annual salary for men usually peaks between 45 and 54. Make it a goal to leverage these years as much as possible to set yourself up for true financial security.

To make the most of this decade, you’ll want to maximize your income.

Raises won’t usually fall into your lap. You’ll need to ask for them proactively.

If your boss won’t budge on giving you a raise, consider switching roles or even companies. Changing jobs mid-career can often substantially increase your salary, but so can moving up the ranks at your current job; be sure to check out our podcast on getting a promotion for some solid advice on how to continue to work your way toward the literal or metaphorical corner office.

Additionally, look into creating extra income streams through side businesses or freelancing. At this stage in your career, you probably have valuable expertise others will pay for. Consider moonlighting as a consultant. The extra income you earn now could even evolve into part-time work after you retire.

It’s worth noting that your 40s are not only peak earning years, but may be the last years you have your kids at home. You don’t want to be so focused on maximizing your income that you miss out on maximizing the time you spend with them before becoming an empty nester. It’s a tough line to walk, but strive to strike a balance between filling up your financial treasury, and your memory bank.

4. Avoid Lifestyle Creep

It’s natural to want to reward yourself as your income rises — to finally get that dream car, upgrade to a bigger house, or take more vacations. And you should allow yourself to start splurging a little more in your 40s; you’ve earned it by grinding through your 30s.

But don’t go overboard; every dollar spent on upgrading your lifestyle is one less dollar available for debt reduction or savings. Remember, too, that the cost of another car or a bigger house isn’t just the initial purchase price, but what it will cost you in maintenance, insurance, etc.

Start enjoying yourself more in your 40s, while saving enough to ensure that the next four to five decades are enjoyable as well.

5. Double-Down on Retirement Savings (Aim for 3X Your Salary)

In your 40s, retirement is no longer the abstract-seeming thing it was in your 20s. It will potentially be a concrete reality for you in twenty or so years.

Experts suggest having about three times your annual salary saved by age 40. Don’t worry if you’re not there yet — many aren’t — but use that benchmark to motivate you.

In your 40s, strive to save at least 15% of your income (ideally 20% or more) for retirement. As you save for retirement, take full advantage of tax-advantaged accounts like 401(k)s and IRAs.

How should you allocate your retirement savings in your 40s? When I put this question to personal finance expert Nick Maggiulli, he suggested that for many, it might mean reducing risk due to the increased liabilities they likely have in midlife: “In your 40s and 50s, you should consider reducing this risk to fit your liability profile better. For example, you could consider going from an 80/20 stock/bond portfolio to a 70/30 (or something similar). The key here is not maximizing your net worth, but maximizing your chance of long-term survival.”

6. Eliminate Non-Mortgage Debt and Work Toward Being Mortgage-Free

Ideally, you’ll have paid off all non-mortgage debt in your 30s. If you haven’t, make that a priority in your 40s. Aggressively tackle any lingering debts, like car loans and student loans.

Once you’ve eliminated all non-mortgage debt, start focusing on your mortgage. While you don’t necessarily need to pay it off during your 40s, you should have a clear plan for eliminating it as soon as financially feasible.

If you can swing it, start making extra principal payments. Even one extra payment a year (or adding, say, $200 extra each month) can knock years off a 30-year loan. Check with your lender that extra payments go toward the principal.

7. Bolster Kids’ College Funds (But Not at the Expense of Retirement)

In your 40s, your children may be in high school, and college costs are looming. Ideally, you started a 529 account for your kids in your 30s; if not, start one now. With 529 accounts, gains and distributions/withdrawals for education aren’t taxed.

As you save for your kids’ education, don’t do so at the expense of your retirement. Your retirement should always be the priority when saving. Your kids have options for education financing, but you don’t have one for retirement.

8. Plan for Aging Parents and Family Care Responsibilities

More than half of 40-somethings are either raising children under 18 or financially supporting adult children, and have at least one parent aged 65 or older. About a quarter of adults in their 40s and 50s actively provide financial assistance or regular care to their aging parents — a percentage that only increases as members of this “sandwich generation” and their parents grow older.

Prepare for a future with aging parents by talking to Mom and Dad about their financial health. Do they have sufficient retirement savings, a will, power of attorney, or healthcare directives? Knowing this upfront can prevent surprises during a crisis.

Second, discuss future care preferences. When their health declines, would your parents prefer living with family or moving into an assisted living facility? Clarifying this sets expectations and shapes future plans. If you have siblings, hold a meeting to define roles and discuss shared costs.

Finally, consider preparing financially by creating a “parent fund” for predictable expenses like medical bills or housing.

Check out the book Mom and Dad, We Need to Talk: How to Have Essential Conversations With Your Parents About Their Finances. I thought it had a lot of good advice.

9. Do an Insurance Check-up

If you bought term life insurance in your 30s (as we recommended), revisit your coverage. Major changes — like more kids, a bigger mortgage, or a higher income — might require additional coverage. A common guideline is 10–15X your annual salary, ensuring your family could replace your income if needed. Term policies are still affordable in your 40s (though premiums rise), so lock in coverage until kids graduate college and your mortgage is paid off.

Also consider umbrella insurance to protect accumulated wealth from liability lawsuits, and disability insurance to replace your income if you can’t work.

10. Do an Estate Plan Check-Up

You should have started your estate planning in your 30s; in your 40s, it’s time to do a check-up.

• Revisit and update your will to reflect current realities, like new assets or guardians for your kids.
• Double-check beneficiary designations on retirement accounts, insurance, and investments; these override your will, so accuracy is crucial.
• Ensure you have durable powers of attorney (for financial decisions) and healthcare proxies, naming people you trust.
• Explore advanced strategies like trusts or charitable giving if your estate is sizable.
• Communicate with your spouse and estate executor about your plans and where key documents are stored.

11. Plan Your Next Chapter of Life

Having a clear retirement vision guides your financial choices today. Outline your ideal retirement. When will you retire? Where will you live? How will you spend your time? Cruising? Volunteering? Working part-time? Answers to these big-picture questions will shape how you save in your 40s.

Next, calculate your retirement “number.” Most aim for savings that generate 70–80% of pre-retirement income annually. Use retirement calculators or a financial planner to check your progress, adjusting your savings or expectations if needed.

Finally, prepare for potential healthcare costs. You might live into your 90s, so your savings could need to last over 30 years after you retire.

Your 40s are a busy and sometimes stressful decade, but with thoughtful planning and strategic actions, you can balance today’s demands with tomorrow’s dreams. Use these goals as your financial roadmap, and you’ll enter your 50s with confidence and clarity, knowing you’ve laid a strong foundation for the years ahead. I’ll see you in 10 years with an article on financial goals for that decade of life!

Listen to our podcast with Nick Maggiulli about the 6 levels of wealth and how to reach them:

This article was originally published on The Art of Manliness.