The 5 Habits of Eventual Millionaires

500 interviews in, Jaime Masters is about to beat Napoleon Hill

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“Your only limitation is the one which you set up in your own mind.”

That was one of Napoleon Hill’s 13 conclusions in Think and Grow Rich, a book he wrote after interviewing over 500 wealthy individuals over the course of 25 years.

Hill was sent on this journey by none other than business magnate Andrew Carnegie himself, who, after selling his near-monopoly steel company, the U.S. Steel Corporation, became the richest man in modern history.

Carnegie used his money — the equivalent of $374 billion today — to build no less than 2,500 Carnegie libraries around the world, and when Hill interviewed him in 1908, he pushed him to support his cause of education rather than pursue a law degree.

Hill agreed and, nearly 30 years later, published Think and Grow Rich, which remains one of the most popular books ever, even after another century has passed. Estimates range all the way from 15 to over 100 million copies sold.

Jaime Masters is the Napoleon Hill of our generation, and she’s on the cusp of beating his record. Since 2013, Jaime has interviewed almost 500 people with a personal net worth of over one million dollars, made from being in business. Her podcast is called Eventual Millionaire.

In a 2019 interview she gave on another podcast, Afford Anything with Paula Pant, Jaime outlined the most common patterns she’s seen among all the millionaires she’s interviewed. Surprisingly — or maybe not surprisingly at all — the traits Jaime talks about were just as relevant when Napoleon Hill set out on his quest over 100 years ago.

Here are the 5 habits of eventual millionaires.

1. They continuously move forward — no matter what

In late 2017, Danielle Morrill sold her failing company, Mattermark. The sale didn’t recoup the $18 million VCs had invested, and, after five years, Danielle and her husband moved from San Francisco to Denver to start over.

As she spreadsheeted her way through her finances, Danielle made a fascinating discovery: The stock she had received while working at another company, Twilio, had grown so much in value that she could live off the money for the rest of her life, given she’d make reasonable withdrawals.

Danielle was flabbergasted:

It was very disorienting to have my net worth climb from something I hadn’t worked on since 2012, while my current efforts were amounting to nothing in economic terms.

Most people don’t get rich the way they think they will — but if you stay focused on that goal, you’ll probably get rich eventually.

That’s the first and most important observation Jaime shares in her interview:

“It’s the commitment that actually matters, more than the how of how to get anywhere. As long as you keep moving forward continuously to whatever that [goal] is, and you keep correcting your course, you’ll get there, even if the vehicle changes. That was a big thing that came up over and over again.”

Even if your current effort is failing, your next one might be a success. What you did years ago can still bear fruits tomorrow.

Warren Buffett says: “Someone’s sitting in the shade today because someone planted a tree a long time ago.” If you keep planting trees, chances are, someday, you too will sit in the shade.

2. They know what their strengths are

I once listened to Managing Oneself by Peter Drucker. I’ll never forget how hard the following words hit me as they spooled off the speakers in my car:

A person can perform only from strength. One cannot build performance on weaknesses, let alone on something one cannot do at all.

Drucker said “most people think they know what they are good at,” but “they are usually wrong.” It is more common for people to know what they are bad at, but even then, “more people are wrong than right.”

Eventual millionaires buck this trend. They know themselves, and they know themselves well. They’re not necessarily better at identifying their strengths and weaknesses, but they are committed to doing it eventually — just like they’ll eventually get that first million.

“They leveled up on their strengths times a million and actually got other people to do the stuff that they didn’t like,” Jaime says. She’s seen two primary ways people develop the self-awareness needed to succeed.

The first is self-improvement. Visualization, meditation, reading books — whatever activity includes structured reflection will help.

The second is getting outside perspective. In her coaching, Jaime first assesses the business — but really, she mostly assesses the owner. If the owner is unhappy or unhealthy, the business rarely does well, she says.

“It’s hard to self-diagnose. Asking questions to your friends that really know you, when you can actually be really vulnerable, is a fun one.”

Paula’s comment captures the idea in a nutshell: “It’s hard to see the label when you’re in the jar.”

You can only perform from strength, so you must know yourself. You can reflect for yourself or enlist others to help, but over time, make an effort to understand what you’re good and bad at. This is the only way to succeed.

3. They take active actions over passive actions

When I first launched my blog, I spent days picking a Wordpress theme, designing my logo, hiring a designer to redo said logo, and changing the layout of the website. Guess what I didn’t do much of? Writing.

Designing your blog when you should be writing on it, doing your accounting when you should be selling product, updating your Upwork profile instead of finishing your gig — these are passive actions.

“Passive actions are the ones that don’t get you out of your comfort zone,” Jaime says. They’re things that need to be done eventually but usually not urgently — and definitely not by you.

Active actions, on the other hand, will move you closer towards your true goals — and there are usually just a select few of them. “Not only does it have to get you out of your comfort zone, it has to align with the end goal that you want,” Jaime explains.

For example, the only way to double your revenue is to do sales and marketing. If you’re not doing either, you’re stuck in passive-action land.

New, young, and first-time business owners are especially prone to this trap. Doing the real work is scary, but it’s the only thing that works. “You could be really efficient at passive actions and make zero money,” Jaime says.

But it happens to business veterans as well. This is Jaime’s first question to coaching clients: “What’s making you money right now? Can we double it?” It’s so simple, but in business as in life, we often miss the forest for the trees.

Eventual millionaires do the work that matters. They ruthlessly prioritize the few essential tasks that align with their goals and cut out everything else. They regularly make time to think about what these tasks are, and if they find themselves being busy without getting anywhere, they pause and reassess.

Don’t get lost in passive actions. Do what matters and soon, you too will matter to the people you seek to serve. Your income is only a reflection of how much.

4. They find out what people want

In the 90s, a drunk friend asked Craig Wolfe at a party: “How about rubber ducks that look like celebrities?” Three years later, CelebriDucks was doing $1 million in annual revenue.

“Nobody would have thought twice about it,” Craig says in his interview with Jaime. “But I thought ‘That’s different.’ I didn’t know if it could work, but it was different.”

Eventual millionaires don’t dismiss crazy ideas. They entertain them. They notice when their mind goes, “That’s different.” They tune in to this gut reaction — and then, they make it a reality on a small, affordable, relatively fail-safe scale.

In Craig’s case, he called the company that had the rights to a famous cartoon character, Betty Boop, and told them he wanted to create a licensed rubber duck for the figure. In typical “You’re crazy, but we’ll be nice” fashion, they told Craig to go ahead, never expecting him to return — but he did, and they actually liked the product. CelebriDucks was born. 20 years later, they sell over 200 different rubber ducks and still make millions every year.

Eventual millionaires are committed to finding out what people want — and they’re willing to fail until they know. Your business may not be an instant hit like CelebriDucks, but the only way to make it a hit eventually is to keep trying ideas until one takes off. Jaime agrees: “In all of those failures that they had, they got really good at finding out what people want and actually value.”

You can do a pre-sale for your online course. You can make a real sales page for a product that doesn’t exist yet. You can call others for help. You can make sample batches. No matter how you do it, “having an actual conversation with a real human that would be buying whatever the thing is that you’re selling is really important,” Jaime says.

Find out what people want, and then give it to them at scale. That’s how you become an eventual millionaire.

5. They believe they’ll figure it out — no matter what

There’s a great story from Neil deGrasse Tyson about two people applying for a job. The employer asks: “How high is the building across the street?”

The first person says: “Actually, I studied architecture, and we had to memorize the heights of all local buildings. The building is 153 feet high.”

Indeed, that is the correct answer.

The second person says: “I don’t know, but if you give me five minutes, I’ll figure it out.” The employer agrees, and the person steps outside into the sun. She takes a measuring tape and writes down both the height of her own shadow and the shadow of the building. The shadow of the building is about 25 times longer than the shadow of her reflection, and so based on her own height of six feet, the person estimates the building is about 150 feet tall.

“Who are you gonna hire?” Tyson asks. “I’m hiring the person who figured it out. Even though it took them longer. Even though their answer wasn’t as precise. I’m hiring that person — because that person knows how to use the mind in a way not previously engaged.”

Creativity is the most powerful force in the world — but in order to use it, we first have to believe in it. That’s why “let me figure it out” is one of the most empowering sentences you can say.

When Paula asks Jaime if there aren’t some people who fail despite continuously moving forward, Jaime declines. “The ‘no matter what’ is the biggest thing,” she says. “It really is mindset stuff. I know that sounds super cliché, but a lot of people, even in the same business model, don’t take the continuous forward motion, even though they think they are.”

Belief in oneself powers continuous forward motion. Without one, you can’t practice the other — and so eventual millionaires spend a lot of time making sure they believe in their cause, their actions, and themselves.

There are two parts to this: You need to be convinced what you’re doing is the right thing, both for yourself and others, but you also need to be humble about how that thing is going to come about.

Jaime’s guests say, “I’m just gonna figure it out as I go. I don’t know if anyone’s done this before, I don’t know if I can do it or not,” but then “they just do it.”

Just like the second person in Tyson’s example, eventual millionaires come to every situation as a blank slate, which allows them to find creative solutions whenever their minds are presented with a challenge.

Be humble, creative, and always have faith in yourself. Solve each problem as it unfolds, and, soon, you’ll return home with much more than just a new job.


Being a millionaire will not make you happy. Millionaires face many problems we all share: Finding love, being happy, and feeling engaged at work.

They have, however, solved their money problems — and that’s not a bad place to start. At the end of they day, eventual millionaires did only two things to get rich, Jaime says: “They worked hard, and they kept going.”

Many of them, however, also share the five following patterns:

  1. They continuously move forward — no matter what. They don’t know how they’ll get there, but they know they have to keep going.

  2. They know what their strengths are. They’re committed to knowing themselves through reflection and asking others.

  3. They take active actions over passive actions. They refuse to get bogged down by what doesn’t matter and prioritize the few key tasks that do.

  4. They find out what people want. They do so with small-scale trial-and-error, and they keep failing until they succeed.

  5. They believe they’ll figure things out — no matter what. They believe in themselves and their mission because they’re both humble and creative.

If Jaime could give us just one tip on how to start with our eventual million, this’d be it: “Do the one thing you know you should be doing but haven’t.”

We can’t ask him, but for some reason, I’m sure Napoleon Hill would agree.

-Nik

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