How You’ll Feel Reaching Various Millionaire Milestones ($1M-$20M)

To celebrate the launch of Millionaire Milestones: Simple Steps To Seven Figures, I want to share how you might feel and what you might do as you hit various levels of wealth. Perhaps by sharing, I'll motivate you to save and invest more aggressively. We'll start with reaching your first million, then move on to $5 million, $10 million, and $20 million.

I stop at $20 million because once you surpass that threshold, there's not much left you can spend money on to meaningfully improve your lifestyle. Beyond $20 million, building more wealth simply becomes a game, a personal challenge, or an exercise in greed.

As the Chinese philosopher Lao Tzu once said, “A journey of a thousand miles begins with a single step.” When it comes to building wealth, you must be intentional. Treat managing your finances with the same passion and precision you give to your favorite hobby.

Those who wing it will wake up a decade from now wondering where all their money went. But those who stay intentional—reviewing their finances regularly and investing in their financial education—will build lasting wealth. More importantly, they’ll unlock the freedom to live life boldly, on their own terms.

1. Reaching Your First Million: Relief, Validation, and a Sense of Real Possibility

When you hit your first million dollars, you’ll feel an overwhelming sense of relief first and foremost. You’ll think to yourself, “Finally, all those years of saving, investing, and grinding have actually amounted to something tangible.” It's a huge milestone you should be proud of.

It’s like crossing the finish line of a marathon where the prize isn’t just a medal, it’s the ability to breathe a little easier. You won’t necessarily feel rich, especially thanks to inflation, but you will feel validated. You’ll realize that as an employee, building wealth is not just for other people or institutions, it’s for you, too.

Your first million will also give you a huge psychological unlock. Suddenly, you’ll see possibilities everywhere. The fear of financial ruin won’t vanish, but it will shrink given you'll be able to generate $40,000 – $45,000 a year in passive income, risk-free at today's interest rates. You’ll start to imagine what life might look like if you really ramp things up.

Most importantly, the first million is where you internalize a crucial truth: the snowball gets bigger on its own. Saving that first $250,000, as I write in my book, might have felt like climbing Everest. But once you have $1 million compounding at 5%–10% a year, you're talking about $50,000–$100,000 a year in passive growth without lifting a finger.

You can aggressively play offense now, not just prevent defense. You can afford to take more risks, something I wish I did more of when I was younger.

Common Pitfalls Getting to $1 Million:

• Lifestyle creep: As income rises, spending rises even faster for the undisciplined.
• Investment FOMO: Chasing the next hot trend (and blowing your finances up) instead of sticking to a plan.
• Quitting too early: Giving up on saving or investing because the early gains seem too small.

2. Reaching The $5 Million Milestone: Confidence, Options, and a Taste of True Freedom

Once you reach the $5 million milestone, a quiet but profound confidence starts to settle in. You no longer have to calculate whether you can afford the organic blueberries at Whole Foods. A $7,000 unexpected home repair or even a $50,000 investment mistake that plummets 20% soon after no longer feels like a big deal.

You also start to realize you have options. A $5 million net worth can throw off $150,000–$300,000 a year in passive income, depending on how it’s invested. That’s enough to exceed the median American household’s entire pre-tax income of ~$80,000 without working another day in your life.

If you’ve been stuck in a soul-sucking job or run a business that gives you ulcers, $5 million lets you walk away. But of course, try and negotiate a severance package so you have an even greater financial cushion when you do. If you’ve been dreaming of living abroad, working part-time, or starting your own business, $5 million gives you the luxury of choice.

Unfortunately, you’ll still worry about your finances.What if the stock market crashes? What if rental income dries up? What if health care costs explode? But you will rationally make contingency plans if any of these things happen.

Overall, your anxiety will diminish because you know you have true staying power. In a previous Financial Samurai poll, $5 million was the ideal net worth to retire with, followed by $10 million. You are set for life if you remain vigilant with your finances.

Common Pitfalls Getting to $5 Million:

• Overleverage: Taking on too much debt or trading on margin thinking it’s a shortcut.
• Burnout: Pushing too hard at the expense of health, family, and happiness.
• Status signaling: Overspending on cars, homes, watches, and jewelry to “show” you’ve made it. It's interesting, but some of the most insecure people I've met are also those with net worths close to the $5 million mark.

Looking Back At Retiring With $3 Million In 2012

I left my banking job at age 34 with a net worth of approximately $3 million. Adjusted for a 4% compound annual growth rate, that’s about $5 million in today’s dollars.

At the time, $3 million felt like enough because I only had myself, and eventually, my wife to take care of. My investments were generating around $80,000 a year in passive and semi-passive income. Combined with a severance package and the support of my wife—who was 31 then and willing to work for another three years—I felt it was time to peace out.

Still, I was nervous and insecure about leaving my day job so young. Looking back, I probably should have worked for another three-to-five years to further solidify my finances. With $3 million, I was much more argumentative in the comments section too.

That said, everything has worked out because I found purpose. I found something I love to do that generates supplemental retirement income, and, more importantly, I became a father. In the end, retiring early gave me the flexibility to build a more meaningful and fulfilling life.

3. Reaching The $10 Million Milestone: Abundance, Status, and Subtle Shifts in Relationships

At the $10 million milestone, your world view may shift again. Scarcity thinking—the nagging belief that there’s never enough—starts to dissolve, but never truly goes away.

With $10 million, you'll feel an underlying abundance mindset take over:

• You can generously tip service workers without thinking twice.
• You can say yes to experiences you once would have passed up because of cost.
• You can invest in your health, relationships, and personal growth without financial hesitation.
• You can eat wagyu steaks and toro sashimi until you're sick of them both.
• Upgrading to Economy Plus or even first class is no problem
• People don't piss you off as much anymore
• Perhaps best of all, you can easily speak your mind and stand up for yourself without fear of financial ruin

Being A Multi-Millionaire Can Have Its Problems

At this level, status becomes more visible, whether you like it or not. People may treat you differently once they know—or sense—your wealth. Friends and family might ask you for favors, loans, or business investments. You’ll need to develop a thicker skin and clear boundaries.

With $10 million, you'll probably embrace Stealth Wealth like a secret agent trapped behind enemy lines. You didn’t spend all these years building your fortune just to get hit up for handouts, judged, or peppered with investment pitches every time you leave the house or turn on your laptop.

As a millionaire ten times over, people will be quicker to judge your actions and far less sympathetic when you're feeling down. Even though millionaires have feelings and need love too, people may simply not care if you're feeling down and out. Hence, you purposefully become more guarded with your friends and acquaintances.

Thankfully, some of your relationships will deepen. You'll naturally gravitate toward people who genuinely don't care about your money.

No longer will you feel the need to maintain relationships just because someone holds sway over your financial or career future. Instead, you'll start surrounding yourself only with people you truly enjoy being around. Say goodbye to toxic relationships!

Having A $10 Million Net Worth And Children

If you have children, reaching $10 million also changes how you think about legacy. How do you empower your kids without spoiling them? How do you prepare them for a world where they don’t have to struggle financially the way you did?

Fat FIRE parents might worry even more because they no longer have traditional day jobs that force them into the office 40+ hours a week. At least if you have a day job and a $10 million net worth, your children will know that you are working hard. As a result, FIRE parents will likely have to make up a “trust fund job” to demonstrate their work ethic and purpose to their kids. Otherwise, they might ruin their perspective on life and money.

At the same time, with so much wealth, you may naturally start toying with the idea of making your kids millionaires too. You know firsthand how hard it was to get here, so it’s only natural to look for ways to help them shortcut the journey.

Just be careful. Taking away your children’s drive to become financially independent could end up being one of the greatest disservices you do for them. As you know, one of the greatest feelings is achieving something mostly on your own.

Common Pitfalls Getting to $10 Million:

• Neglecting tax efficiency: At higher wealth levels, minimizing taxes becomes just as important as investing well.
• Poor estate planning: Without smart legal structures, you risk losing millions to taxes or probate.
• Not cashing out or diversifying into safer assets: Outsized income and company valuations do not last forever. Without diversification, your net worth swings can be huge.

4. Reaching The $20 Million Milestone: Peace, Purpose, and a Reduction In Material Desires

Crossing into $20 million territory feels less like a major “event” and more like an arrival. You realize there’s almost nothing left to buy that will materially improve your happiness.

A $50,000 watch won’t make you feel better than a $500 one, so you don't get one. A $200,000 car won’t make you happier than a $50,000 one, so you drive your current car until it breaks. You could buy a third or fourth home, but would you even have time to enjoy them? You can't because you can only live in one place at a time.

The only real splurges you can enjoy with a $20+ million net worth are flying private, renting vacation homes for $50,000+ a month, and paying for $60,000+/year private grade school without worry. You could do these things with “only” a $10 million net worth too without, but you'll feel the expenses more acutely.

But even with $20 million, will you really be willing to spend $120,000 on a roundtrip private jet flight from San Francisco to Honolulu when four first-class seats cost just $10,000? Probably not. The more disciplined you are with your personal finances, the less likely you’ll be to splurge on such unnecessary luxuries.

You might also finally feel like you’ve won the lottery, as you could easily generate $1 million a year in almost risk-free income for the rest of your life. The happiest people with this type of outsized wealth recognize their luck and never forget it.

You start thinking about legacy in a more profound way:

At the $20 million milestone, the real luxury becomes time, health, and relationships.

• How can I make an impact beyond myself?
• Who can I help with this abundance?
• What institutions or causes will outlive me?
• Will my children grow up to be outstanding citizens who make something of themselves?

Ironically, at $20 million, if you’re not careful, you risk losing your edge. The hunger that fueled you to work harder, save more, and invest smarter might start to fade. That’s why having a purpose beyond money becomes so crucial.

In addition, once money is no longer a problem, all your other problems come into sharper focus. Neglected your spouse and children on your path to multi-millionaire status? That regret may now feel overwhelming as you can't get that time back. Prioritized your career at the expense of your health? Suddenly, nothing seems more important than getting fit so you can live longer now that you've won the lottery.

If you ever reach this level of wealth, never voluntarily reveal how much you have. Let others guess, but never confirm. Instead, throw them off the scent by looking and acting as normal as possible. Your health, happiness, and safety depend on staying humble and low-key. If you must share something, let it be your generosity.

Your Financial Worry Might Actually Rebound

Ironically, reaching higher levels of wealth can bring back financial anxiety. The more you have, the more there is to lose. A 20% decline could erase $4 million to $16 million. It's a gut-wrenching amount, even if you're still financially secure. That’s why your mindset naturally shifts toward capital preservation, all while trying to stay ahead of inflation.

One reason real estate and private investments become more appealing is that you don’t see the daily price swings like you do with public stocks. With your money locked up for 5 to 10 years, you're less exposed to the emotional rollercoaster of market volatility. As a result, you are more likely to feel at ease.

At this stage, the real battles are psychological. You may find yourself wrestling with how you should feel about having outsized wealth. Guilt is an emotion that sometimes emerges as you wonder why you? In time, you might even downplay your financial success, convincing yourself you’re not as rich—or as lucky—as you truly are.

Common Pitfalls Getting to $20 Million:

• Losing your drive: Without new goals, it's easy to plateau since nobody needs more than $20 million.
• Isolation: Wealth can unintentionally distance you from old friends and even family. Stay grounded, unless you proactively seek out friends who also have a similar level of wealth.
• Might get trapped in a bubble: Your expectations for how to spend, earn, and think about money can run completely counter to the 99.5% of the American population who have less.

Wealth Is Built on Thousands of Micro-Decisions

Each millionaire milestone you reach brings a sense of satisfaction. But it’s the $3 million, $5 million, $10 million, and $20 million marks that tend to feel the most significant.

None of these feelings—relief, confidence, abundance, joy, or peace—happen by accident. They happen because you took thousands of intentional steps over years, sometimes decades.

Remember:

• Every $100 you invest instead of spend
• Every hour you spend learning and creating instead of mindlessly consuming
• Every risk you take to level up your skills or career

It all adds up.

Time To Focus

Building wealth is a straightforward formula, but sticking with it takes resilience. Inflation will keep shifting the targets, and today’s milestones may look modest in thirty years.

But with enough discipline, patience, and purpose, you can achieve more than you ever imagined. The real reward is not just reaching a number, but growing through the process—learning, adapting, and gaining the confidence that comes from doing the work.

If you want to create a life of freedom for yourself and your children, take the first step today. You may find that the journey itself becomes the greatest part of all.

Pick Up A Copy Of Millionaire Milestones Today

As I wrote in Millionaire Milestones: Simple Steps To Seven Figures, “If the direction is correct, sooner or later you will get there.” Make sure you have the right resources to point you in the right direction.

Good luck on your financial journey. If you want to become a millionaire or multi-millionaire, my book will help you get there. You can pick up a copy on Amazon, Barnes & Noble, Books A Million, Bookshop.org, or anywhere you like to purchase books.

For those of you who’ve reached these millionaire milestones, how did you feel after hitting each one? Which financial milestone had the most lasting impact on your lifestyle and happiness? I’d love to hear your story—what changed for you, and what did you do differently afterward?

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How You'll Feel Reaching Various Millionaire Milestones ($1-$20M) is a Financial Samurai original post. All rights reserved. How you’ll feel and act after reaching each financial milestone will vary. But now you know what’s possible.