To celebrate the launch of my new USA TODAY national best seller, 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.
What Happened To The $3 Million Net Worth Milestone?
Some readers have asked why I skip the $3 million milestone, given the jump from $1 million to $5 million is large. I agree it’s a notable step.
Hitting $3 million is a solid financial feat—it can free you from a bad job or open new doors—but it doesn’t feel much different from $1-$2 million. I chose to highlight $5 million because that’s when the sense of freedom and financial security starts to feel exciting again, much like hitting your first million.
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.
Here's a fun clip from one of my favorite TV shows, Succession, which pokes fun at how $5 million is barely enough if you live in an expensive city like New York. You may not feel rich with $5 million in NYC, SF, LA, Seattle, or Boston, but you should feel comfortable enough.
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 inflation 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. Now I’m not.
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 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, 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.
If you're looking to diversify your real estate investments and generate more passive income, check out Fundrise, my preferred private real estate and venture capital platform. Fundrise manages around $3 billion in assets for over 380,000 investors. I've personally invested over $300,000 in their commercial real estate and venture capital offerings. They've also been a long-time sponsor of Financial Samurai.
At this stage, the real battles are psychological. You may find yourself wrestling with how you should feel about having outsized wealth. How dare you feel sad or ungrateful, but you sometimes do. 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.
The Next Million Dollar Windfall: Investing In AI
One of the ways I plan to make another million dollars is by investing in private AI companies. Since private companies are staying private for longer, more of the gains are accruing to early, private investors. It only makes sense to allocate more capital to this space.
I believe artificial intelligence will significantly disrupt the labor market in the future, potentially making it harder for my kids to find fulfilling careers. To hedge against this possibility, I’m investing in both private and public AI companies. That way, if AI does end up reshaping the job landscape over the next 20 years, our AI investments could perform exceptionally well.
Check out Fundrise Venture, an open-ended product accessible to all. It invests in the following five sectors:
- Artificial Intelligence & Machine Learning
- Modern Data Infrastructure
- Development Operations (DevOps)
- Financial Technology (FinTech)
- Real Estate & Property Technology (PropTech)
Roughly 85% of Fundrise Venture is invested in artificial intelligence in some capacity. In 20 years, I don't want my kids wondering why I didn't invest in AI or work in AI!
The investment minimum is also only $10, making it accessible and easy to dollar-cost average in. Most venture capital funds have a $250,000+ minimum. You can see what Fundrise is holding before deciding to invest and how much. Traditional venture capital funds require capital commitment first and then hope the general partners will find great investments.
I've invested $153,000 in Fundrise venture so far, and plan to keep investing until I build a $250,000 position to hopefully make another $1+ million return within 10 years. There are obviously no guaranteed returns when it comes to risk assets, so invest according to your risk tolerance and goals. Fundrise is a long-time sponsor of Financial Samurai. Our investment philosophies are aligned.
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, which has the best sale. The book is a top new release on Amazon and a USA Today National Best Seller.
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?
Special Promotion For 1X1 Consultation
For those interested in a more personalized experience: If you order 55 hard copies (available at a bulk discount), you’ll receive a 1-on-1 video consultation with me, plus a full box of books to gift to friends, family, or colleagues. This package is a 41% discount off my normal consulting rate. If you’re interested, please fill out the form at the bottom of my consulting page here and I'll get back to you within 24 hours with details.
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How You'll Feel Reaching Various Millionaire Milestones ($1-$20M) is a Financial Samurai original post. All rights reserved.
Sam,
for purpose of discussion above, would you include home equity or 401k/ira accounts that either can’t generate income or inaccessible until later in life.
Absolutely for net worth calculations.
Hi Sam, Do you think in 15 years 20MM investable with no debt will still be a lot of money? Also, with this nest egg can someone still fly private and have a 2nd home?
Sure, it’ll still be a lot of money. If inflation runs at 3% a year for 15 years, the purchasing power of $20 million falls to about $12.9 million. Still pretty good. Is that what you are shooting for, $20 million? If so, how much do you have now and how old are you?
I’m 41 and currently have around 8.5MM investable no debt. I would like to retire at 55. You think 20MM is reasonable by 55?
I think so. 14 years is a lot of time to compound.
How much do you think i could spend a year starting at 55 and never touch my principal?
Depends on the composition of your net worth. Check out my personal finance consulting page (https://www.financialsamurai.com/career-personal-finance/ ) if you want to get into a deeper discussion and analysis. I’m doing a promotion now to celebrate the launch of Millionaire Milestones (https://www.financialsamurai.com/millionaire-milestones-book/).
How about 30MM in 15 years? What is the purchasing power?
Very nice article Sam. Thanks
I am perhaps the poorest out here with barely 300k networth at age of 36 and about to loose my decent paying cybersecurity job but my only two dreams in life are one to achieve FIRE and two to create a company thats creates immense value to the world and become really big within next 7 years.
I had a poor childhood so I over realize the importance of money and never tend to overspend it. That said , i also realize the three tenets of life(Wealth , heath,Relation) needs to be balanced and money is not essential for happiness so i want to Atleast retire from job before 41 and work for self fulfillment and hapiness rather than money .
Hi Sam – first time commenter, long time reader. Wanted to say a big thank you. Coincidentally this post has aligned with our household hitting the $1M NW mark with us in our mid-30s. Granted it’s spread across different asset classes but your writing inspired me to save aggressively in order to get us here and has me motivated to go well beyond. I remember reading your writing back in 2012 and feeling like something unlocked in my head. Along the way I’ve been called cheap or worse by friends/people who spend everything and drive much nicer cars and live in bigger houses. But I’m feeling incredibly proud to be here, just as you described above, and your writing has me motivated to achieve even greater freedom. Thanks and keep up the great work – all the best to you and your family
Hi Scott – thank you so much for taking the time to comment and share your story. Huge congratulations on hitting the $1M net worth milestone in your mid-30s—that’s an incredible achievement and a reflection of your discipline and long-term vision.
I’m honored to have played a small role in your journey since 2012. It’s never easy going against the grain, especially when others don’t understand the delayed gratification mindset. But you’ve clearly proven the power of consistency, intentional living, and smart financial decisions.
Keep going! you’re building a powerful foundation for even more freedom and options in life. I have no doubt you’ll continue to surpass your goals. Wishing you and your family all the best, and thanks again for reading and sticking with me all these years! – Sam
P.S. I hope you pick up a copy of Millionaire Milestones. It will motivate and guide you to take action to make many more millions after that!
I don’t usually talk about investing outside of a very small circle in real life, but we had an interesting discussion last night. The topic was “when are you going to sell?”
Without even thinking, I blurted out “never.. it always goes up!”
Then the conversation shifted to “what amount is enough?” Are we just treating investing like a never-ending game, constantly chasing a higher and higher score?
It really made me reflect on why I was aiming for a specific net worth. That first million felt incredible because most of it came from what I saved. Delayed gratification. Discipline. And a lot of luck.
But now, most of the growth is driven by the market. I’ve contributed far less compared to the returns and while it’s great, it just feels more like a game than a meaningful goal.
I’m not exactly sure where I’m going with this, but I want to rethink what the magic number is and reassess it every year or so. Even though 2012 was 13 years ago, I think $3 million is still a good target.
The magic number is a moving target, which is part of the reason why it’s so hard to quit the money. $3 million is definitely a fantastic target to shoot for, especially if you wan to feel like a real millionaire.
Gotta love the stock market rebound going on right now!
Well said, Sam. I’ve just reached milestone #2, and you captured my thoughts perfectly. I definitely feel that I have options now. Even though I still have an extremely demanding job, I feel more free and relaxed knowing that I don’t have to continue if I don’t want to. However, I still get nervous about market downturns. Additionally, the dollar’s weakness has really hurt me since most of my investments are USD-based, but ultimately, I will need to exchange my dollars for Euros. Ideally, I would like to build a bit more of a cushion before retiring, as part-time work is not an option in my line of work. However, milestone #3 seems to be too far.
Finished reading Millionaire Milestones a few days ago. Highly recommend it for anyone inspired by this post!
I forget who said it originally, but “making my first million was the hardest” comes to mind. I completely agree for the reasons you laid out. To get to $1MM, you need to establish sound habits. Cementing a new habit for any pursuit, money, diet, exercise, etc. is not easy.
Once you hit $1MM, that likely means your habits are locked in. You just have to keep doing the same thing to get to $5MM and $10MM. You’ve already done the hardest part. You just need time.
Matt
I’m 59 and hit the $5 mark a couple of years ago when I sold my IT business to PE. I expect another liquidity event in abut 2 years through the equity I hold in the company that bought mine. I’m seriously ready to retire by the the end of the year – facing some burnout issues. We’re currently looking at legacy planning and purchasing 3 rental homes that we’ll eventually gift to our adult children. Just started reading Millionaire Milestones! Will be fun to hit the $10 stretch goal especially with no W2 income. lol
Right on Todd! Huge congratulations on hitting the $5 million mark and successfully selling your IT business—that’s no small feat! Sounds like you’re in a fantastic position heading into this next chapter, especially with another potential liquidity event on the horizon. Burnout is real, especially after years of grinding, so I totally get the urge to step back and enjoy the fruits of your labor.
Love the legacy planning strategy with the rental homes—such a smart way to build generational wealth while still maintaining flexibility and control. I’m honored you’re reading Millionaire Milestones and I hope it gives you some added motivation (and maybe a few laughs) on the path to $10M. Hitting that goal without a W-2 would be be fantastic. Enjoy the ride!
The funny thing is, with a several good years in the markets and economy, you could get to $10 million before you know it. The compounding effect is real and incredible once you have that nut!
When you’re done with the book, if you don’t mind leaving a review on Amazon or wherever you picked it up, I’d appreciate it. Every review counts and means a lot. Thanks, Sam
I will definitely provide a positive review once I’m done reading the the book (I already know it’ll be great!). I’ve followed FS for several years now and consider you a mentor (despite that fact that I’m older than you… lol!) a friend just recommended a podcast entitled “Founders” which I find utterly fascinating. Just listened to episode #384 called, “Ken Griffin: Founder of Citadel and Citadel Securities”. The story about Griffen is interesting to be sure, but the insight and lessons sprinkled into the podcast by David Senra are profound and absolutely golden. This will be required listening for my entire family as we embark on the next phase of growth.
To wait until a net worth of $10M to generously tip service workers is having an extreme scarcity mindset.
Thanks for sharing your sentiment. Yes, if you’re only tipping generously after reaching $10+ million, that may be concerning. But clearly plenty of people tip well before that net worth milestone too.
It also depends on what “generously” means. What does it mean to you?
To some, tipping 25% – 30% is generous, while to others, only tipping 50%+ is generous.
You may enjoy these relevant posts:
Keep Your Donation Amounts A Secret
The Importance Of Stealth Wealth For Happiness And Survival
A Tipping Guide To Counteract Tipflation And Feel Great Again
You never want to share your true income, wealth, or amounts of giving because you will always be judged. And often times, the people who judge you will have less or give less.
We can’t help but judge how other people spend their money. It’s just the human condition. The sooner folks can adopt a low-key, stealth attitude, the better.
I do 25% as the baseline tip for even just average service. 50%-100% would be the generous amount based on certain persons or circumstances. I started doing a lot more of it after crossing 1M several years back. At 10M, I’d probably go around tipping 50% each and every time! LOL
Sounds good to me! Thanks for sharing.
In the tipping article I wrote there are some people who just find tipping to be completely foreign into them. And it really is foreign in many cultures in Asia and Europe to not tip. So to each their own, I say!
Tipping culture in America is completely out of control. 25% for average service?
In Portugal, we offered a $5 euro tip (on an $85 bill) and in a discussion with our server, he kindly turned it down and explained that he appreciated the gesture but says he hopes the American tipping culture never comes to Portugal.
Mike what u dont understand is that servers in the U.S. make 100% of their income from tips. Their hourly pay is literally 2.15/hr and goes all 2 taxes. This is not true in Europe as laws are different.
This is just excellent! You nailed all the feelings with welcome words of caution. Thanks again!
$1M is a nice start. $3M…most people can retire happily. $5M….you can retire a couple of decades early. From personal experience.
Only in the midwest. That aint enough in SF, NYC, or Hawaii.
This is cringe worthy to read. At $10 mil you suggest upgrading to economy plus? LMAO. My net worth is less than $10k and I fly business only. Once I have $100k I’ll quit my job and never look back. Moving somewhere to south east Asia where I can live off $1000 a month comfortably. All I need is to generate 1% return a month and I’ll be sorted.
Love it! You’re clearly playing chess while the rest of us are stuck on checkers.
Business class with less than $10K net worth is some real big baller energy—I salute you. And if you can consistently generate 1% a month, forget retiring in Southeast Asia… you should be running your own hedge fund out of Bali with coconut wi-fi and a staff of ex-Wall St. interns.
I see First Class in your near future.
Great read on the different levels. Just short of Level 2 and totally living the burnout lifestyle, working too much for the money to reach higher levels. It has definitely affected my health and relationships. It is definitely a regret that I have looking back but looking to parachute out in the coming months. Will take a break and enjoy some time working health, family, and friendships.
Not really worried about finances as I grew up poor and know I will not go back to that.
Hi Chris – Thanks for sharing. I wish you good luck in your next chapter. Focusing on your health is a must!
I was burned out and suffering from chronic back pain, sciatica, and TMJ before I decided to engineer my layoff. Within 6 months, ALL my chronic pain went away. Even my white hairs stopped sprouting out. They haven’t come back 13 years later. Our bodies are telling us things. We should listen.
I don’t regret walking away from the money for my improved health AT ALL. Neither will you if you’re at $4+ million.
Check out: The Health Benefits Of Early Retirement Are Priceless
BTW, if you don’t mind leaving a review on Amazon, I’d appreciate it. Thanks!
I am getting close to #4 but I am already thinking about what to do with this abundance. I only have 1 child and I am afraid that wealth abundance will cause more harm than good, so I constantly think how to best use my wealth and the returns it will provide to provide a good life for him. I consulted with Fidelity about managing a portfolio even after I am gone so a portion of the dividends are distributed as a match to income generated by him. But I am still wondering about capital appreciation and how to handle that in the long term, as in when my child reaches his elder years. I have looked into this on the web but I can’t find any examples yet I find inspiring. I will give to my preferred charities from my annual returns as well, but the dilemma remains in what to do with the accumulated appreciation in the end.
I am in my early 50’s and milestones at this point are just numbers as I have everything I have ever wanted, plus the fact that I am the type that will NEVER fly first class out of principle because I am and will forever be stuck with a scarcity mentality. I do plan to maximize my positive life experiences in general and continue to work on how my work will benefit the causes I am most interested in after I am gone.
Early 50’s so similar situation as you are here. If a material portion is in retirement accounts, required minimum distributions will force you to decide. Is that planning the dilemma?
Also grew up with a scarcity mindset, so it is tough for me to spend money but know all this work and investing can’t be just for accumulating, right?
Chris, you sound like me. grew up with older parents that lived during the later part of the great depression. They saved all they could and never like debt. Now at 54 years of age with a net worth of 2 million and no debt, I have to retrain myself. One of the best advice is ” at some point you need to create a spending plan” I find its easier to spend money for others than on myself. I have become better spending and will keep working at it.
Sam,
Just finished your book. It is a great guide for financial success and thank you for putting it together. It is especially relevant reading for young people. I am giving it to my 25 yr old daughter and we will talk about it. For us, we are between 3 and 4. We retired a couple years ago and have been travelling 6-8 months a year as travel has been our passion for 20+ years. I am still struggling with the psychology/anxiety of not having enough money to last through retirement. It sounds stupid to even write this but the little nagging still rears its head more than it should. Even with the recent downturn our NW increased over 7 figures in the rolling 12 mo. period. I just don’t know how to turn it off. Thanks for the book and letting me vent a little.
Yes I get that same feeling even though I’m above Level 3… that has made me continue working longer than I probably needed to. Now definitely thinking about retirement. I’m 60 this year.
GB –
I STRONGLY recommend retiring. ;)
You never now how your health will hold up, or what world conditions might be if or when you want to travel to various places around the globe.
I never spent a minute worrying about getting cancer. Then at age 50, I was diagnosed with triple negative breast cancer. Suddenly, my goal in life was to survive the five years until I was eligible to collect my employer’s “Magic 75” early retirement ay age 55. At my time of diagnosis, the 5 year survivability rate was ~40%. I certainly did NOT like those odds! But I did make it to age 55 and took my 5 year period certain pension payout (which was a nice chunk of change). Plus, I’m still here 17 years later. :)
Post my retirement, we focused on fulfilling our travel dreams. Oh, I forgot to mention my husband retired a month before turning 50 due to having a heart attack about three months after turning 48. Neither of us ever spent a moment worrying about having a cardiac arrest, I can tell you that!
We were making good progress on our travel, when the COVID-19 pandemic pretty much shut the world down. Due to our ages and underlying health conditions, we held off traveling again until 2024.
You just never know what’s around the bend. So from my perspective, the earlier retirement, the better!
Wow—thank you so much for sharing your story. What a powerful and moving reminder that life really is unpredictable, and our time is never guaranteed. I’m so glad to hear you made it through such a tough diagnosis and that you’ve had 17 more years (and counting!) to enjoy life on your terms. That’s inspiring on so many levels.
Your point about health and world events disrupting even the best-laid plans really hits home. It’s easy to assume we’ll always have time “later,” but your experience shows just how precious now really is. Retiring earlier to reclaim time and freedom seems less like a luxury and more like a necessity—if we’re in a position to do it.
Thank you again for the heartfelt perspective. Wishing you and your husband continued health and many more adventures ahead!
Hi Jeff,
Thank you so much for reading Millionaire Milestones—I’m glad you found it valuable, especially as a resource to share with your daughter. That means a lot to me.
It sounds like you and your partner have designed a truly rich retirement, traveling the world and enjoying the fruits of decades of hard work. That’s inspiring, and exactly the type of life I hope more people can achieve through sound financial planning.
As for the lingering anxiety about money—believe me, you’re not alone. It’s not stupid at all to feel that way. Many financially independent folks still wrestle with the “enough” question, especially after spending a lifetime in accumulation mode. The worry often isn’t about numbers—it’s about peace of mind.
Sometimes it helps to create a clear plan for decumulation, simulate various scenarios, or simply give yourself permission to enjoy what you’ve built. You’ve already proven your discipline and foresight—now it’s about shifting into a mindset that allows you to fully appreciate it.
I’m honored the book could play a small part in your journey. And thank you for taking the time to share your story—it’s encouraging and relatable for many.
Warm regards,
Sam
Great article and spot on. I feel you may need a section for 3 million though. The gap between 1 million and 5 million is large. Having a 3 million section would be great.
I just finished the book! It was awesome. Highly motivating to save more, and invest more, and they’ll decide business. Thank you!
I hope everybody reads Millionaire Milestones. It’s like a modern-day version of the Millionaire Next Door, but so much better and more pertinent in today’s times.
Just hit one of these milestones. Went ahead and bought your book to show my appreciation for your insight. We are definitely out here reading and processing your material. Thank you.
Great article Sam, very relevant topic that resonates loudly. I recently crossed level 3 and am finding a very frustrating aspect, namely that we have enough to keep our current lifestyle going through retirement, but ultimately will end up with much more than we would like at the end. However, if we try to elevate our lifestyle (mainly through purchasing a second home) we end up introducing financial risk back into our lives, which seems to negate the main benefit of reaching this level. So I’m struggling mightily with the choice between remaining free of financial risk, but missing out on the benefits of elevating our lives and leaving too much unspent at the end, and elevating our lives but at the cost of introducing some financial stress/risk. Let’s just say I relate in a big way to cousin Greg from Succession! The clip you posted is my favorite scene from the entire show
Thanks for the thoughtful comment and for sharing where you are in your financial journey—congrats on reaching Level 3! That’s no small feat.
I completely hear you on the frustration. It’s one of the trickiest stages: you’ve built enough to feel secure, yet the idea of spending more to enjoy life (like buying a second home or upgrading your existing) brings back the very financial stress you worked hard to eliminate.
This paradox is something I’ve wrestled with personally and have written about in posts like The Fear of Running Out of Money In Retirement Is Overblown and How To Overcome The Guilt Of Spending Money In Early Retirement.
You might also find Income And NetWorth Necessary To Buy A Home At Different Price Points to be helpful with your decision as well. I came up with the guidelines to specifically address finding the right balance between enjoying our wealth and minimizing risk.
Ultimately, finding a balanced path—maybe renting a vacation home first or earmarking a “fun fund” annually—could help you enjoy life more now without tipping the scales back toward stress.
To replace Succession, if you haven’t watched Industry on HBO, it’s pretty darn good!
I faced a similar situation. I chose not to do the second home. Instead of a huge item like a second home that is hard to swallow (And hard to pivot away from) without significant impact to current finances I decided to elevate alot of other things which improved lifestyle and are not “permanent” – such as flying fist class, travel more and more luxuriously, added family/sunroom and upgraded bathrooms in primary home, etc.
Almost to the 4M net worth mark and I still get excited about every round number milestone. I’ve been through enough ups and downs in my 30+ years of investing to shake off any doom and gloom during market pullbacks and instead get excited knowing that my biweekly 457 plan contributions will be buying at a discount.
I’ve hit quite a few major plateaus/pullbacks after hitting milestones:
1M for first time 5/14/2015 (age 43) then not hitting new highs until 4/2016.
2M for first time 1/17/2020 (age 48), peaking at 2.03M on Valentines day before a little event known as Covid-19.
Took a gut punch down to 1.7M before enjoying the ride to 2.9M on 12/31/2021 (age 50).
After another drop, didn’t return to that level until 5/2023, finally hitting 3M on 6/16/2023 (age 51), and then on to my (so-far) high of 3.93M on 1/24/2025 (age 53).
1.5 years until my wife and I retire and we’re staying fully invested, since we’ll be able to ride out market fluctuations with our pensions.
Based on my experiences, being at 3M or 5M at that point seem to be equally likely!
For any younger readers who read this far – trust the process, don’t fear market drops when you’re young, and once you hit your goals, please pay it forward by helping the next generation match your success.
As a long term investor, I am between level 1 and 2. I am now at the point where I should stop saving and learn how to start spending. I am trying to engage in some lifestyle creep, I now ride in the front of the airplane, and get a larger cabin when I travel on a cruise ship, but it isn’t easy. I keep telling my wife “If we don’t spend the money while we are alive, our son will spend it when we are dead”.
Lifestyle creep gets a bad rap, but intentional lifestyle enhancement is well deserved after years of discipline. Flying up front and booking a larger cabin are quality-of-life upgrades, not wasteful splurges. Gotta get a cabin with a deck!
Enjoy it!
A real estate investor named Grant Cardone said in 2023 that “single digit millionaires are the new middle-class”. That’s quite a provocative statement given the vast major of Americans, let alone the world, aren’t even close to that (if we ignore primary home value). Having made it there, I do feel a relief, a quietude in the sense that I’m not worried about making ends meet or worrying about some major incident wiping me out.
And in sympathy to what you stated, kudos to my best bud, Jerome Powell, who’s prime rate dictates has helped met to generate significant income in the past few years, via CD ladders and other safe investments. And am disciplined and slightly frugal on the other side of the ledger.
Being over 70, my goal is simply to keep my asset balance stable or slightly improving year to year as I notch one less year of time left to live.
Appreciate your perspective—and congratulations on reaching a level of financial peace that many strive for but few attain.
Jerome Powell’s rate hikes have definitely been a gift to disciplined savers these past few years. Sounds like you’ve struck a great balance between capital preservation and enjoying the fruits of your labor.
Keeping your assets stable while embracing the time you have left is a powerful and grounded goal. Thanks for sharing! I hope you enjoy your wealth to the fullest in your 70s!
“As income rises, spending rises even faster for the undisciplined.” You are quoting Brown’s Law here, although he put it “Expenditures rise to meet increased income.” Brown was a fellow grad student of mine who made big money compared to us (2x what the rest of us made). When this was pointed out, his response was the above.
I’ve never heard of Brown’s Law, but thanks for sharing. Can we make it Sam’s Law from now on? :)
I’ll take your advice and not voluntarily disclose my net worth, but I have been fortunate in business and investing. I think you’re spot on with your assessment of the first two milestones. With the last two, I mostly agree, but believe there is a lot more variability. I especially resonate with the loss of drive, legacy concerns, and thoughts about my children’s finances. My only question is how much these have to do with money, and how much is a function of age?
There is nothing left to buy that will make me happy. But is this due to money enlightenment or just years of accumulation? I’ve already had nice cars, which didn’t make me happy (and actually caused some stress). I already have nice watches (I’m currently wearing a stainless Rolex Daytona I purchased 17 years ago). I like them, but I don’t need any more. I’ve lost some of my drive over the past few years, working less and turning down business opportunities, but I don’t know if this is due to my net worth or the fact that I’m about to turn 50 and I’ve been working hard for the past 30 years.
The same thought process goes for my legacy and my children’s finances. If I had the same net worth at age 30, I’m not sure I would have the same concerns.
Some of the other items you mentioned have a lot to do with personal choice. My three kids attend private school, but would even if my net worth were lower because it’s a priority for my wife and I. Conversely, I can’t ever see us flying private. While I usually fly business class when I’m alone, we fly coach as a family. We also don’t spend as lavishly as you suggested on vacations. These decisions were made to keep our kids financially grounded, and haven’t changed as our net worth has grown.
These net-worth milestones are a good mental model, but how we react to them also encompasses our age, how and when we made our money, and our upbringing and financial education. Thanks for an interesting article, as always.
Really appreciate this thoughtful reflection. You’re absolutely right—so much of how we react to wealth depends on our age, our upbringing, and the path we took to get there. I love your question about whether the loss of drive or desire stems from financial abundance or simply decades of effort and maturity. Probably a blend of both.
It’s refreshing to hear how intentional you and your wife are about grounding your kids despite financial success. That kind of discipline and clarity of values is rarer than most think.
Thanks again for adding such nuance to the conversation—your perspective helps sharpen the mental model.
I’ve recently crossed the $20M+ line after a liquidity event, and one “problem” I’m facing is how to give away money. I’ve always given a few thousand dollars annually to charity, but am more uncertain how to give away hundreds of thousands. For example, should I be taking a more active role in the causes I support? Should I give anonymously, or get the perks that come with being a big donor, such as being invited to private events?
Congrats! Was it an IPO or did you sell your company?
I found the best way to give away money is to volunteer your time at the place. You’re considering giving money to. Get to know the people who work at the organization and see and meet the people who are the organization is helping.
When you do, giving becomes easier as it feels more impactful. I’ve got to do more myself!
I got to commend you for thinking about this. You may consider starting a foundation, or working with a foundation, that aligns with your goals. Or joining a board to direct how the funds are designated.