The other evening, I went to a school reception held for parents and alumni who donated at least a certain amount in the calendar school year. It was a warm, intimate gathering where I mingled with other parents, shared stories, and listened to the head of school and a couple of trustees talk about the importance of giving. The event was not only a thoughtful way to acknowledge contributors but also a chance to learn about new school initiatives.

As I stood there, I realized just how powerful the act of giving is. When you give, you become part of something bigger than yourself. You contribute to the collective well-being of a community. You see tangible evidence of your support in the smiling faces of children, in the opportunities created, and in the positive changes made possible.

Giving Feels Better Than Receiving

One of the main reasons Financial Samurai has remained free since its inception in July 2009 is because it feels incredible to help others solve their financial problems.

Over the past 16 years, I’ve received thousands of messages from readers who’ve built more wealth than they thought possible, found the courage to negotiate better jobs, or even retired early to pursue their passions. That, in itself, has been the greatest reward for me, far greater than any subscription fee or paywall could have provided.

But here’s the rub: when your household consists of dual unemployed parents, donating any significant amount of money can feel daunting. As I listened to the head of school thank the donors, I couldn’t help but wonder: can my wife and I really afford to donate another significant amount to the school next year?

Since our wealth isn’t unlimited, we also want to set aside a similar donation for the Pomeroy Rehabilitation Center, which supports individuals with injuries and disabilities. At the same time, we’re still about $30,000 a year short of reaching our ultimate passive income number.

The Delicate Balance Of Remaining Unemployed And Giving

When you are unemployed or FIRE, every dollar you give slightly increases your chances of having to go back to work or running out of money before you die. Giving while unemployed is, in many ways, an act of faith: faith that your investments will hold steady, faith that your expenses won’t balloon, and faith that your calculations about your safe withdrawal rate are correct.

Add in the responsibility of raising children in an uncertain world—especially one being reshaped by artificial intelligence—and the decision to give becomes even more complex. It’s not just about you anymore. It’s about ensuring your children have opportunities and will be safe.

We spend endless time debating safe withdrawal rates and the 4% Rule in personal finance circles. So when you give, that money really should come out of your withdrawal rate budget. If you’re nearing your safe limit yet still want to give, the prudent move is to trim your spending elsewhere. Otherwise, your generosity could come at the cost of your financial freedom.

And yet, even with all these considerations, the act of giving still calls to us. Why? Because the returns on giving—emotional, psychological, even spiritual—are often greater than anything you could get in the stock market.

Solutions To Giving When Unemployed

If you’re unemployed or FIRE, here are four solutions that can help you still give.

1) Replace your expenses

Because my wife and I donated X amount in 2025, we agreed to cut back on other expenses by the same amount. The easiest area to slash was travel. Renting a vacation home in Hawaii for five weeks would have cost us $16,000–$26,000, depending on size and location. Instead, we stayed with family, my parents for four weeks and my aunt’s beach home for one week, and saved the difference.

That savings went straight into remodeling my parents’ in-law unit. Was it the same as sipping mai tais on the lanai of a $26,000 rental? Not even close. But it still felt meaningful. By redirecting money we would have spent on lifestyle luxuries, we were able to both give to the school and help improve my parents’ property.

2) Earn side income to give away

If cash flow is tight, create income streams specifically earmarked for giving. I did a stint in a fintech startup but quickly realized it wasn’t for me. Afterward, I turned to personal finance consulting, helping individuals with one-on-one sessions. These not only promoted my book, Millionaire Milestones, but also generated extra income that I could donate.

Even a modest side hustle can fund meaningful donations. For someone who’s FIRE, this is an empowering way to stay engaged, sharpen skills, and still make a difference. My wife also contributes by donating her time at our children’s school, a reminder that giving isn’t always about money.

3) Donate appreciated investments

A tax-savvy way to give is by donating appreciated stock through a Donor-Advised Fund. You avoid capital gains taxes while the organization receives the full market value.

For example, suppose you bought Amazon stock for $10,000 a decade ago and it’s now worth $50,000. If you sold it, you’d owe over $13,000 in taxes if you live in California, leaving just $36,800 to donate. By donating the shares directly, the full $50,000 goes to the nonprofit, and you also receive a tax deduction. That’s a win-win.

This method is particularly attractive when you’re living off your portfolio. It allows you to be generous without putting additional strain on your withdrawal rate.

4) Donate your time

Finally, when money feels too tight, don’t discount the value of your time. In fact, time is often the most precious resource you can give. Volunteering at your child’s school, mentoring young professionals, or lending your expertise to a nonprofit board can create ripple effects far larger than a check ever could.

My wife is Girl Scouts troop leader at our school and is volunteering in various other ways as well. I see the greater purpose and joy she has by being more involved. She also gets to interact more with the teachers and school administrators.

I’ve noticed that the times I’ve felt most connected to my community weren’t necessarily when I wrote a donation check, but when I was physically present—meeting people, sharing knowledge, and helping solve problems in real time. Money supports causes. Time transforms them.

Practice The Mindset Of Giving

One downside of FIRE is that it can make you overly cautious and stingy. You’re so conditioned to preserve your nest egg that generosity feels risky.

If you feel you can only live off $30,000 a year and ride a bicycle, then there’s certainly not much room in your budget to give. But ironically, giving often multiplies your returns in ways you can’t predict.

Not only does it feel fulfilling, but it can also open doors you never saw coming—new friendships, opportunities, even investments.

A friend of mine once met a venture capitalist at a charity function. That connection led to an early-stage investment in Anthropic, which 12X’d in value in less than two years. Sure, that’s luck. But it’s luck that wouldn’t have happened without showing up, giving, and engaging.

The truth is, you never know who you might inspire—or who might one day lend a hand to you or your children. Maybe one of you readers will become a bigwig 15 years from now, and if my kids are ever struggling to find work, you’ll remember the value you got from Financial Samurai and give them a chance. That would be amazing.

You just never know.

The Ripple Effect Of Generosity

At the end of the day, the exact dollar amount doesn’t matter. What matters most is participation. Giving is a practice, just like investing. You may never feel like you have “enough,” but if you can find a way to give—even a little—you’ll almost always end up richer in spirit.

Generosity is also contagious. When others see you give, they’re inspired to give too. At the event, I learned some parents contributed multiple times more than we did. I felt awe at both their generosity and their good fortune. Their example reminded me that giving is a spectrum, and we all have a role to play.

Financial independence gives us freedom. But true wealth comes from using that freedom to help others. You don’t need to be a billionaire philanthropist to make a difference. You just have to show up, contribute what you can, and keep practicing the habit of generosity.

And that’s exactly what I plan to do—with both money and time—for the rest of my life.

Readers, what are your thoughts on continuing to donate money while unemployed or FIRE? Is it irresponsible if you already feel on edge financially, or is giving still worth prioritizing? How do you personally find ways to keep giving when your active income dries up or becomes minimal?

Subscribe To Financial Samurai 

Pick up a copy of my USA TODAY national bestseller, Millionaire Milestones: Simple Steps to Seven Figures. I’ve distilled over 30 years of financial experience to help you build more wealth than 94% of the population—and break free sooner.

Listen and subscribe to The Financial Samurai podcast on Apple or Spotify. I interview experts in their respective fields and discuss some of the most interesting topics on this site. Your shares, ratings, and reviews are appreciated.

To expedite your journey to financial freedom, join over 60,000 others and subscribe to the free Financial Samurai newsletter. You can also get my posts in your e-mail inbox as soon as they come out by signing up here. Financial Samurai is among the largest independently-owned personal finance websites, established in 2009. Everything is written based on firsthand experience and expertise.

Embattled Federal Reserve Governor Lisa Cook is facing accusations of mortgage fraud—specifically, owner-occupancy mortgage fraud. The claim is that she took out two mortgages in two states, within two weeks, while designating both properties as her “primary residence.”

If true, it’s a terrible look for someone sitting on the Fed, the very institution tasked with upholding the rules and integrity of our banking system. It’s like the referee secretly betting on the game. That said, we’re all presumed innocent until proven guilty. It’s hard to believe someone so high up in the banking system, with so many eyes on them, would knowingly commit fraud. But stranger things have happened.

Since this site is all about saving, making, and investing more money to achieve financial freedom, let’s use this latest controversy as a springboard to better understand mortgages. After all, most of us rely on them to buy our dream homes. And the lower the interest rate, the more wealth we get to keep.

The Penalty For Mortgage Fraud Can Be Severe

The penalties for owner-occupancy fraud, which falls under the broader umbrella of mortgage fraud, can be surprisingly harsh, even if enforcement is rare. Technically, mortgage fraud is a federal crime under 18 U.S.C. § 1344 (bank fraud), punishable by up to 30 years in prison and fines of up to $1 million. In practice, though, the maximum sentences are typically reserved for large-scale fraud rings, shady brokers, or lenders gaming the system.

Still, lenders have the right to call the loan due immediately through an acceleration clause, which would require the borrower to pay off the entire balance at once or risk foreclosure. They could also retroactively re-price the loan as an investment property mortgage, meaning higher rates and fees, and cut off access to favorable refinancing or future loans.

Beyond the financial hit, the reputational damage can be severe. While the average borrower probably flies under the radar, public figures, brokers, and real estate professionals risk having their credibility torched if they’re caught. That may be what Lisa Cook is dealing with now.

But here’s the reality: owner-occupancy fraud is likely far more common than regulators would admit. The financial incentives are obvious, enforcement is weak, and the dirty little secret is that plenty of borrowers have quietly bent the rules to save money on their mortgages.

The Benefit Of Claiming Two Primary Residences For A Mortgage

The main reason why someone would claim a rental property or vacation property is their primary residence is because lenders offer lower mortgage rates for primary residence borrowers. Whether you are refinancing your mortgage or buying a new property with a mortgage, the average mortgage rate is usually around 50 basis points (0.5%) lower for a primary residence than for an investment property or vacation property mortgage.

On a million dollar mortgage, that amounts to $5,000 a year in interest savings. Over a period of 10 years, if the principal balance remained the same due to an interest only mortgage, that’s $50,000.

To the lender’s credit, since the 2009 global financial crisis, they have been making mortgage applicants go through the wringer to prove their income, wealth, and credit-worthiness. Lenders have been far stricter since 2009, and don’t want to be left with huge losses again. It would often take me two or three months to get a new mortgage.

Lenders will make you sign a document stating you are refinancing or taking out a new mortgage for a primary residence. You’ll also have to share a utility bill perhaps, but that’s easy to keep in your name.

However, not once, in my more than 15 mortgage applications, has the mortgage officer ever personally come out to verify that I was taking out a primary residence mortgage. And even if they did, how could they prove I wasn’t if I showed up to my empty or not empty rental property? They can’t, unless they hire a private deceptive to watch my every move for months.

Clearly, the mortgage industry doesn’t have the resources—or the incentive—to crack down hard on owner-occupancy fraud. Loan officers are focused on earning their commissions, while banks are eager to book profits and move on to the next borrower.

Why Primary Residence Mortgages Are Cheaper

From a borrower’s perspective, paying a 0.5% premium for a vacation home or rental property mortgage feels unnecessary. If you’re wealthy—or reckless—enough to buy a vacation property you only use a few weeks a year, you clearly have cash flow. Why should the bank tack on a higher rate?

And with an investment property, you’ve got both your income and rental income from a tenant to cover the loan. Shouldn’t that make the mortgage rate the same, or even lower, than a primary residence loan? You’re less risky given you earn rental income.

Unfortunately, borrower logic isn’t lender logic.

• Vacation homes: From the bank’s point of view, these are luxuries, not necessities. When the economy sours, vacation properties are the first to hit foreclosure—as we saw in the 2008–2009 financial crisis. People ditch the lake house before their main roof over their heads. Banks hate holding foreclosed properties, so they pad rates to protect against losses. Foreclosing on and selling off a primary home is easier because the pool of buyers is larger.
• Rental properties: Lenders assume you need tenant income to afford the mortgage. But turnover, vacancies, and late payments make rental income unstable. That’s why banks typically discount reported rental income by ~30% when calculating what you can borrow. What looks like bonus cash to you looks like unreliable income to them.

Meanwhile, a steady W-2 paycheck used to qualify for a primary residence is considered much safer. That’s why primary residence loans get the best pricing.

In short, banks view second homes and rentals as “wants” rather than “needs,” which makes them riskier, and riskier loans always come with a higher price.

The Legal Workaround to Getting a Primary Residence Rate on a Rental

The cleanest way to get a primary residence mortgage rate on a rental property is simple: follow the law. Take out or refinance the loan as a primary residence, then actually live in the property for at least one year. After that, you’re free to rent it out, and you’ll still be enjoying the cheaper rate.

This is one of the big advantages of the U.S. mortgage system. You can lock in a low fixed rate for decades. For instance:

• A 10/1 ARM gives you 10 years of fixed payments. Live there for one year, then rent it out while keeping nine more years at the primary residence rate.
• A 30-year fixed works the same way—live there for a year, then rent it out with 29 years of cheaper debt still in place.

This dovetails with one of my favorite real estate wealth-building strategies: buy a primary residence, live in it for two years, then either sell tax-free (up to $250,000 in gains if single, $500,000 if married) or keep it as a rental. Do this a few times over your life and you can comfortably build 3–6 properties that fund retirement—all while staying 100% compliant with the rules.

That’s very different from applying for two “primary residence” mortgages in two states within two weeks. One is strategic, patient, and legal. The other looks calculated and fraudulent. Yes, timing applications close together in different states makes it harder for lenders to catch, but that’s risky if you’re in a high profile seat.

The Lender Can’t Control Your Life After Closing

Here’s the thing about owner-occupancy fraud: sometimes it’s not fraud at all, it’s just life. You may sign a document promising to live in the property for a year, but circumstances change. Maybe you lose your job three months later. Instead of bleeding cash you don’t have, you move into a friend’s basement and rent out the property to stay afloat.

Is that fraud? I don’t think so. You tried to honor the agreement, but the economy handed you a crap sandwich and you did what you had to do. And let’s be frank, no lender is sending someone to knock on your door and check if you’re still living there. They’re too busy trying to close their next loan.

Or picture this: you buy a home in San Francisco and live there for six months. Then a dream job offer lands in New York City—double the pay and a promotion. You plan to return to San Francisco someday, so you rent out the property at market rates while you’re gone. What bank has the right to tell you to leave it empty, or worse, decline the opportunity? No bank.

Life is unpredictable. Which is why there are probably thousands of cases each year that look like owner-occupancy fraud on paper but are really just people adapting to changing circumstances. The real distinction is intent: did the borrower deliberately misrepresent themselves, or did life force their hand?

You can’t really blame a borrower for thinking ahead either. Many people want to climb the property ladder whenever their finances or circumstances allow. And if the ideal home to raise a family comes along, the temptation is to seize it.

The Bottom Line

There’s a big difference between working the system within the law and outright lying to lenders. One is strategic. The other is fraud.

If the allegations against Lisa Cook are true, it’s not only embarrassing for her but also for the Fed. At the same time, the case highlights a reality few discuss: owner-occupancy fraud is far more common than people think. The incentives are strong, and the enforcement is weak.

Yes, many borrowers who lie are simply trying to save money. But if too many unqualified buyers take on mortgages they can’t comfortably afford, the risk extends beyond the individual. It puts the housing and lending industry on shakier ground when the next downturn arrives.

Readers, what are your thoughts on owner-occupancy fraud as a way to secure a lower primary mortgage rate? Should lenders tack on a 50-basis-point (or higher) premium for rental and vacation properties? And do you believe the Fed governor knowingly committed mortgage fraud just to save money?

Invest In Real Estate Without Needing A Mortgage

If you want to diversify into real estate without taking on a mortgage, consider Fundrise—a platform that lets you invest 100% passively in built-to-rent residential and industrial properties. With about $3 billion in private real estate assets under management, Fundrise primarily targets the Sunbelt region, where valuations are lower and yields tend to be higher.

As the Federal Reserve embarks on another multi-year interest rate cut cycle, real estate demand is likely to rebound. The sharp rise in mortgage rates from 2022–2025 has dramatically slowed new construction, which could lead to greater rent pressure in 2026 and beyond. That’s why it may make sense to invest today before rent inflation potentially accelerates.

I’ve personally invested over $500,000 in a couple of Fundrise funds, and they’ve been both a trusted partner and long-time sponsor of Financial Samurai. With just a $10 minimum, diversifying your portfolio into real estate has never been easier.

Subscribe To Financial Samurai 

Pick up a copy of my USA TODAY national bestseller, Millionaire Milestones: Simple Steps to Seven Figures. I’ve distilled over 30 years of financial experience to help you build more wealth than 94% of the population—and break free sooner.

Listen and subscribe to The Financial Samurai podcast on Apple or Spotify. I interview experts in their respective fields and discuss some of the most interesting topics on this site. Your shares, ratings, and reviews are appreciated.

To expedite your journey to financial freedom, join over 60,000 others and subscribe to the free Financial Samurai newsletter. You can also get my posts in your e-mail inbox as soon as they come out by signing up here. Financial Samurai is among the largest independently-owned personal finance websites, established in 2009. Everything is written based on firsthand experience and expertise.

To celebrate Millionaire Milestones: Simple Steps To Seven Figures making the USA TODAY national bestseller list, 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.
• You’re part of the richest rich class who didn’t get rich through index funds
• Upgrading to Economy Plus or even first class is no problem
• People don’t piss you off as much anymore
• You can more easily migrate to another country to save on taxes
• 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 $253,000 in Fundrise venture so far, and plan to keep investing until I build a $500,000 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 my USA TODAY national bestseller, 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.

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?

Subscribe To Financial Samurai 

Listen and subscribe to The Financial Samurai podcast on Apple or Spotify. I interview experts in their respective fields and discuss some of the most interesting topics on this site. Your shares, ratings, and reviews are appreciated.

To expedite your journey to financial freedom, join over 60,000 others and subscribe to the free Financial Samurai newsletter. Financial Samurai is among the largest independently-owned personal finance websites, established in 2009. Everything is written based on firsthand experience and expertise.

How You’ll Feel Reaching Various Millionaire Milestones ($1-$20M) is a Financial Samurai original post. All rights reserved.

When I first started Financial Samurai back in 2009, I had idealistic dreams of helping as many people as possible achieve financial freedom. My finances were crumbling during the global financial crisis, and I wanted to break free from the corporate grind. So I wrote about how to do just that.

But like anything, over time, those starry-eyed hopes fade as reality sets in: you likely won’t be able to help as many people as you imagined. And as more time passes, you realize that no matter how hard you try, you can’t help people if they don’t want to help themselves.

When I accepted this truth, a sense of peace washed over me. I stopped trying to save the world and began trusting that, in the long run, everyone will act rationally in their own best interest.

It’s Impossible to Help If There’s No Buy-In

Recently, I got an email response from a newsletter reader who said, “Thanks for your email, but honestly, it’s kind of depressing that you write about people with $5 million net worths trying to get to $10 and $15 million net worths. How many people can even just reach a $1 million net worth?”

I’ve certainly written about high-income and high-net-worth individuals before. I find the topics to be both motivating and fun. However, nowhere in my June 15, 2025 weekly newsletter did I write about multi-millionaires trying to reach decamillionaire status. Instead, I discussed:

• Benign May inflation numbers, yet the stubborn rise in Treasury bond yields after Israel bombed Iran, and Iran retaliated
• My terrible life insurance mistake that cost me a small fortune and what you should learn from it
• The reacceleration of AI interest with the Scale AI acquisition by Meta and strong IPO performance from several tech companies
• The end of being a stay-at-home dad and what I’ve learned to help other dads who are considering

I had to double-check my newsletter to find out what the reader was referring to because I couldn’t recall. And when I did, there was no mention of writing about achieving top 1% net worth figures.

But what’s more surprising is that I’ve mentioned my book, Millionaire Milestones: Simple Steps to Seven Figures, almost every week in some capacity for four months. The book is literally written to help those who haven’t achieved a million-dollar net worth get there—and then, for those who have reached the threshold, to amplify their wealth.

So, when I asked the reader whether he had read the book, he said he had not. Despite my efforts for the past 2.5 years writing and editing it, he decided the perfect book for his situation was not worth it. And that is completely fine!

However, you can’t say you’re unhappy that I’m not writing more for your situation when I’ve literally written a book exactly for your situation.

It’s Easier to Wear Slippers Than Carpet the World

In the past, I tried to meet every request. It was exhausting because everyone came from a different place. There was no efficient way to cover all topics without spending a huge amount of time writing every week.

Over time, I stopped enjoying the process because I was writing for others, not for myself. When you don’t write free, burnout is inevitable—it becomes just another job. I wanted the freedom to create on my own terms, which is one of the reasons I left finance in the first place.

You see, it’s easier to wear slippers than carpet the world. If you have a problem, it’s better to seek someone who’s faced the same issue for guidance, rather than expecting others to conform to your situation.

You can’t remove every tempting food from the world or stop processed food executives from making more poison due to the money. But you can stock your home with healthy food, find an exercise you enjoy, and build your own habits.

You can’t make other drivers better or traffic disappear. But you can leave earlier, listen to a podcast, or practice patience.

You can’t control the market or the Fed. Instead of trying to predict every move, build a diversified portfolio aligned with your goals and risk tolerance.

You can’t change a difficult boss or toxic office culture. But you can change how you respond—set boundaries, document your work, or find a new job.

Wear your slippers, folks! Your finances are your personal responsibility to get right.

Everybody Is Long-Term Rational When It Comes To Finances

Once you start focusing on changing yourself instead of trying to change others, life feels easier. And when you realize people usually figure things out for themselves, you don’t have to stress about anyone else’s money anymore. That kind of mindset brings a lot more freedom.

Here are some common examples.

1) Looking for a better asset allocation after a stock market scare

If you just went through an unpleasant bear market and are looking for a resource to help you rebalance your portfolio to match your risk tolerance, you’d just Google a proper asset allocation model of stocks and bonds by age. You’d then read the article, understand the risks and rewards, and rebalance accordingly.

You’re not just going to sit around and get pounded when the next bear market hits.

2) Drowning in credit card debt

After taking on one too many credit cards, you find yourself drowning in revolving consumer debt with a 28% APR. Instead of continuing to spend more than you make, the pain of seeing your consumer debt grow forces you to stop spending and slash expenses. The next step you’d rationally take would be to pay down your credit card debt as quickly as possible using the DAIR method.

You wouldn’t continue to spend like a maniac if you wanted the peace of mind of being debt-free.

3) Need to find a better job that comfortably pays the bills

After majoring in Art History, you’re unable to find a job making more than minimum wage. You rationally pursued this major because your parents were wealthy enough to let you enjoy your four years at a $100,000-a-year private university. Computer Science and Economics were just too hard!

However, after 18 months of being unemployed after college, your parents tell you to get a job—any job—instead of staying home playing video games. When you ask for spending money, they realize the error of their ways and tell you “no.” As a result, you rationally start applying to every minimum wage job out there so you don’t end up still living at home at age 30.

4) Surviving a layoff

After seeing dozens of colleagues get laid off over the past two years, you’re increasingly worried you’re next. Given you want to keep your job, you rationally stop playing pickleball during the workday. You also start going into the office on Fridays instead of “working from home” on the slopes or at the beach. Finally, you put in 40+ hours at your job and build strong relationships with your co-workers and boss.

If you do not adapt, your finances will likely suffer. As a result, you rationally try harder while also saving more money just in case you do get booted.

5) Retiring early without a pension

After 23 years with the same employer, you want out—but you’re afraid of losing a steady paycheck and some deferred compensation. With no pension, everything is on you to survive early retirement. Instead of just quitting your job, you rationally try to negotiate a severance package by reading a severance negotiation book. With tens of thousands of dollars on the line, there’s no way you’d just wing it during one of the most critical periods of your life.

For those aiming to retire early, there’s no way they’d settle for the national average savings rate of 5%. Instead, they’d rationally boost their savings to 20%, 50%, or maybe even 80% to get out as fast as possible.

6) Becoming a better DIY investor

After 10 years of investing in high-fee, actively managed funds in your 401(k), you run your portfolio through an investment analyzer. You’ve wondered why you dramatically underperformed the S&P 500. After seeing how much in AUM fees you’ve paid, you rationally sell all your actively managed funds and reinvest in low-fee index ETFs.

Since 80%+ of active managers underperform their indices over a 10-year period, it makes no sense to pay more for underperformance. If you continue to buy high-fee funds, it simply means you’re content with their performance and hope for future outperformance.

7) Getting bled dry from your insurance company

After discovering you’ve been paying 18–22 times more in life insurance premiums to USAA for years, you’d rationally cancel your policy—assuming you’re not terminally ill and already have a more affordable one. You’d also start auditing your monthly expenses to make sure you’re not overpaying. Nobody sticks with outrageous fees when better options exist.

If you truly feel wronged, you could wage a full-on battle online. Then you could file a complaint with the Consumer Financial Protection Bureau and expose their deceptive pricing tactics. Maybe the Bureau would step in, forcing the insurer to release audio recordings showing you weren’t willing to pay those sky-high premiums.

But if you mostly blame yourself for not watching your expenses closely enough, you might just let the issue lie—like an injured dog left to die.

8) Affording crazy college tuition in the future

While your wife is pregnant, you read a sad story about a brilliant, hard-working high schooler who passed on attending The College of William & Mary because he and his parents couldn’t afford the tuition. What a shame to not attend due to a lack of money.

Instead of hoping your kid becomes a genius or an athletic marvel who wins scholarships, you open a 529 Plan the year your daughter is born. You contribute the gift tax limit every year so your daughter can go to whichever school she wants in the future. You also ask her grandparents to contribute as well.

If you love your kid more than anything, there’s no way you wouldn’t cut expenses and start investing for her today. But if you don’t care for her that much, then sure, spending on a vacation rental when you could stay with your parents for free or buying that sweet new car makes perfect sense.

9) Losing your shirt after buying a property near the top of the market

Let’s say you bought a property at the top of the market and the house proceeded to lose 30% of its value. The Global Financial Crisis crushed your income, and it took 10 years for your property to get back to even. Given you don’t want to go through that terrible experience again, you learn to analyze properties thoroughly and follow conservative home-buying rules.

10) Not wanting to die young and rich

Your mentor of 20 years died at 62 with a net worth over $50 million. He worked 50 hours a week in banking, suffered from heart disease, and died of a sudden stroke. At 56, with a large enough net worth to generate passive income for life, you decide to cut out sugar, exercise an hour a day, and negotiate a severance to gain freedom. You wouldn’t keep working at a job you don’t love or continue eating poorly after seeing what happened to your mentor. Tomorrow is not guaranteed.

11) Not wanting to end up broke after a nasty divorce

Your friend of 18 years went through a long, ugly divorce. After 13 years of marriage and giving up her job to homeschool their kids during the pandemic, her husband left her. She was a great mom, but after 13 years out of the workforce, she was left with just basic child support and no meaningful income.

Seeing her struggle, you logically go back to work once your kids are in school full-time. You also keep your consulting skills fresh while being a stay-at-home parent. There’s no way you’re going to depend on a man for financial independence. Instead, you continue to depend on yourself, just in case.

12) Not wanting your children to flame you when they are adults and parents

One day, your kids will be grown, struggling to make it in this brutal world. And there will be a moment of reckoning—when they review how you did as a parent and provider.

• Did you show up to their school performances, or did you prioritize business trips instead?

• Why did you fight so violently with Mom or Dad in front of them instead of working things out in private?

• Why couldn’t you and Mom just stick it out until they went to college before separating? Did you really hate each other that much after having them and their sibling?

• Were you just pretending to be poorer than you were to keep them from becoming spoiled and entitled? Or did you really miss the boat and never invest in a portfolio of AI stocks near the beginning of the revolution?

You know that day is coming. The real question is: what are you doing today to make sure you have good answers when it does?

You’ll Eventually Figure Out Your Finances

As you can see from the examples, people almost always figure out a way to course-correct when things go sideways. I believe the same will happen for every single one of you reading Financial Samurai.

You’ll make changes when life gets hard enough—or when you witness something bad happen to someone else. It’s impossible not to stay on top of your finances if you subscribe to my posts or free weekly newsletter. We’re constantly tackling real issues and offering practical solutions. That’s why I don’t worry about you or your finances.

One of the most encouraging takeaways from consulting with many of you during the launch of Millionaire Milestones is just how financially prepared you already are. Every single person I spoke to was a long-time Financial Samurai reader with wealth far above the average or median for their age group.

People typically reach out because they’re facing a big decision and want reassurance they’re not missing something. I offer an honest, objective look at their finances, highlight blind spots, and map out what’s possible. That clarity gives people the confidence to take action.

We all need a little outside perspective from time to time to nudge us in the right direction. And if you don’t? That’s great too. It means you’re confident in your financial decisions and ready to keep going on your own.

So the next time you feel guilty or stressed about not being able to help someone else, take a breath and let it go. If they truly need help, they’ll find it—maybe even from you—when they’re ready.

You can’t save the world, and you’re not supposed to. The best thing you can do is patch up your slippers, keep walking your path, and be ready to help when the moment is right.

Subscribe To Financial Samurai 

Pick up a copy of my USA TODAY national bestseller, Millionaire Milestones: Simple Steps to Seven Figures. I’ve distilled over 30 years of financial experience to help you build more wealth than 94% of the population—and break free sooner.

Listen and subscribe to The Financial Samurai podcast on Apple or Spotify. I interview experts in their respective fields and discuss some of the most interesting topics on this site. Your shares, ratings, and reviews are appreciated.

To expedite your journey to financial freedom, join over 60,000 others and subscribe to the free Financial Samurai newsletter or get my posts immediately sent to your inbox by subscribing here. Financial Samurai was established in 2009. Everything is written based on firsthand experience and expertise.

Note: I’m currently on a 5-week vacation in Hawaii and won’t be taking on any new consulting clients until I return at the end of July. However, feel free to submit your information using the form at the bottom of my consulting page. I’ll follow up once I’m back and golden brown. And if you don’t want to do any of the things above, that’s all good t