Two decades ago, I learned an important lesson: if you can’t beat them, join them. And if you can’t find a job with the monopolies, then you might as well invest in them!

Take what happened on September 1, 2025. I got an email from Apple saying my Apple TV+ monthly subscription was going up from $9.99 to $12.99. My first reaction was annoyance. Who wants to pay an extra $3 a month for the same shows? Everything should be free, like my weekly newsletter helping readers achieve financial freedom sooner!

But as a shareholder, I was pumped. A 30% price hike is massive for profitability given Apple’s millions of subscribers. I’m not going to unsubscribe due to an extra $3 a month. Then there’s the price hikes of its latest laptops and phones. This is the type of pricing power you only get when you’ve built a monopoly-like ecosystem.

The only logical thing I could think of after that email? Buy more Apple stock.

For reference, a monopoly is a market structure where a single company or entity dominates the supply of a particular product or service, giving it significant power to set prices, control distribution, and limit competition. Because barriers to entry are high—such as patents, exclusive resources, government regulation, or sheer economies of scale—the monopolist can maintain outsized profits and pricing flexibility over time.

Cash Hoards And Large Ecosystems

Traditionally, Apple’s stock sells off after its annual event where it unveils new products. The hype never quite matches Wall Street’s lofty expectations, and 2025’s showcase was no different. But Apple doesn’t need to innovate in the way we think, by launching world-changing gadgets every year. Just repositioning the camera lens 1 millimeter is good enough!

The real “innovation” is Apple’s ability to lock in customers and charge a toll. The App Store’s 30% commission is the perfect example. If you’re a developer and you want your app to succeed, you have no choice but to be inside Apple’s ecosystem. And Apple knows this. The iPhone, Mac, iPad, AirPods, Watch—all of these hardware products feed into one sticky universe of recurring revenue. Once you’re in, you don’t leave.

That’s why Apple is only going to continue dominating. As an investor, betting against Apple is betting against super-normal profits.

Google’s Monopoly Looks Good Too

Then there’s Google, another monopoly-like juggernaut. Google pays Apple $20+ billion a year just to be the default search engine in Safari. Imagine that. How can any other search engine compete when Google buys the pole position on the world’s most valuable and popular devices?

Google still commands roughly 90% of the global search market, and that dominance remains unshaken despite the rise of AI LLMs. To my dismay, Google now lifts publisher content and displays it in its AI Overviews, making it even harder for publishers to capture valuable search traffic.

In September 2025, Google was spared the worst possible judgment in its landmark antitrust case. Judge Amit Mehta ruled that while Google cannot enter into exclusive agreements with companies, it is still allowed to pay partners like Apple to distribute its services. Translation: Google can keep sending tens of billions to Apple, and Apple can keep cashing the checks.

That is a win-win for both companies—and their shareholders. It might even be a win for Judge Mehta and his extended family, wink wink. If so, Judge Mehta needs to practice Stealth Wealth instead of suddenly driving around in a Lambo and throwing parties in a new mansion.

How Many Firms Can Compete at This Level?

Only a tiny handful of firms in the world have the financial firepower to play at this level.

The only company that could theoretically compete is Microsoft, with Bing, which nobody cares about. If Microsoft ever decides to go bananas and bid against Google, we might see Apple’s annual payout rise into the $30–$40 billion range. That’s more than the annual GDP of some small countries.

From an investor’s standpoint, you root for these bidding wars. As long as Apple remains the gatekeeper of the world’s most coveted user base, it’s going to get paid.

And as history has shown, regulators and courts rarely break apart such entrenched dominance. When you have enough scale, money, and influence, you can bend politics and policy in your favor.

Strategically, Google should spend more on politicians, instead of the $20 – $30 million a year on lobbying, to protect its monopoly and gain even further ground.

The Winners Keep On Winning

This dynamic isn’t limited to corporations. It’s the same in personal finance.

Think about the wealthy individual in 2010 who had $10 million in investable assets. If that person simply plowed it all into the S&P 500 and reinvested dividends, they’d have around $57 million today, assuming the S&P 500 closes up 10% in 2025. They’ve become a semi-human monopoly—able to buy influence, provide multi-generational wealth, and secure advantages most people can only dream of.

Now contrast that with someone who bought too much home in 2006, got foreclosed on in 2010, and declared bankruptcy. Instead of compounding millions, they ended up with negative net worth and a credit rating in tatters for seven years. They’re like the small competitor trying to claw market share from Apple or Google. The gap only widens with time. The main strategy is to one day sell to Apple or Google, not compete with it.

Just like companies, individuals who already have the resources tend to keep pulling further ahead. The snowball effect is real.

Human Monopolies and Duopolies

This is why I believe investors should focus more of their attention on monopoly-like and oligopoly-like companies. If the government isn’t going to stop them—and history suggests it rarely does—you might as well benefit.

OpenAI and Anthropic, for example, are the two emerging giants in AI large language models. While both are private for now, their oligopoly structure is already forming, along with Llama and Gemini.

In consumer products, Coca-Cola and Pepsi dominate global soft drinks in a classic duopoly. If you believe the world will keep guzzling sugary beverages despite the health risks, these stocks make sense.

In payments, Visa and Mastercard form another entrenched oligopoly. If you think consumers will keep spending beyond their means and paying double-digit interest rates on revolving credit, owning these companies is a rational choice.

The pattern is clear: these entrenched players are allowed to grow bigger and more profitable while regulators look the other way. Politicians often own shares in the very monopolies they’re supposed to regulate.

So why shouldn’t you?

Adapt or Perish

Of course, disruption is always possible. OpenAI and Anthropic have already taken bites out of Google’s search business as more people rely on AI-generated answers. This is another reason why I’ve decided to invest in both OpenAI and Anthropic as a hedge.

But disruption doesn’t eliminate the monopoly dynamic—it just shifts it. Today’s upstart is tomorrow’s entrenched winner. For now, Apple, Google, Microsoft, Coca-Cola, Pepsi, Visa, and Mastercard are still firmly in control.

Companies adapt. Investors must as well. The alternative is irrelevance.

My Investing Philosophy Going Forward

For the average person, investing in a low-cost S&P 500 ETF remains the simplest and most effective wealth-building strategy. But if you’re reading Financial Samurai, you likely care about money more than most. As a result, you’re willing to think strategically about how to tilt the odds in your favor.

That’s why I like building concentrated exposure to select monopolies and oligopolies within your portfolio. These are the companies that will likely generate the most consistent profits, wield the most pricing power, and deliver the strongest returns over time. When these companies inevitably correct, I will buy the dip.

Yes, complain about injustice if you want. Yes, worry about inequality. But at the end of the day, if it’s legal and profitable, the rational investor joins the winning side. Because if you can’t beat them, you might as well invest in them.

That’s not cynicism. That’s survival.

Readers, are you investing in monopolies and oligopolies as part of your strategy? Or maybe backing startups that could one day get acquired by them? I’d love to hear your perspective—why do you think the government and courts aren’t more proactive in breaking up these giants for the sake of consumers?

Disclaimer: This is not investment advice. I’m simply sharing what I’m doing with my own money. Please do your own research, invest only in what you understand, and never risk more than you can afford to lose. All investments carry risk, and your decisions are yours alone.

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In my post, “How You’ll Feel Achieving Various Millionaire Milestones,” a commenter named Joseph shared these thoughts:

“I’m fascinated by someone worth $10M or $20M not feeling wealthy. Are they hanging out with nothing but billionaires? The only other explanation is a scarcity mindset. But I suppose that mindset got them to where they are. They need to now learn to spend! Once we hit $5M, there will definitely be a silly $150,000–$200,000 car happening. I think staring at a Porsche or Lamborghini logo will help with the not feeling wealthy thing.”

Learning how to spend is something many prodigious savers and investors have to work on. When I turned 45 in 2022, I made it my mission to start spending more to draw down my net worth. It worked, but not by intention. Thank you, bear market for losing me so much money that year!

Then at the end of 2023, I intentionally dropped a load of cash on a house I didn’t need. My thinking: I might as well live in the nicest home I can afford while the kids are still with us. Surely, the extra property taxes, maintenance costs, and opportunity cost would start dragging down my net worth. YOLO!

But the stock market had other plans. It surged in 2024 and is up again so far in 2025. Meanwhile, San Francisco real estate roared back to life, with bidding wars in the springs of both 2024 and 2025. Now we’re in a holding pattern.

It turns out that my net worth is more dependent on the whims of the markets than on any of my actions. The only reliable way to reduce it is to make consistently bad investments, and then panic-sell at the bottom. But who wants to do that? After a lifetime of investing, my instinct is to keep trying to make profits.

For spending, I can only eat so many wagyu steaks before feeling ill. My favorite retro Air Jordans cost $200, and there’s only so much closet space. I’m not into fancy $50,000+ watches or clothes, nor is my wife. Flying private is outrageously expensive, so we won’t. And I still can’t bring myself to pay a lot for a vacation rental when we’re either out and about most of the day or sleeping for eight hours a night.

Spending money wastefully requires special skill, and that is something I’m working on developing.

It’s Easy To Not Feel Rich Even If You Technically Are

If you have a net worth over $1 million, you’re wealthier than about 94% of Americans. If you’re not there yet, I will help you get there with my USA TODAY bestseller, Millionaire Milestones: Simple Steps To Seven Figures.

Cross $13 million in net worth, and you’re in the top 1% in one of the wealthiest countries in the world. You should feel rich at this level, but not always.

So why don’t more rich people feel rich?

Because it’s relative, as Joseph alluded to when he mentioned “hanging out with nothing but billionaires.”

I replied to Joseph:

Yes, there is a scarcity mindset. For example, 50% of NVIDIA employees are worth $25 million or more. Which means you’re often bumping into colleagues worth $50–$100+ million.

My softball friend who joined Figma in 2018 is probably worth $30–$50 million. But the co-founders? Worth $4–$6 billion.

It’s all relative. Living in San Francisco, the competition is fierce and so is the wealth. Best to relocate to Honolulu instead for a better life.

You’re Not Going To Blow Your Money Once You Get Rich

Unless you completely lack self-discipline, you’re going to keep making sound financial decisions after reaching the various millionaire milestones. I put the odds of Joseph actually spending $200,000 on a Porsche or Lamborghini once he hits $5 million at less than 50%. When you know how long it took to get there—and the risk and effort involved—you tend to be more judicious.

He’s either going to follow my 1/10th Rule For Car Buying or more importantly, follow my House-To-Car Ratio to ensure he’s spending responsibly. If Joseph is making $2+ million a year or owns a $10+ million home based on my 30/30/3 Rule For Home Buying, only then might he buy a $200,000 on a car.

I believe everyone is long-term rational. And rationally, everybody will do significant research before spending on such an expensive item.

I’d Much Rather Invest In My Children’s Future Than Buy A Nice Car

Case in point: Nine years of ownership later, I can’t bring myself to replace my 10-year-old Range Rover Sport with a new one for $120,000 out the door. I bought my car for $60,000 out the door, and it still gets me from A to B just fine. Yet, my net worth is much higher than it was in 2016.

Spending $120,000 on a depreciating asset just feels wrong when I could invest that same amount into a basket of growth stocks, the S&P 500 index, a rental property, or the Innovation Fund, which holds stakes in companies like OpenAI, Anthropic, Anduril, Ramp, and Databricks.

The opportunity cost of not investing feels too high. Am I supposed to YOLO with a $120,000 car that I’ll be too afraid to drive to the supermarket given it’ll get dinged up? Or should I invest $120,000 in my kids’ futures so I’ll worry less about them when they’re adults?

Obviously, any rational person who loves their children would choose the latter.

When Investing Feels Better Than Spending

At some point, you may realize you simply enjoy investing more than spending. Watching your money compound is exhilarating, especially when you get in early as an angel investor or are a limited partner in a venture fund that finds one or several unicorns. Even more satisfying is the freedom and optionality that come with greater wealth. This has been me since about 2010.

As a parent, I live with a constant low-grade worry about my children’s future. Saving and investing for them reduces that anxiety. For example, as soon as I bought and earmarked one rental property per child, my stress around housing and college costs declined.

In 5-15 years, these homes will be paid off and will:

• Provide shelter for them if necessary
• Generate rental income to pay for their college
• Offer part-time jobs managing the property
• Support my retirement

It feels good knowing my children will not be destitute and homeless, even if the world rejects them based on their identity.

So… When Is It OK To Splurge?

We’re constantly told to save and invest. Delay gratification. Let compound interest work its magic. That’s the right approach during the first half of your life.

Eventually, spending on “unproductive” things isn’t just acceptable, it’s rational, healthy, and deeply rewarding. Dying with millions in the bank would be a shame. It would mean all those hours of work and stress spent accumulating wealth went unused, when some of that money could have been enjoyed to make life richer along the way.

Here’s a framework to help you decide when it’s OK to splurge:

1. You’ve Hit Your Core Financial Goals

If you’ve:

• Built a 6–12 month emergency fund
• Maxed out retirement accounts
• Save at least 20% of your income and invest consistently
• Carry no high-interest debt

Then you’ve earned the right to loosen the reins. A $5,000 vacation or $1,500 hobby splurge won’t derail your future. It may even enhance it.

2. The Expense Aligns With Your Values

Not every return is financial. Some purchases create:

• Lasting memories
• Joy or personal renewal
• Connection with people or places

Ask yourself:

“Will I remember this in five years?”
“Does this reflect the life I want to live?”

If yes, go for it.

3. It Boosts Energy, Focus, or Time

Some “splurges” actually unlock productivity:

• Hiring help
• Upgrading your workspace
• Booking a short recharge trip

Seen through the right lens, these expenses are investments in a better quality of life.

For decades, I was too stubborn to hire help around the house. But one day, I accepted a gardener’s offer to trim all the plants in front of my home for $300 and what a difference it made. Not only did I save at least five hours of time, but the curb appeal also improved dramatically compared to when we were doing the maintenance ourselves.

4. You’ve Already Practiced Frugality For 10+ Years

If you’ve been disciplined for at least a decade, not spending can become the risk. Hoarding every dollar leads to regret, especially as time becomes your most limited asset.

Spending after years of restraint isn’t reckless, it’s rebalancing. You must practice the art of decumulation. And the best age to start decumulating wealth is around 45-50.

All the research shows that spending tends to decline after retirement and as you age. Why? Because you’re simply not as healthy or mobile to enjoy your wealth anymore. Spend more now, while you still can truly enjoy your money!

5. It’s a Small % of Your Net Worth

Simple rule: If a purchase is 1–2% of your net worth and adds real value to your life, it’s probably worth it.

Example: If your net worth is $1 million, a $10,000 – $20,000 luxury trip won’t set you back. It might actually make you feel more alive. The key is to spend the money on something you really value. Because if you don’t, even $1 is too much.

Spend With Intention, Not Guilt

The goal of wealth isn’t just to accumulate, it’s to live well. Once you’ve built your foundation, give yourself permission to enjoy your money in ways that matter.

There’s no point working hard to make money if you don’t use it to live a better life.

Personally, I care more about security and freedom than material things. Wearing simple clothes that are comfortable is just fine. Driving my 10-year-old car, so long as it’s safe, feels great. Sitting in Economy class next to my 8-year-old son is a ton of room, and we don’t get to our destination any slower than those paying 2-10X more for First. I don’t need a nice watch because my phone works just fine.

But here’s what I do value:

1. Living In A Nice Home While My Kids Are Still Living With Us

It’s always been a dream to own a home with an enclosed yard where my kids can play safely, without worrying they’ll run into the street or be approached by a stranger. So I bought the almost perfect house, even though it meant diverting significant capital away from potentially higher returns. We spend at least 15 hours a day at home, so we utilize our house more than anything.

2. A Quality Education For Our Children

This includes them becoming fluent in a second language. That type of education in San Francisco costs an arm and a leg. But it’s aligned with my values, so I’m willing to spend for now. I’m also excited about improving my Mandarin with my children over the years.

3. Great Food

Having lived in New York City and San Francisco since 1999—arguably the two food capitals of America—it’s hard not to be spoiled by amazing cuisine. And once food delivery services were perfected, we went all in, regularly ordering from our favorite local spots. The only downside to loving great food so much? A higher calorie count and a wider waistline than I’d like. No Chippendale’s dancing for me!

4. Freedom From Being Told What To Do With My Time

Most importantly, I’d rather give up a steady paycheck with benefits in exchange for the freedom to choose how I spend my time. In finance, not earning at least a $250,000 base salary feels like spending $250,000 a year for my freedom. Once I reached the Minimum Investment Threshold, where work became optional, I decided to walk away instead of suffer through the “one more year” syndrome.

Spend According To Your Values

Life isn’t just about maximizing investment returns, it’s also about enjoying the journey. Don’t be afraid to spend in ways that meaningfully improve your quality of life.

Ultimately, the goal is to align your spending with your values. If you do that, your money will always feel well spent.

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It’s a no-obligation way to have a seasoned expert review your finances, uncover hidden fees, rebalance inefficient allocations, and highlight opportunities to optimize. Greater clarity means greater confidence—and more satisfaction when you choose investing over consuming.

The statement is provided to you by Financial Samurai (“Promoter”) who has entered into a written referral agreement with Empower Advisory Group, LLC (“EAG”). Click here to learn more.

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.

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 directly in your inbox as soon as they are published 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 

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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.

I love index funds and ETFs for their low-cost nature and simplicity of ownership. However, if you want to build generational wealth before traditional retirement age, consider looking beyond just index funds and index ETFs.

Since starting Financial Samurai in 2009, I’ve written extensively about investment strategies, financial independence, and retiring earlier to do what you want.

Based on years of reader surveys and conversations, it’s clear this community is one of the wealthiest on the web. A significant portion of you have already surpassed the $1 million net worth mark, while many more are closing in. In comparison, the median household net worth in America is only about $200,000.

With this in mind, it’s time to acknowledge a simple truth: the richest people in the world don’t rely mainly on index funds and ETFs to build their fortunes. Instead, many use index funds primarily to preserve their wealth, not create it.

Why Index Funds Alone Aren’t Enough

Most of us love index funds for their simplicity, low fees, and historical returns. But if your goal is to achieve financial freedom before the traditional retirement age, or to reach a top 1% net worth, index funds alone probably won’t get you there before age 60.

To get rich sooner, you need either:

• A massive amount of income to consistently invest large sums into index funds, or
• To take more calculated risks in other asset classes

Simply put, index fund investing is best for capital preservation and slower, steadier growth. A potential 10% annual return is fantastic. But at that rate, your investment only doubles every 7.2 years. Hey, I’ll take it, and so would many of you. However, it’s simply not good enough for the richest people.

Your life is finite. Most of us only start working full time after age 18. Forty years might sound like a long time to build wealth, but trust me—it flies by. I’m 48 now, and I graduated college in 1999 at age 22. The past 26 years have zoomed past.

If I had only invested in index funds, I wouldn’t have been able to leave the workforce for good in 2012 at age 34. Don’t forget, there was a “lost decade” for both the S&P 500 and NASDAQ from 2000 to 2012. Relying solely on index funds would have delayed my financial freedom indefinitely.

Besides getting lucky, the only way to achieve financial freedom sooner than average is to take above-average risks by investing beyond index funds and ETFs. Looking back, I wish I had taken more risks.

The Average Rich Versus the Richest Rich

First off, if you’re rich—or feel rich—congratulations! You’re ahead of at least 90% of the world, which also means you’ve bought yourself more freedom than most. Although it’s tough, try not to let someone richer than your already-rich self get you down. The key is appreciating what you have.

That said, it’s important to distinguish between two types of rich, because they’re not the same. The personal finance community mostly focuses on the first kind—The Average Rich—partly because it’s easier to explain and attain, and partly because many financial creators don’t have finance backgrounds.

In fact, the lack of financial depth in the space was one of the main reasons I launched Financial Samurai in 2009. Back then, nearly every blogger only emphasized budgeting and saving their way to wealth. That’s solid advice for most people, however, I wanted to go beyond that. You can only do so much saving your way to wealth.

I wanted to escape the finance industry altogether and retire early. That’s when I started writing about FIRE for the modern worker. With the internet making it possible to earn and live in non-traditional ways, I saw an exciting opportunity to pursue a different lifestyle.

Ironically, it was 2009—during the global financial crisis—when the digital nomad trend really took off, as millions found themselves out of traditional jobs and searching for something new.

Now let’s definite the two types of rich people.

1. The Average Rich

This group includes individuals or households with investable assets between $1,000,000 and $5 million. They tend to be highly educated, dual-income professionals who max out their 401(k)s, invest in low-cost index funds, and own their primary residence.

Most of their investments are in public markets and real estate, and they typically feel financially stable but not truly rich. Some would describe this as the mass affluent class. Many started off or are HENRYs (High Earners Not Rich Yet), but then often slow down their pace of wealth accumulation once kids arrive.

You might think of the everyday rich person as someone with grey hair, a portly figure, and retiring around the more traditional age of 60–65. They’ve got a median-priced home and might fly Economy Plus if they are feeling particularly spendy. They aren’t eating at Michelin-star restaurants, except maybe for a rare special occasion, like a 30-year wedding anniversary.

The Average Rich know they’re wealthier than most, yet they still don’t feel rich. Instead, they feel closer to the middle class than to the truly wealthy.

2. The Richest Rich

These are the people with $10 million-plus in investable assets, often owning second and third vacation homes, flying first class, and making high six-figure or seven-figure investments. Their kids mostly go to private grade school, which they can comfortably afford without financial aid. They also freely donate significant sums of money regularly.

Instead of investing mostly in index funds to get rich, their money came from:

They might own index funds, but it wasn’t a driver for them to get rich. Instead, index funds are a place where they park their money, almost like a cash plus, until they find a potentially better opportunity.

20% plus or minus moves in the S&P 500 don’t phase them as the Richest Rich often experience much more volatile swings. In fact, the Richest Rich often have investments go to zero as they continuously fortune hunt for the next multi-bagger investment. So often, index funds and ETFs are a small percentage of their overall net worth (<20%).

The Richest Rich Tend To Be Seen as Eccentric

The Richest Rich are often viewed as eccentric, agitators, or downright weird by the general public. That’s because they tend to reject the status quo and do things their own way. As a result, they attract critics—sometimes lots of them—simply for not following societal norms.

They refuse to spend their entire careers working for someone else to make that person rich or organization rich. They aren’t spending a fortune to get an MBA only to work for someone else. Instead, they bet heavily on themselves through entrepreneurship and alternative investments. Index funds and ETFs? Boring. Too slow. These folks would rather build something from scratch or swing for the fences.

Many of the Richest Rich also go all-in on optimizing their bodies and minds. They train hard, eat clean, and track every metric they can—often in the hopes of staying fit enough to extend their grind and lifespan.

To most, they come across as quirky or intense. But from their perspective, it’s the rest of society that’s asleep, trapped in a system they’ve managed to escape.

Real-World Net Worth Breakdowns

Here are a few anonymized examples of the Richest Rich:

Example 1 – $30 Million Net Worth

• 30% ownership in business equity they started
• 30% real estate
• 20% public equities (65% individual stocks, 35% S&P 500 index funds)
• 15% venture capital funds
• 5% muni, Treasury bonds, cash

Example 2 – $300 Million Net Worth

• 40% ownership in business equity they started
• 20% real estate
• 20% in other private companies
• 15% stocks (half in index funds)
• 5% cash and bonds

Example 3 – $600 Million Net Worth

• 5% ownership in a massive private money management firm as one of their senior execs
• 15% real estate
• 50% in other private companies
• 10% stocks (half in index funds)
• 20% cash & bonds (~$180 million at 4% yields a whopping $6.4 million risk-free a year today)

None of them got rich by only investing in index funds. Instead, index funds are simply a low-risk asset class to them where they can park money.

Net Worth Breakdown By Levels Of Wealth

Here’s a good net worth breakdown visualization by net worth levels. The data is from the Federal Reserve Board Of Consumer Finances, which comes out every three years.

Let’s assume the mass affluent represented in the chart below is at the $1 million net worth level. Roughly 25% of the mass affluent’s net worth is in their primary residence, 15% is in retirement accounts, 10% is in real estate investments, and 12% is in business interests.

In comparison, for the Richest Rich ($10M+), at least 30% of their net worth is in business interests. Intuitively, we know that entrepreneurs dominate the wealthiest people in the world. Therefore, if you want to be truly rich, take more entrepreneurial risks and investment risks.

Time + Greater Risk Than Average = Greater Than Average Wealth

Building meaningful wealth often comes down to how much risk you take—and how early you take it. When you’re young, lean into bigger bets. Invest in yourself. Build something. Own something beyond just index funds. If you lose money, you’ve still got time to earn it back—and then some.

If I could rewind the clock, I would’ve taken more calculated risks in my 20s and early 30s. Rather than playing it relatively safe, I would’ve gone bigger on business opportunities and leveraged more into real estate. I also would’ve made larger, concentrated bets on tech giants like Google, Apple, Tesla, and Netflix. The CEO of Netflix, Reed Hastings, spoke at my MBA graduation ceremony in 2006 when the stock was only $10 a share.

In addition, I would have started Financial Samurai in 2006, when I graduated business school and came up with the idea. Instead, I waited three years until a global financial crisis forced me to stop being lazy.

But honestly, I was too chicken poop to invest more than $25,000 in any one name—even when I had the capital to put $100,000 in each before 2012. The scars from the dot-com bust and the global financial crisis made me hesitant, especially after watching so many wealthier colleagues get crushed.

Still, I still ended up saving over 50% of my income for 13 years and investing 90% of the money in risk assets, most of which was not in index funds. I’ve had some spectacular blowups, but I’ve also had some terrific wins that created a step function up in wealth.

Don’t Be Too Easily Satisfied With What You Have

One of the keys to going from rich to really rich is pushing beyond your financial comfort zone—especially while you’re still young enough to bounce back from mistakes.

You’ve got to be a little greedier than the average person, because let’s face it: nobody needs tens or hundreds of millions—let alone billions—to survive or be happy. But if you’re aiming for that next level of wealth, you’re going to have to want it more and take calculated risks others won’t.

I was satisfied with a $3 million net worth back in 2012, so I stopped trying to maximize my investment returns. Big mistake. The economy boomed for the next 10 years, and I missed out on greater upside.

Then in 2025, after another short-term 20% downturn, I shifted my taxable portfolio closer to a 60/40 asset allocation. The temptation of earning 4%+ risk-free passive income was too strong. From a pure returns perspective, that’ll probably turn out to be another mistake long term.

To balance things out, I’ve deployed a dumbbell strategy—anchoring with Treasury bills and bonds on one end, while taking bolder swings in private AI companies on the other. And you know what? It feels great. I get to sleep well at night knowing I’ve got protection on the downside, while still participating in the upside if the next big thing takes off.

Final Thought On Investing In Index Funds And ETFs

Index funds are great. I own multiple seven figures worth of them. You should too. But they are best suited for those on the traditional retirement track or those looking to preserve wealth.

If you want to achieve financial freedom faster or join the ranks of the Richest Rich, you’ll need to invest beyond index funds. Build something. Take risks. Own more of your future.

That’s how the richest people do it.

Free Financial Analysis Offer From Empower

If you have over $100,000 in investable assets—whether in savings, taxable accounts, 401(k)s, or IRAs—you can get a free financial check-up from an Empower financial professional by signing up here. It’s a no-obligation way to have a seasoned expert, who builds and analyzes portfolios for a living, review your finances. 

A fresh set of eyes could uncover hidden fees, inefficient allocations, or opportunities to optimize—giving you greater clarity and confidence in your financial plan. The richest people in the world get regularly financial checkups.

The statement is provided to you by Financial Samurai (“Promoter”) who has entered into a written referral agreement with Empower Advisory Group, LLC (“EAG”). Click here to learn more.

Diversify Your Retirement Investments

Stocks and bonds are classic staples for retirement investing. However, I also suggest diversifying into real estate—an investment that combines the income stability of bonds with greater upside potential.

Consider Fundrise, a platform that allows you to 100% passively invest in residential and industrial real estate. With over $3 billion in private real estate assets under management, Fundrise focuses on properties in the Sunbelt region, where valuations are lower, and yields tend to be higher. As the Federal Reserve embarks on a multi-year interest rate cut cycle, real estate demand is poised to grow in the coming years.

In addition, you can invest in Fundrise Venture if you want exposure to private AI companies like OpenAI, Anthropic, Anduril, and Databricks. AI is set to revolutionize the labor market, eliminate jobs, and significantly boost productivity. We’re still in the early stages of the AI revolution, and I want to ensure I have enough exposure—not just for myself, but for my children’s future as well.

I’ve personally invested over $400,000 with Fundrise, and they’ve been a trusted partner and long-time sponsor of Financial Samurai. With a $10 investment minimum, diversifying your portfolio has never been easier.

To increase your chances of achieving financial independence, join 60,000+ readers and subscribe to my free Financial Samurai newsletter here. Financial Samurai began in 2009 and is the leading independently-owned personal finance site today. Everything is written based off firsthand experience. 

We live in a world filled with empty consumeristic promises.

• To get the girl, buy this cologne.
• To be the life of the party, get this television.
• To impress your friends, buy this watch.
• To turn heads, drive this car.
• To raise a better family, buy this bigger house.

These promises bombard our senses incessantly—even within the comforts of our home. And more than we realize, these messages begin to shape our conscious and subconscious thoughts.

As a result, too often, we buy stuff we don’t need. Our closets become crowded, our drawers overfill, our garages can’t fit our cars, and our homes fill with countless products we thought were a good idea at the time; but in reality, rarely get used.

Our lives soon become buried under everything we own.

To counter these empty promises, I want to offer a simple, life-transforming question—five simple words to ask before making any purchase.

The question is this: But what if I don’t?

Whenever you feel the pull of consumerism, simply ask yourself the shortened version of this thought, “What might I be able to do if I didn’t make this purchase?”

Every purchase contains an opportunity cost. The question, “But what if I don’t?”, forces us to recognize and articulate it.

For example:

If you don’t buy that large screen television, how much debt could you pay off?

If you don’t buy the bigger house, how much more money would you have to travel?

If you don’t go clothes-shopping today, how could you build up an emergency fund?

If you don’t make this purchase on Amazon, what good could you accomplish in the world with the money instead?

You know what you’ve been promised if you buy… but what if you don’t? How would your life improve if you said ‘no?’

With every purchase we make, we sacrifice a small amount of freedom. This one, simple question helps us recognize exactly what it is.

Note: The following article was published in the June 01 issue of Simplify Magazine.

Real financial freedom isn’t about affording everything—it’s about realizing you don’t need everything.

In 2008, Memorial Day weekend promised beautiful weather—not always the case in Vermont at that time of year. So my wife, Kim, and I decided to spend the Saturday doing some shopping, running errands, and tackling our spring cleaning. Our garage was the first target.

That morning, as Kim and our infant daughter slept in, I made breakfast for our five-year-old son, Salem, and then brought him outside to help. But as soon as we started pulling out the bins, he rediscovered his summer toys and ran for the backyard. Before leaving, he asked, “Will you play with me, Dad?”

“Not now, buddy. I’ll come play as soon as I finish, I promise.”

But as the hours wore on, that promise felt more and more out of reach. I was knee-deep in stuff—cleaning it, organizing it, moving it from one side of the driveway to the other. Salem returned a few more times, asking again and again for me to join him.

At one point, our neighbor June, an elderly woman with a garden trowel in hand, watched me struggling with the clutter. She smiled and said, “That’s why my daughter’s a minimalist. She keeps telling me I don’t need to own all this stuff.”

The sentence stopped me in my tracks.

I looked at the heap in the driveway. I looked at my son, alone in the backyard.

And I realized, for the first time, the stuff I owned wasn’t just taking up space in my garage. It was taking something far more valuable: my time, my energy, my attention—and in that moment, my opportunity to play catch with my son.

That was the beginning of a journey toward minimalism for our family. And that one realization didn’t just change the way we saw our home. It changed the way we saw everything, including money.

For many, financial independence is defined by the ability to buy whatever we want, whenever we want. A new car. A kitchen remodel. A spontaneous weekend trip. We equate freedom with consumption, assuming that if nothing is out of reach financially, then we must be doing well.

But what if we’ve been aiming at the wrong target?

What if real financial freedom isn’t found in the ability to buy anything but in the realization that we don’t need to?

That shift—simple but profound—has reshaped the way I think about money, success, and what it truly means to be financially free.

The Prosperity Paradox

Here’s the problem: the more money we have, the more money we think we need. The solution the world is offering—earn more and then one day you’ll feel secure—is the exact opposite of what we need.

This is what I call the Prosperity Paradox.

Our relationship with money is one of the most defining—and often confusing—relationships we have. We earn it, save it, spend it, chase it, worry about it, and sometimes even fight over it. Some describe money as a tool—and it is. But it is also something more. It is emotional, powerful, and deeply tied to our sense of well-being.

Consider this: 77% of people in the wealthiest country on earth report feeling anxious about money.[1] And more than 70% say their desire for more money influences their daily decisions.[2] That’s not just a tool. That’s something that touches our heart and mind in profound ways.

The Prosperity Paradox says this: The more money we have, the more money we believe we need.

This isn’t theory—it’s backed by data. Empower recently surveyed Americans and found that those making over $200,000 a year said they would need an additional $150,000 annually to feel financially comfortable.[3] Charles Schwab, in another study, found that 87% of millionaires don’t consider themselves wealthy.[4]

We can see this in how people define what it means to be “rich.” For many, the word “millionaire” signals success. But the closer one gets to that number, the less likely they are to view it as true wealth. In fact, millionaire status is now considered by many to be “just getting started.”

This paradox plays out again and again: retirement targets growing as net worth increases, happiness tied to ever-larger income brackets, and comfort levels that seem always out of reach. The more we accumulate, the more we convince ourselves we need.

Even John D. Rockefeller, once the richest man in the world, when asked how much money is enough, famously replied, “Just a little bit more.”

If our goal to achieve financial freedom is simply to accumulate more money, we will never arrive. The finish line keeps moving.

That’s why this realization—that needing less is more powerful than earning more—changes everything.

Becoming Minimalist

But that raises the important question: if the common approach to financial independence doesn’t deliver on its promise, what does?

For me, the answer came that very weekend in 2008, when my neighbor June introduced me—almost accidentally—to the idea of minimalism. Her words sparked a realization that would change the way I viewed not just my possessions, but money itself.

Real freedom doesn’t come from purchasing power—it comes from the realization that we don’t need more in the first place. And once we stop needing more, we stop spending more. That’s when everything changes. That’s when peace and clarity show up—not in having more, but in finally wanting less.

When we own less, we begin to see how little we truly need. And when we stop needing more, we stop spending more. Suddenly, financial independence doesn’t feel like something reserved for the wealthy—it feels possible, right now, with what we already have.

Minimalism helped reveal this truth to me. The less I owned, the less I needed. The less I needed, the less I spent. The less I spent, the freer I felt. And with every unnecessary item I removed from my home, I began to remove financial pressure from my life.

Abundance in Less

It’s understandable why “spend less” is a hard sell. For most of our lives, we’ve been conditioned to think that spending less is a sacrifice. In a culture that defines success by accumulation, the idea of buying less sounds like going backward.

That’s certainly what I used to believe—until I actually tried it.

I made the intentional decision to own less and buy less. And it remains one of the best decisions I’ve ever made. It didn’t just improve my finances; it improved nearly every part of my life.

Owning less meant fewer things to clean, maintain, insure, and replace. It meant fewer distractions and more focus. And it meant I could put my time, money, and energy toward the things that actually matter.

Life didn’t get smaller when I started spending less. It got bigger.

I had more freedom, not less. More clarity. More purpose. And I found myself more present in the things that bring lasting fulfillment—my family, my faith, and the opportunity to help others.

In short, spending less didn’t feel like I was depriving myself. It felt like I was discovering greater abundance—in the truest sense of the word.

And here’s what’s most important: this isn’t just possible for a few. It’s available to all of us.

Financial freedom doesn’t begin with acquiring more money. It begs with having less desire for money.

Becoming Content

This isn’t to suggest that money doesn’t matter. It does. Money provides shelter, food, warmth, and care. It can be used to do good in the world. It can bring stability and security.

But money alone doesn’t bring freedom. Contentment does.

The Harvard Business Review published a study by Ashley Whillans showing that people who prioritize time over money report significantly greater well-being—more fulfilling relationships, more joy, and more satisfaction. Contentment, not accumulation, is the key.[5]

Contentment isn’t about settling for less. It’s about appreciating what already is. It allows us to stop chasing “more” and start building a life that aligns with what matters most.

Here are some principles that can help bring this new vision of financial independence closer:

Define what is truly “enough.” Rather than letting culture or comparison dictate our financial goals, we can take time to define what we genuinely need to live a meaningful life. And often that number is far less than expected.

Lower fixed costs where possible. Housing and transportation are two of the largest expenses for most households. Downsizing or driving a paid-off car can create breathing room in the budget—and in the soul.

Break the habit of lifestyle inflation. When income increases, it’s easy to spend more. But each upgrade delays freedom. Choosing instead to let increased income create margin, not upgrades, moves us closer to peace.

Find joy in simplicity. A home-cooked meal, a walk around the block, a quiet evening—these are often the richest moments. And they don’t cost very much.

Be generous. Generosity interrupts the cycle of always needing more. It reminds us that abundance is not about accumulation but about impact. And it grows contentment every time it’s practiced.

Avoid the comparison trap. Someone else will always have more. But comparison is a thief—of joy, of gratitude, and of purpose. Financial independence isn’t about outperforming others. It’s about being free from the need to.

Make a Choice

When we stop tying freedom to a number and begin tying it to values, everything begins to shift. We stop asking, “How much do I need to be free?” and start asking, “What can I remove that’s keeping me from freedom today?” That’s the realization that changes everything.

Financial independence becomes less about someday and more about today. It becomes less about stock market returns and more about a satisfied heart. It becomes less about accumulation and more about intentionality. And slowly we begin to see that maybe the finish line was closer than we thought.

In the end, we all want the same thing: to live with peace, to care for the people we love, and to spend our days on what matters most. And maybe—just maybe—that future begins not with a raise or a windfall but with a decision. To own less. To want less. And to walk in freedom now, not later.

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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 

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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

Spending money is an American pastime. With a national saving rate hovering around 5%, it’s clear we collectively love to spend. And honestly, being able to enjoy our wealth is a beautiful thing. It’s something more personal finance enthusiasts like me—and readers of Financial Samurai—could probably do more of.

But like with most things, moderation is key. Overspending can trap us in the rat race forever. It can increase our anxiety about job security or unexpected health issues as we live paycheck to paycheck. And if you have kids, excessive spending might even put them at a long-term disadvantage, creating a cycle of financial stress.

In this post, I want to share a personal experience that helped me understand just how emotionally difficult it can be to stop spending, even when we know we should.

That Sinking Feeling of Being Judged

After dropping our kids off at parkour class, my wife and I took a stroll to Haight-Ashbury for some ice cream at Ben & Jerry’s. It’s a nostalgic spot I first visited back circa 1993 on free cone day with a line several blocks long. Jerry Garcia from the Grateful Dead was still alive, and he was performing that day.

On our walk over, we passed funky odors and colorfully dressed folks who had just finished the Bay to Breakers race. When we finally reached the store, I asked the attendant if they had any unique flavors unavailable in grocery stores. She pointed to a sorbet, but we wanted ice cream.

Then came the sticker shock: $8.75 for one scoop, $13 for two. A waffle cone? Another $3.75. My frugal brain screamed, “This is insane! You can get a whole pint on sale for $5!” But I felt too embarrassed to back out in front of my wife. So I caved: one scoop in a waffle cone, $14 total.

We enjoyed it—triple caramel chunk—but I felt like a fool. On the walk home, I turned to my wife and said, “I’m never buying Ben & Jerry’s waffle cone ice cream again.”

The Shame of Not Spending

I didn’t stick to my frugal instincts because I didn’t want to look cheap. Even after years of being together, I still didn’t want to disappoint my wife.

This wasn’t just about ice cream. I had told her for several months that I was open to renting a house in Hawaii for our upcoming five week summer trip. When the stock market tanked in early April 2025, I figured, why not spend the money instead of losing it all in the stock market? At one point, we were down around $1 million, a gut-wrenching amount for dual unemployed parents. She agreed. YOLO and decumulate, right?

But the cheapest 4-bedroom single-family home rental I found that we both liked was $24,000 a month after taxes, utilities, and fees. Yikes! That’s a lot when we could just stay at my parents’ house for free. Sure, it’s not ideal for privacy and puts a lot of pressure on my mother as a host, but it’s great for family bonding. And $24,000 invested in our kids’ custodial accounts today could more than double to $50,000 in 11 years at a 7% return. That could help pay for college or help them buy a home.

My wife was disappointed, and I don’t blame her. Living with in-laws isn’t easy. And she knows that hosting is especially hard on my mom, who needs her space—something that’s tough to maintain with six people under one roof, especially when two of them are particularly loud and rambunctious. My wife is also the planner for all of our travel logistics, so my indecision was starting to frustrate her.

But I just couldn’t get myself to pull the trigger, even if it is within my vacation spending guide. I felt bad for letting my wife down. If you’re curious, below is the picture of the $24,000/month rental. Cute, right? But not for $24,000/month.

Tried to Spend Again After Several Big Wins

After about 35 days of painting, de-weeding, staging, and prepping our old house post-tenants, we finally sold it for a solid profit. Selling a home is often a stressful process, but we accepted a preemptive offer after a couple rounds of countering and ultimately hit my target price.

I used about 70% of the proceeds to buy the stock market dip over a 50-day stretch. First we were losing, which felt horrible given the home was such a stable investment. Eventually, the S&P 500 clawed back its full 20% loss, and I locked in gains on half our position. Our allocation for this important portfolio shifted from 100% stocks to a more balanced 60/40, as the S&P 500 returned to trading at 22X forward earnings—an expensive level in my book.

To top it all off, Millionaire Milestones made the USA TODAY bestseller list—a distinction earned by only ~0.04% of authors. I spent 2.5 months grinding away on marketing through guest posts on CNBC and MarketWatch, publishing related content on Financial Samurai, running consulting promotions, and giving interviews.

Surely, this triple win deserves a little celebration, right? I was exhausted after working so hard and taking so much risk. So I floated the idea of renting a house for a month again. YOLO, baby!

So Hard to Find Value When Booking a Vacation

My wife was cautiously optimistic. But as I searched more, I still couldn’t justify spending $24,000 for that house we looked at earlier because I really wanted a pool if we were going to shell out big bucks. Unfortunately, homes we considered with pools and views were going for $50,000 to $85,000 a month. A ridiculous sum of money. No thanks.

My wife could have cared less about a pool. She just wanted somewhere clean with two bathrooms, AC, a kitchen, and laundry that we could have to ourselves. Then we could have planned meals and family time with my parents at their convenience.

The thought of spending $24,000 on rent for just one month stung deeply, especially since I haven’t been a renter since 2002, when I was 25 years old. On top of that, it was emotionally draining to buy the dip and watch losses pile up for three to four weeks straight. Parting with that hard-earned cash felt too psychologically and financially painful.

I’m in the process of grinding back to financial independence given we bought an expensive home in 2023 and used much of our dividend income investments to do so. This realization was only made after I published this post and had some time to think about the feedback.

Took My Dad’s Advice About Spending

I even asked my dad for advice since there are a lot of vacation rental scams out there too. During the stock market crash, he said, “Stay with us.” After the recovery, I showed him new options, and he still said, “Stay with us.” So I listened, as any good son would.

As a result, we will save $24,000 on rent and now have $800/day to spend on food, activities, and more. That feels amazing! All we can eat poké here we come! But I could tell my wife wasn’t as thrilled. Ah, the feeling of disappointing her again despite the wins we had.

Ice Cream as Emotional Compensation

So when the Ben & Jerry’s attendant asked, “How many scoops?” I flashed back to all of this. I felt ashamed that I couldn’t follow through on the vacation rental. I’m the provider, gosh darn it. I didn’t want to let my wife down again. So I said yes to the overpriced cone at least.

But afterward, I still felt stupid. I knew I could get a more delicious matcha soft ice cream in a waffle cone at the mall for $6.90, or half the price.

Spending $14 on ice cream was my emotional Band-Aid for not spending $24,000 on the vacation rental. But it didn’t fully patch the wound. I still feel like I need to do more.

As someone who grew up middle class with frugal parents, there’s simply no way I can justify spending that much on a temporary living arrangement with no equity. I’ve spent too much of my life focused on building wealth, not spending it.

Besides, at least 70% of the joy of being in Hawaii comes from just being there, enjoying the weather and outdoors. I don’t plan on staying inside for most of the day.

Fear Of Being Judged Is Why We Overspend

This experience helped me realize something important: We often spend money not because we want or need to—but because we don’t want to be judged, especially by loved ones. Even after 26 years together, I still didn’t want to disappoint my wife.

Unlike some personal finance or FIRE enthusiasts, I don’t take being called or viewed as cheap as a badge of honor. Instead, I take offense to it because I’m fully spending my money according to my values. And we don’t all value the same things, so who is anybody to judge?

This need to appear generous, carefree, or successful may push us to spend more than we should. Our insecurities lead us to waste money on things we don’t value. We’re not always spending for joy, we’re spending to protect our image.

I don’t care what others think, only what my wife and children think. As men, we often work tirelessly to provide for our families, yet there are still moments when we feel like it’s not enough.

Related: Feeling Like A Burden Is A Terrible, Terrible Thing

The Solution to Overspending

The next time you feel pressure to spend, pause and revisit your core values and financial goals. If you don’t know what they are, figure them out—fast. Ask yourself: Does this expense align with who I am and what I want for my future? If the answer is no, then don’t spend. Love yourself enough to follow your values.

And if you’re in a relationship, talk it through. Being on the same page financially is important for a successful, long-term partnership. The last thing your partner wants is for you to be grouchy or regretful after spending. At the same time, you don’t want to let your partner down and feel constrained, especially if you have the funds. Resentment will only build.

In our case, the compromise I came up with is to spend weekends at my aunt’s beach house on the other side of the island to give everyone some breathing room, assuming she’s okay with that. The only problem is my aunt hasn’t said yes, yet! She’s traveling.

Another solution is to spend one or two nights at a beachfront resort in Waikiki or Kahala. I’m open to booking a Saturday night so we can make the most of the facilities on both Saturday and Sunday. Maybe we should do Friday night as well, but the kids get out from summer school at 3:30 pm on Friday, so is it really worth it? Perhaps I’m being too frugal again, but at least I’m offering up solutions. That’s progress!

Achieving Financial Freedom Is Worth The Price

Thanks to all your thoughtful feedback, I decided to write a follow-up post titled: “The Choices We Make To Achieve Financial Freedom Aren’t For Everyone.” I was able to retire in 2012 at age 34 because I made hard choices to save and invest.

What I’ve realized is that frugality is deeply ingrained in me. It’s not just a habit, it’s who I am. As a result, I find it hard to spend money on anything that doesn’t align with my values, even when I technically can afford to.

After being a homeowner since 2003, I simply can’t bring myself to pay rent—especially not for a luxury rental I don’t need. On top of that, I’m laser-focused on hitting financial independence by December 31, 2027. I made a detour in 2023 by buying a home we didn’t need, which knocked down our passive income by roughly $150,000.

Now, I’m on a mission to rebuild our passive income so it once again covers 100% of our desired living expenses. That’s why I’m not only saying no to a five-week rental this summer—I’m kicking off a no-spend challenge too. I love a good financial reset, and this one’s going to fuel me to save and invest even more for our family’s future.

With AI innovation picking up speed again, I’m also aiming to deploy more capital into private AI opportunities. One of the easiest ways I’m doing this is through Fundrise Venture, which has exposure to top-tier AI companies like OpenAI, Anthropic, Databricks, Anduril, and more.

Readers, do you think we mainly overspend because we are not secure with ourselves? Why do you think it’s so hard to stop spending despite knowing we should be saving and investing more? Is it silly to let other people judge us for how we spend our own money? What choices are you making to accelerate your path to financial freedom?

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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.