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.

Get A Free Financial Analysis From Empower

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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.

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Wanting is the menacing margin of error between desire and need. It is the blade that vivisects your serenity, the hammer that shatters your wholeness — to want anything is to deem your life incomplete without it. It is a perpetual motion machine that keeps you restlessly spinning around the still point of enough. “Enough is so vast a sweetness, I suppose it never occurs, only pathetic counterfeits,” Emily Dickinson lamented in a love letter a century before Kurt Vonnegut, in his shortest and most poignant poem, located the secret of happiness in the sense of enough. Wanting is a story of scarcity writing itself on the scroll of the mind, masquerading as an equation read from the blackboard of reality. That story is the history of the world. But it need not be its future, or yours.

An epoch after John J. Plenty and Fiddler Dan — John Ciardi’s magnificent 1963 spell against the cult of more — author Martine Murray and artist Anna Read, living parallel lives close to nature in rural Australia, offer a mighty new counter-myth in The Wanting Monster (public library) — an almost unbearably wonderful modern fable about who we would be and what this world would be like if we finally arrived, exhausted and relieved, at the still point of enough. Having always felt that great children’s books are works of philosophy in disguise, speaking great truth in the language of tenderness, I hold this one among my all-time favorites.

The story begins in a town so tranquil and content that no one notices the Wanting Monster, who stands sulking on the edge of the scene, part ghost out of a Norse myth, part Sendakian Wild Thing.

And so the Wanting Monster stomps over to the next village, “bellowing and crashing about as monsters do,” but still the magpie keeps singing, the bees keep laboring at the flowers, and the children keep playing in the square. The Wanting Monster redoubles the growling and the howling, but not even Billie Ray, “the littlest child of the village,” pays heed.

This inflicts no small identity crisis:

What good was a monster if it couldn’t raise any trouble? If it couldn’t even raise the eyebrow of a small, curly-headed child? The Wanting Monster had its head in shame.

But then it comes upon Mr. Banks, napping serenely by the stream. With that “terrible compulsion” that turns the insecure monstrous, the Wanting Monster moans its siren growl of want into the sleeping man’s ear.

Mr. Banks began to wriggle. His heart began to jiggle.

A little note of misery sounded in his mind.

What could possibly be wrong?

It was a perfect day for a snooze by the stream. But now he wanted something else, something more.

Suddenly, he wants the stream itself, shimmering so seductively in the sunlight that it has to be had.

As soon as Mr. Banks builds a swimming pool at his house and fills it with the stream’s water, Mr. Bishop perches to peek over the fence and begins “to twitch and prickle and hop around” with the restless desire for a pool of his own.

So goes the cascade of envy, that handmaiden of wanting, until pool by pool the streams begins to run dry.

Soon it was only a trickle.

The fish gasped and flapped, the frogs jumped away, and the reeds withered and died.

Triumphant and drunk on its own power, the Wanting Monster now wonders how much more damage it can do to these peaceful people. So it turns to Mrs. Walton next, who is gathering flowers in the field for her dear friend Maria, and whispers into her ear.

Mrs. Walton began to frown and fret.

She was irritated. Why was she picking flowers for Maria when it was really she herself who deserved them?

She should fill her own house with flowers.

Yes, she should have the most fragrant, the most colorful, the most stylish house in the whole village.

Everyone would admire it. Everyone would envy her.

The other women watch Mrs. Walton pick all the flowers she can carry, and suddenly they too are aflame with the mania for owning the flowers. Soon, no flowers are left and the bees are bereft of pollen, the butterflies fly away, and the wrens and finches have nowhere to nest.

The Wanting Monster stomps across the flowerless fields, gloating.

That night, it visits Mr. Newton — the town’s most passionate stargazer — and whispers into Mr. Newton’s ear.

Suddenly possessed with the desire to own the stars, he heads to the forest and cuts down a great old tree to build himself a ladder, then climbs into the night and takes a star.

I am reminded here of this miniature etching by William Blake, which I suspect might have inspired Read’s art:

Ms. Grimehart watches Mr. Newton and, unable to bear possessing no stars herself, she cuts down not one tree but two to make an even bigger ladder and snatches not one star but five.

More and more ladders rise up and the sky soon grows starless. With the stream gone and the flowers gone and the forest gone, with the birds silent and the bees still, this tranquil little world finds itself unworlded.

The village was quiet and colorless and gloomy. The children wept. They had loved their forest and their little stream. They missed the singing birds, the sunlit flowers, the shining stars.

People, unable to console the children, begin to leave. The Wanting Monster roars with self-congratulation.

This time, everyone hears the roar and begins to wonder about the menacing presence. It is Billie Ray who first sees it and, pointing, tells the townsfolk that there is a monster in their midst. Naming a hurt has a way of opening up the space for healing — as soon as the little girl names the menace, everyone sees it clear as daylight. Suddenly, the Wanting Monster grows “no bigger than a beetle.” It is only those things of which we are not fully conscious that have the power to possess us.

But when the grownups lurch to stomp the tiny monster, Billie Ray stops them, leans down and asks the suddenly helpless creature if it needs a cuddle.

The Wanting Monster climbed into the palm of her hand. It was tired, after all, and the hand was soft and warm. It lay down. Billie Ray cupped her other hand to make a roof, and then she wandered toward the dry river bed, where she sat on its banks and began to rock her hand and sing the lullaby her mother had once sung to her.

No one had ever sung to the Wanting Monster before. Nor had it ever been cared for. And the Wanting Monster didn’t know quite how those things felt — not really.

Listening to the lullaby, the Wanting Monster begins to weep. “There, there,” Billie Ray comforts it, “Oh, dearest heart.” The Wanting Monster doesn’t know how to bear all this tenderness — how many of us really do — and so it goes on weeping “sorrowful, endless tears” that begin replenishing the stream.

Everyone else, listening and watching, begins to weep too.

A great mournful lament filled the valley.

Tears swelled the little stream, and it rushed like a river…

What had been withheld was released; what had dried up, flowed.

What had hardened was becoming soft again.

People unpack their suitcases, take the stars out of their pockets, and set about collecting seeds, tilling the ground, and filling watering cans to replant the trees and flowers.

As the birds return and the night reconstellates, the Wanting Monster finally stops weeping and, looking up wonder-smitten at the stars lavishing the world with all that abundant beauty, feels, finally, slaked of want.

Couple The Wanting Monster with The Fate of Fausto — Oliver Jeffers’s kindred fable inspired by Vonnegut’s poem — then revisit Wendell Berry on how to have enough.

Illustrations courtesy of Enchanted Lion Books; photographs by Maria Popova