Retirement, Wealth, and the Surprising Struggle to Spend

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In the world of personal finance, there’s a common assumption: when you finally achieve financial independence, you’ll finally start spending like someone who’s made it. Fancy dinners, plush hotel suites, front-of-plane seating, spontaneous travel, and artisanal groceries from Whole Foods without blinking at the price. Surely that’s what freedom looks like, right?

Well, as one early retiree recently discovered, reality plays out a little differently.

Let’s step into the life of a man who reached financial freedom early, gave himself permission to start living a bit more lavishly… and still ended up underspending by most standards.


A Wealthy Experiment in Lifestyle Inflation

A few years ago, the man behind a popular early retirement blog decided it was time to challenge his frugal instincts. He had done the work—earned, saved, invested, retired early—and now, it was time to enjoy the spoils.

He kicked off his lifestyle upgrade by buying a Tesla. Not exactly a reckless purchase given his financial position, but certainly a symbolic one. It was a gesture of transition: from ultra-optimized frugality to a more relaxed, abundant mode of living.

“Look at me!” he joked at the time, imagining himself as the enlightened version of his former frugal self. “I’m adjusting my habits like a real badass. Time to live the Good Life.”

And for the next two years, he did just that.


Flights, Festivals, and Fancy Food

From that point forward, spending started to feel more like a tool for experience rather than a habit to be avoided. He traveled widely, attended EDM concerts with his son, explored immersive art exhibits like Meow Wolf, and embarked on spontaneous road trips—one of which took him from sunny Tempe, Arizona to the bright lights of Las Vegas on Christmas Day.

As a newly single man with a wide-open schedule, he embraced freedom in full color. He met new people, caught up with old friends, and allowed himself the luxury of saying “yes” without filtering every decision through the price tag.

His approach to food evolved too: gone were the rigid grocery budgets and price comparisons. If he happened to be in a Whole Foods instead of Costco or Sam’s Club, he’d pay the markup and move on. Dining out was chosen for ambiance and enjoyment rather than discounts and coupons. Flights were no longer about finding the cheapest possible fare, but about minimizing discomfort—an upgrade to what he called the “reduced torture” seats.

Surely, with all this spending, his budget must have skyrocketed.


The Budget Reveal: A Surprise Twist

But when he finally tallied up a year’s worth of spending—not for the sake of guilt, but out of curiosity during a coaching session with a friend—the truth stunned even him.

His total spending had grown… but only modestly. From a previous baseline of around $20,000 per year, his new spendier lifestyle reached about $30,000.

That’s it. A full lifestyle shift, Tesla included, and he still couldn’t push his annual budget into the realm of typical American consumption.

How?

The answer lies not in frugality, but in intentionality. Even when actively trying to spend more, his instincts leaned toward value. He didn’t deprive himself—he just didn’t default to excess. He bought what he needed, paid for what he wanted, and made peace with a little extra indulgence. But all of it was grounded in conscious choices.

It’s also worth noting that he lives in a paid-off home and has no debt. His nest egg—bolstered by years of strong stock market performance—could easily support a six-figure lifestyle. Yet he finds it difficult to spend even a fraction of that, simply because he doesn’t need to.


The Deeper Truth: Abundance Isn’t Always Expensive

Perhaps the most enlightening takeaway from this little social experiment is that once you’ve trained yourself to find joy in life’s essentials—relationships, movement, nature, learning, freedom—more money doesn’t drastically increase your happiness. It just gives you options.

That road trip? It was fun not because of the gas money or the Vegas hotel, but because it was shared with his son. The Meow Wolf experience was magical not because of the entry fee, but because of the creativity, surprise, and human connection.

More money can amplify experiences, but it rarely creates them from scratch.


What Comes Next? More Experiments, Of Course

Even with this modest increase in spending, he’s not done. The goal wasn’t to “get it right” on the first try, but to explore the boundaries of comfort and value. With abundance as a mindset rather than a budget line, he’s looking forward to more lifestyle experiments in the years ahead.

Nearly two decades into early retirement, he’s still learning. And he invites others to do the same: not just to count dollars and chase returns, but to step back and reflect on what actually delivers the most meaning.

Maybe that’s a trip with your kid. Maybe it’s giving yourself permission to buy the good coffee. Or maybe it’s realizing, after all these years, that you’re happiest with less.


Final Thoughts: Optimization Without Obsession

There’s something deeply liberating in knowing you could spend more… and choosing not to. Not from fear or scarcity, but from a sense of satisfaction and clarity.

So here’s to financial independence—not as a finish line, but as a starting point for experimentation, joy, and yes, even the occasional luxury seat on a flight to somewhere new.

After all, what’s the point of all that financial freedom if not to live life on your terms—even if those terms turn out to be surprisingly simple?

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