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Once a week, I take one idea and put it under the microscope. Sometimes it’s about business, sometimes it’s about how people think, and sometimes it’s simply an observation about the world around us. If it challenges the way you see the topic, then it has done exactly what it was meant to do.

Every kid has a version of "the dream."

Mine was a garage. Not one car — a whole room full of them. Different shapes, different sounds, different decades. The kind of collection that has its own climate control and a guy whose only job is to keep everything running. I didn't have a specific car pinned to my wall. I had a vision of a lifestyle. The cars were just the most visible proof of it.

I made myself a quiet promise somewhere along the way: when I make it, I'm building that garage.

I've made it.

I haven't built it.

And I've spent more time than I'd like to admit trying to figure out why.

Growing up, my mental image of wealth wasn't a number. It was Jay Leno's garage.

The man built an entire facility that became famous on its own. Supercars, muscle cars, vintage bikes, things that cost more than houses. To me, that was the picture. That was what success looked like when it had texture — not a spreadsheet balance, not a portfolio percentage. A room full of machines that roared when you started them.

I've hit a level of freedom where I can afford most cars cash. I'm not saying that to flex — I'm saying it because it makes what I'm about to tell you more interesting. The most expensive thing in my garage right now is a powerful four-door sedan that goes fast but still fits groceries in the back.

Depending on the day, that either feels like wisdom or like I've completely lost the plot.

Before we go any further…

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The real problem is usually simpler and far more costly:

They picked the wrong business model before they ever wrote a word or spent a dollar.

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Now, as I was saying…

Here's what nobody tells you about supercars: most of them look better on a poster.

A Lamborghini only has two seats. The ride height is aggressive, which feels incredible for about forty minutes and then becomes genuinely uncomfortable. Parking it is a negotiation. Pulling out of a driveway requires you to think about whether the road ahead is smooth enough, which is an insane thing to be thinking about in a car that costs as much as a house. The insurance is punishing. The maintenance is a part-time job. Every little scratch is a five-thousand-dollar conversation.

The car you dreamed about at sixteen turns out to require enormous energy just to exist in your life.

So you rent one for a track day. You drive it for an afternoon, feel whatever you needed to feel — and then go home in the four-door sedan. The one with the back seats. The one that fits your actual life.

I kept telling myself this was the smart move. The grown-up answer. The sensible thing.

Then I came across Rory Sutherland.

Sutherland is a British ad man — probably the most respected one alive right now. He's spent a career thinking about why humans make irrational decisions.

He said this: unless you can afford to make impractical purchases, you're not really rich.

I couldn't let that go.

On the surface, it sounds like permission to be reckless. He means something sharper. If you're still running financial logic before every major purchase — calculating depreciation, checking what percentage of net worth this represents, making sure it pencils out — then money still has authority over you. You're still negotiating with it. And that's a different relationship with wealth than the one you think you're chasing.

I have a friend who married into a family with assets spread across multiple continents — real estate, restaurants, construction, probably hundreds of millions in total. He grew up broke. His dad was a sailor who was never home. His story and mine rhyme in ways that surprised both of us when we first compared notes.

Then wealth fell into his lap, and he had absolutely no framework for it.

He built a home movie theater mid-construction. Bought three electric cars and switched between them like he was rotating shoes. Invested in a building that lost money. Moved into a house with rooms that had no purpose, then spent money trying to give those rooms one.

Watching from the outside, it looked like chaos. And it was clearly bothering him — you could see it in the way he talked about these decisions afterward, always slightly defensive, like he was waiting for someone to call him out.

His wife was completely unbothered.

She'd grown up watching money move in ways that made no practical sense. That was just how it worked in her world. Impractical purchases weren't a lapse in judgment. They were proof that you'd arrived somewhere most people never do.

A Bentley Bentayga — the big SUV — runs $400,000 to $500,000 new. Four or five years in, it's worth around $100,000. That's 80% gone. People know this going in. They buy it anyway.

From a spreadsheet standpoint, that's irrational behavior.

But here's what the spreadsheet misses: when you're genuinely wealthy, financial logic stops being the filter. You buy because you want it. The depreciation is the price of admission. And if you're still running the calculation — if you're doing the mental math on whether you can absorb that loss — the calculation itself is telling you where you actually stand.

I've never spent more than 10% of my net worth on cars at any given moment. I wait for depreciation to do its worst and buy after the big drop, so I'm getting 70 cents of car for 30 cents on the dollar. I've told myself for years this is smart. Disciplined. The right approach.

Sutherland would call it the flinch.

The kid who dreamed about that garage had no flinch. He didn't calculate. He didn't weigh depreciation curves or think about insurance brackets. He just wanted the thing. The wanting was clean and uncomplicated and completely his own.

Somewhere along the way, I started running every want through a filter. Does this make sense? Can I justify it? What's the ROI on this decision?

That filter served me well. It's part of how I got here.

But there's a cost to running everything through it. At some point, the practical adult took over the whole operation, and the kid with the dream stopped getting a vote. I'm not entirely sure that trade-off was worth it.

I'm still working through this one.

There's a version of the story where the four-door sedan is genuine contentment — where I've made peace with the gap between the dream and the driveway, and the peace is real. There's another version where I've rationalized myself into a smaller life than I was aiming for.

I don't have a clean resolution.

What I do know is this: the day you stop running the calculation before every major purchase and start buying things simply because you want them — that's a fundamentally different relationship with money than most people ever develop. Whether I get there or not, I think I understand now what Sutherland was pointing at.

The impractical purchase is the proof of concept. It means the money doesn't have authority over you anymore. You have authority over it.

The Lambo might still make more sense as a rental.

But the kid who made that promise deserves a better answer than "the depreciation curve doesn't work."

P.S. If you enjoy these ideas, you’ll love the deeper conversations we have on the List Building Lifestyle podcast.