The Wrong Ruler

Ross Perot had enough money to stop forever. The fact that he kept going didn’t prove anything about me exactly, except this: I had already decided what I would do with that much money, and his choice exposed the gap between his wiring and mine.

I remember the ’92 election mostly as a pile of commas.

Clinton. Bush. Perot.

And Perot’s money.

I don’t remember exactly when I first heard the number, but sources put his fortune around $3 billion back then. I remember doing the napkin math, because that is where my brain went immediately.

Five percent on $3 billion is $150 million a year.

That’s $12.5 million a month.

About $411,000 a day.

Around $17,000 an hour.

Without touching the principal.

That number broke something in my understanding of people. Not because I couldn’t imagine having the money. I could imagine that part just fine. What I couldn’t imagine was still wanting to work.

If I had that kind of money, I thought, I’d be gone.

Beach. Plane. Margaritas. Following the Dead. New cities. Dumb grins. No boss. No meetings. No “next phase.” No “bigger vision.” No need to prove anything to anyone ever again.

Give me the interest stream and I’m out.

So I couldn’t understand Perot. Why would a man with that kind of glide path choose more work? Why run for president? Why put yourself through all that noise when the money had already solved the problem?

And then the answer came in sideways.

That’s exactly why I’ll never be a billionaire.

I don’t think like one.

Perot wasn’t staring at the interest and thinking, “How do I stop?” He was thinking, “What’s next?”

Not better. Not worse. Just different wiring.

My default question has always been: How do I get free enough to enjoy this?

The builder’s question is different: What can I build next?

That gap explains a lot of my life.

I like the man’s money. I do not like working for the man.

That’s not exactly a business plan.

When I’ve had money, I’ve liked living like I had money. Nice house. Good food. Books. Trips. The freedom to say yes without doing a full-body financial scan first. I am not above comfort. I’m not even close.

What I don’t like is earning money the way money usually wants to be earned.

The meetings. The decks. The performance. The fake urgency. The alignment. The strategic whatever. The adult costumes.

I did those jobs. I watched people from that era keep going. Some of them became Fortune 100 CEOs and killer consultants. They could swallow the pose. They could hold the face. They could play the game without choking on it.

I couldn’t.

I’d start feeling like something was being vacuumed out of my ribs. Then I’d leave. Move. Travel. Start over. Do something that felt alive.

Great stories.

Bad compounding.

That’s the trade.

And it is a trade. That’s the part I don’t get to dodge anymore.

I’m 60 now, with two very young kids and two teenagers, and the ledger is louder than it used to be. I’ve had a ridiculous run of adventures. I’ve lived a lot of life. I’ve seen places, started over, followed impulses, taken the scenic route, burned years like they were extra.

And on paper?

Not much to show for it.

That’s where the wrong ruler comes out.

I’ll look at money people and measure myself against them. I’ll carry the billionaire’s ruler around like it belongs to me. Net worth. Houses. Freedom. No boss. No worry. Time fully bought and paid for.

Then I forget the part where I refused the billionaire’s entry fee.

The focus.

The grind.

The tolerance for boredom.

The public risk.

The relentless building.

The ability to keep doing one thing long after the interesting part is over.

I wanted the pile without the machine that makes the pile. I wanted the lifestyle without the wiring. I wanted the reward without becoming the kind of person who would keep chasing the next thing after the reward arrived.

Not flattering.

True.

Teaching is my third career, and no, it isn’t some pure calling. I dislike big chunks of it. The bureaucracy, the performative adult language, the forced enthusiasm, the systems pretending to be smarter than they are. Put me in a room full of adults and the phoniness gets thick fast. Holden Caulfield would need a leaf blower.

And I’m not exempt. I’m an old phony now too. I know that.

But the kids are the part that isn’t fake.

In a classroom, the costume drops for a few hours. Kids cut through things. They may be ridiculous, distracted, loud, and allergic to instructions, but they are usually not pretending to be polished adults in a meeting about deliverables.

That’s why teaching beats the other suits.

Not because it’s easy. Not because I’m noble. Because at least some part of it feels real.

Back to Perot.

In 1992, my fantasy was simple: give me that interest stream and I’ll coast forever.

Today the fantasy is older, but the skeleton is the same. I still don’t want titles. I don’t want a corner office. I don’t want to win LinkedIn. I don’t want to be important in a room full of people pretending the room matters.

I want time.

I want mornings with my kids.

I want to travel slowly.

I want to camp, go, look, eat, nap.

I want money as oxygen, not identity.

That’s the actual game.

The problem is that I keep borrowing scoreboards from people playing a different one.

If your real game is money, status, scale, conquest, fine. Pay the price. Plenty of people do. Some even seem built for it.

But if your real game is presence, autonomy, pleasure, family, time, and enough room to breathe, then stop acting shocked when you don’t win at someone else’s game.

That’s the part I have to keep relearning.

Define enough.

Not as a vibe. A number.

What does the family-first life actually cost? What monthly nut gives us room to breathe without grinding me into paste? What is the boring, repeatable path to that number?

Not billionaire money.

Not fantasy money.

Enough money.

There’s dignity in that, if I let there be.

There’s also a contradiction I probably just have to live with: I like living rich, and I hate most of the roads that get you rich. That tension doesn’t disappear. It just needs boundaries so it doesn’t run the house.

Time keeps scoring whether I admit the rules or not.

’92 turned into kids’ car seats, then “Can I take the car?,” then somehow back into car seats again. The bank curve stayed flatter than I’d like. The stories got good. The tradeoffs got real.

Some days I can hold all that without flinching.

Some days I can’t.

But I know this much: the wrong ruler will ruin a decent life.

It will make every good day look small. It will make a full table look empty. It will make time with your kids feel like failure because it didn’t also turn into a yacht.

That’s insane.

Common, but insane.

So if you’re lugging around the wrong ruler too, try this:

Name your actual game.

Put a number on enough.

Stop letting people who want different things set your scale.

And if you really do want what they want, fine. Pay the price on purpose.

Either way, own it.

For the record, the napkin math still makes my eyes pop. Five percent on $3 billion is $150 million a year. More than enough to fund almost any lifestyle I can imagine.

But it turns out money was never the only question.

The question was what kind of day I’d want once I had it.

And I think I’ve known that answer longer than I’ve wanted to admit.