The Wrong Ruler

I remember the ’92 election mostly as a pile of commas. Clinton, Bush, Perot—and Perot’s money. Sources put his fortune around $3 billion then. At a plain 5%, that throws off $150M a year ≈ $12.5M a month ≈ $411k a day ≈ $17k an hour, without touching principal. Why keep grinding when the interest alone buys the world?

Here’s where my brain went then (and honestly, often still goes): if I had that pile, I wouldn’t work. I’d live like a rock star—beach, planes, chasing the party, margaritas, following the Dead, dumb grins in new cities. Not a “serve the republic” phase. Pleasure, autonomy, no boss. So I couldn’t understand Perot: why would anyone with that kind of glide path choose more work?

And then it clicked: that’s exactly why I’ll never be a billionaire—I don’t think like one. He wasn’t counting interest; he was counting the next thing. Not moral, not immoral—just different wiring. My default question was “How do I stop and enjoy this?” His was “What do I build next?”

If you want theory for that split, a few frames actually help:

• Freud’s pleasure vs. reality principle. The pleasure principle pulls toward immediate gratification; the reality principle delays it for bigger payoffs. My needle tilts hard to pleasure and work-avoidance; the builder type channels discomfort into projects and keeps going.

• Present bias (behavioral econ). We overweight “now” and underweight “later.” I value the beach today more than the bigger account later. Builders discount the present less—today’s slog is fine if it buys tomorrow’s runway.

• Weber’s work ethic. Our culture still hands out status for relentless building. If that story hums in your bones, coasting feels like decay; if it doesn’t, coasting feels like freedom.

The hedonic treadmill shows up too. When I’ve had money, I’ve loved living like I had money—nice house, good food, buy the books, go places. That part fits me. What doesn’t is earning it the way the earning tends to happen. I like the man’s money; I do not like working for the man.

There’s also the autonomy piece (self-determination theory). When work feels controlled and performative, I feel like something is being vacuumed out of my ribs. I did those jobs for years. Friends from that era kept swallowing it; now they’re Fortune 100 CEOs and killer consultants. They could hold the pose. I couldn’t. I’d start choking on the meetings, the decks, the “alignment,” and leave. Then I’d do something that felt alive—move, travel, start over. Great stories, bad compounding.

Fast-forward. I’m 60 with two very young kids and two teenagers, and the ledger is loud. I’ve had a ridiculous run of adventures and, on paper, nothing to show for it. This is where the “yardstick” beats me up: I carry the billionaire’s ruler but refuse the billionaire’s entry fee. I want the lifestyle and the pile without the grind and the tradeoffs it actually costs. That’s wanting something for nothing. Not flattering. True.

Teaching? Third career. Not some pure calling. I dislike big chunks of it. But the kids are the part that isn’t phony. Put me in a roomful of adults and the performance gets thick fast—the kind of stuff Holden Caulfield would point at and call “phony.” I never fully grew out of that. I’m an old phony myself now, sure, but in a classroom the kids cut through the costume for a few hours. That’s the only reason it beats the other suits.

Back to Perot. In ’92, my fantasy was: give me that interest stream and I’ll coast forever. Today, the fantasy is older but same skeleton—buy time, not titles. Swap the rock-and-roll loop for a family loop: travel with my kids, camp, go, look, eat, nap. Still no desire to “hustle” for some ladder I don’t believe in. Money as oxygen, not identity.

So what do you do with that? A few stakes I can live with:

• Admit the price tag. If you won’t pay the billionaire fee (time, focus, tolerance for tedium, public risk), stop grading your life with a billionaire’s yardstick. That ruler will make every decent day feel small.

• Name the actual game. Mine is pleasure + presence + autonomy. When I forget that, I start wanting someone else’s life and hating the one I picked.

• Define “enough” in numbers. Not vibes. A monthly nut that funds the family-first life without grinding me into paste. Then build the most boring, repeatable way to hit it.

• Accept the contradiction. I like living rich and I hate the usual roads that get you rich. That tension doesn’t vanish. 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 into “Can I take the car?,” then back into kids in car seats for the babies. The bank curve stayed mostly flat. The stories got great. The tradeoffs got real. Some days I can hold all that without flinching; some days I can’t.

If you’re also lugging the wrong ruler around, try this: write down your real game, set a number for “enough,” and stop letting people who want different things set your scale. If you do want what they want, then pay the price on purpose. Either way, own it.

(And for the record, the napkin math still makes my eyes pop: on $3B, 5% is $150M/year—more than enough to fund almost any lifestyle. It just wouldn’t change what I want to do with my days.)