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Retirement might never come for you
June 21, 2026
I was out for dinner last week. Nothing special, just a local place I like. A few tables over sat a guy, maybe mid-forties, the polished kind you see in IT leadership. He was there with his wife and two kids. And the whole time, his phone owned him. Work, from the look of it. His daughter kept tugging his sleeve. His wife said something to him twice. He nodded without ever looking up.
I keep seeing this. Not the phone exactly, everybody has a phone. I mean the quiet thing underneath it, where the people who are supposed to matter most get a little less of someone every week, and nobody actually decides to let that happen. It just happens.
So why do we work like this?
Honestly, I think most people are scared. Scared they’ll hit some age without enough money to stop. And here’s the strange part. Most of them have never once sat down and figured out what “enough” even is. Noah Kagan calls it your freedom number. A real, computed figure, the amount that buys your way out of needing a paycheck from anyone else. Most people carry the fear and skip the math.
I want to tell you the thing I wish someone had told me when I was a kid.
Retirement has almost nothing to do with the pile of money you build over a career. It has everything to do with how you live. Reading that, you probably think, well, obviously. But sit with it for a second, because almost nobody believes it in the way they actually run their days.
You can retire right now. You should, actually. I’m not telling you to quit your job tomorrow. I’m telling you to look hard at what you’re trading and what you’re getting back for it.
Here’s roughly how I’d map it now, if I were starting over:
- Single. Build the lifestyle that lets you move. Be a digital nomad, see the world, go out too much. Make something you’re proud of. Work absurdly hard and rack up a pile of mistakes worth telling stories about later.
- Married, no kids. Travel, and don’t let your costs creep up to match your income. No car loans. No mortgage, you have to feed. Save 30% of everything in actual cash, split four ways. Life. House. Cars. Kids’ education.
- Married with kids. Get real healthcare coverage in place. A 9-to-5 is fine once you’ve learned to manage your own energy, which mostly means you don’t come home wrung out. Ever. Give your hours to your kids, your spouse, your friends. Find a couple of people you trust and build the dream project together. And point the work at things that actually fit who you are.
- Kids in college. Drop the 9 to 5. Go all in on the projects you care about.
- Your older years. Write about what you lived. Teach what you figured out. Keep building.
So where does retirement start?
Nowhere. That’s the whole answer. It doesn’t start because it was never a date on a calendar. It’s a way of living you carry throughout. The freedom to keep collecting experiences along the line of your life. Someone sold us the idea that it’s a financial finish line, and we bought it. Try building your life so the question quietly stops mattering.
And the money? The universe is stranger and more connected than we give it credit for. The cleanest way I know to earn is to let the money fall out of work you’d do anyway. A byproduct of the passion projects, not the point of them.
About the guy at the restaurant.
I ended up talking to him for a minute. I asked what the single most important thing in his life was right now. “My family, of course,” he said. I told him I didn’t believe him, and I walked off. I caught the blank look on his face as I turned. No idea if I’ll ever see him again. But something landed in that half-second. The only question is how long it stays landed.
Here’s the part that connects to the work I do.
Even when we never sit down and rank our priorities on purpose, something in us keeps score anyway. Call it the universe, call it gut, whatever you like. We know when we’re making a bad trade. We feel it before we can explain it. And living out of step with that signal, year after year, hardens into a low hum of worry about whether we’ll be okay down the road. That gap, between what we sense and how we actually live, is the front edge of burnout.
Cheers!
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