The retirement industry will answer one question for you, in exhaustive detail: do you have enough money?
It will not answer the question that matters more: enough money for what?
I retired on March 1, 2024, after nearly forty years — from the Air Force in 1984 through ten companies including Dow Chemical, Applied Biosystems, Oracle, and Accenture (twice) — most of it lived out of a suitcase. I had the spreadsheet: the Monte Carlo simulation, the withdrawal plan, the tax strategy. And unlike a lot of retirees, I had the other half too — trading, music, church, family.
But the life design — the part most people never even think about — is the most important thing. So let's start there.
Retiring from vs. retiring to
Most people retire from something. From the grind, the travel, the boss, the 6 a.m. flights. That's a fine reason to leave. It's a terrible plan for arriving.
Freedom without direction doesn't feel like freedom for long. It feels like drift. The calendar empties, and for about three weeks that's glorious, and then the quiet starts asking questions you can't answer with a portfolio balance. I've watched smart, successful people hit this wall. They did everything right on the money side and walked straight into an identity crisis, because their job was the last thing that told them what to do on a Tuesday. A friend of mine didn't hit a wall — he spent over a year wading through a thicket. Not a crisis, just twelve months of trying things on and taking them off, because he'd never thought it through ahead of time. He got there. He just paid a year to learn what he could have known before he left.
Here's the reframe that fixed it for me: don't retire from something. Retire to something. And figure out the "to" before you go, not after.
The good-Tuesday test
Forget the bucket list. Bucket lists are vacations — they're the highlight reel, not the life. The question that actually matters is smaller and harder:
Describe a perfect ordinary Tuesday in your retired life. Not a vacation Tuesday. A regular one.
What time do you get up? Who's at the breakfast table? What do you do at 10 a.m., at 2 p.m., at 7 p.m.? Who do you talk to? What did you make, fix, learn, or finish by dinner?
If you can't answer that, you don't have a retirement plan. You have a resignation plan.
My Tuesday, for what it's worth: up at 8:30 — I'm a night owl, always have been, and retirement means I don't pretend otherwise — coffee with Julie, then the markets and the trading book. It's a business; it gets business hours. Afternoons, most of the year, belong to the fifteen acres: there's always something out there that needs doing. Grandkids when they're around, dinner with Julie. Roughly once a week there's a Potler day — my neighbor Lee and me on the porch with cold drinks, discussing life. (Butler + Potter = Potler.) The observatory gets the clear nights; the saxophone gets a couple of sessions a month. Nothing exotic. That's the point. The best life isn't exotic — it's yours, on purpose, repeated.
The time audit
You can't design the life until you see the one you have. So here's the homework — two weeks, one notebook:
Write down where your hours actually go. Not where you think they go. Actually. The commute, the scrolling, the meetings that could have been emails, the evenings that evaporate between dinner and bed.
Most people find two things: they're spending far more time than they realized on things they don't value, and the things they claim to care about — the hobby, the people, the health — are getting the leftovers. That's data, not judgment. But it's the most important data in this whole exercise, because it tells you what your life is currently for. And whether that's what you want it to be for.
The passions inventory
Separate exercise. Write down everything you'd do with a free month — not a free month of money, a free month of time. Then cross off anything that's really just "rest." Rest is recovery, not purpose; you need it, but a life built on rest is a waiting room.
What's left is your inventory. Mine: variable-star astronomy (twenty-plus years, nearly seven thousand observations and counting), the saxophone (since fourth grade — some things you just never quit), trading (the puzzle that pays), church, teaching (this site exists because of it). None of these appeared after I retired. They were all there for decades. Retirement didn't give me passions. It gave my passions their time back.
That's the thing nobody tells you: you don't find yourself in retirement. You fund the self you already are. If the inventory is empty now, no amount of money fills it later. Start filling it while you're still working — an hour a week beats a blank page at sixty-five.
The people test
Last question, and it's the one that cuts deepest: who do you want more hours with?
Not "who do you love" — that's easy and useless. Who gets your hours? Name them. Then look at your time audit and see if the names match the hours. For most working people, they don't — not even close.
For me it's Julie, the kids, the grandkids — and then the next ring out, deliberately: the neighbors — Pat and Lee (Potler days don't schedule themselves), our church small group, the worship band I play sax in, and the longtime friends we make a point of getting in the car to visit. Grandkid time isn't a line item in a retirement spreadsheet, but it's the highest-return investment I hold. Everything on this site — the income streams, the trading, the planning — exists to buy more of those hours. If your plan doesn't name the people, it's a math project, not a life plan.
Why this comes first
This site has three pillars: living your best life, building income streams, and the retirement math that makes it all sustainable. This one comes first, because the order matters:
Living Your Best Life is the why. Building Income Streams and Achieving Retirement are the how.
The income streams mean nothing without a life they're funding. The retirement math means nothing without a Tuesday worth paying for. Design the life first — the good Tuesday, the inventory, the people — and then build the money to fund that, specifically. Not "retirement." Your Tuesday.
Everyone's answers are different. That's the moat — nobody can copy mine, and I can't copy yours. What I can give you is the questions. The answers are yours to write, and the sooner you start, the better the life gets.
Don't wait until you get there. Know what it looks like before you arrive.
This essay is the cornerstone of the Living Your Best Life pillar. The other two pillars — Building Income Streams and Achieving Retirement — are the machinery that funds the life you just designed.