I hit a wall at 59.
Not a money wall — the money was handled. Forty years, ten companies, a retirement account that did what it was supposed to do. I retired from Accenture on March 1, 2024, and for the first time since I was twenty, nobody needed me anywhere on Monday morning.
That's when the real questions started. Not "can I afford this?" but "what is this?" — this being the next thirty years.
I'd spent decades answering the money question with precision. And unlike most people, I'd answered the Tuesday question too — deliberately, years before I retired: what does an ordinary Tuesday look like in a life I'm glad to be living? Nobody in the retirement-planning industry asked me that. They asked about withdrawal rates.
The Tuesday test
It starts with one exercise — the same one I did years before I retired:
Design your ideal ordinary Tuesday. Not Saturday. Not a vacation. A Tuesday — the most unremarkable day of the week. What time do you get up? What do you do before lunch? Who do you see? What work — if any — fills the afternoon? What does the evening hold?
If you can't picture a Tuesday you want, no portfolio fixes that. And if you can picture it, you've just done the most important retirement planning there is — because now every money decision has a target to aim at.
My Tuesdays, as they actually run now: coffee with Julie. The trading desk in the morning — real work, structured, with rules I wrote myself. Afternoon for whatever the day needs: the observatory, the saxophone, the grandkids, a couple of hours on the porch with my neighbor Lee putting the world right. Evening with Julie while the observatory does its thing. That's not a fantasy I pasted on a vision board. It's the life I built on purpose, one decision at a time, and it's the reason the money machinery exists at all.
Some of those passions pay — the trading desk. Some never will — the observatory. They don't have to. That's what the money is for.
Life first isn't soft — it's structural
"Design the life first" sounds like a motivational poster. It's actually the load-bearing beam of the whole plan, for a cold mathematical reason: the amount of money you need is downstream of the life you want.
Every retirement number you've ever seen — the 4% rule, the "you need $1.5 million," all of it — smuggles in an assumption about what your days cost. But nobody knows what your days cost until you've designed them. The person whose ideal Tuesday involves a workshop, a garden, and grandkids down the road needs a radically different number than the person whose ideal Tuesday involves a marina.
Get the life wrong and you get the number wrong in both directions: you either save too little for the life you actually want, or you overshoot — working years longer than you needed to fund Tuesdays you never wanted. I've watched smart people do both.
So the order matters. Life first. Then the money. Not because money doesn't matter — the next two pillars are all about money — but because money is a tool, and you don't size a tool before you know the job.
Three starting exercises
You don't need a retreat or a journal with a leather cover. You need an honest hour and something to write with.
1. The time audit. For two weeks, track where your hours actually go — not where you think they go. Most people approaching retirement discover the same thing: the job wasn't forty hours. The work alone was fifty or sixty, and then there was the scaffolding around it — the commute, the decompression, the mental overhead that leaked into evenings. You're not trying to fill fifty or sixty freed hours. You're trying to see what was already there underneath the job — and what was missing.
2. The passions inventory. Write down everything you used to love that got shelved for the career. Not aspirational — historical. The saxophone I started in fourth grade and never really put down. The telescope. The things you did at twenty-five before the promotions started costing evenings. Then mark which ones still pull at you. That's not nostalgia; that's data. The shelved passions are the raw material of the designed life — they've already survived decades of neglect, which tells you something about their durability.
3. The "enough" number. Price your Tuesdays. Not your dream life — your Tuesday life, the ordinary one you just designed. Housing, food, the car, the hobbies, a margin for the grandkids and the surprises. Annualize it. That number — not a rule of thumb, not a multiple of your salary — is the target the income streams in Pillar 2 have to hit. Everything in the next pillar hangs on this number being honest.
Why this is Pillar 1
The site is organized in a deliberate order: living your best life first, building income streams second, achieving retirement third. People always ask why the money isn't first. This is why.
Pillar 2 — the trading business, the dividend-growth portfolio, the passion that pays — exists to fund the Tuesdays. Without the Tuesdays designed, Pillar 2 is machinery without a purpose: income toward what? And Pillar 3 — the retirement math, the bridge years — is just the project plan for getting from here to the Tuesdays.
The wall at 59 wasn't a money problem. It wasn't even a planning problem — I had the blueprint. The wall was the transition itself, and no plan makes that painless. But having the blueprint meant I wasn't starting from zero on the other side. Two years of deliberate work since, and the essays and courses on this site are that blueprint written down.
Start with Tuesday. The money will know where to go.
Next in Pillar 2: why I run options trading like a business — and what "like a business" actually means when the business is you.