Blended Tribes

Right before I moved to Panama, a good friend asked the question that everyone eventually asks: when are you going to retire?

I'd just been diagnosed with AFib. I told him straight, I was done with the full-time grind, but I wasn't done working. I wanted to build something new, on my own terms, and nothing was going to stop me.

Turns out retirement was never really the goal. It's an escape plan, and it only makes sense if you're running from something. I wasn't.

This one's about the four rules that replaced it for me: knowing my real number, setting my hours before the work sets them, keeping my right to say no, and holding onto one piece of work that's still mine even on the days the money doesn't show up.

New Maps, Purposefully Designing for the Full Arc of a Working Life Retirement was built for a shorter life. Mine isn't one.

New post today about developing good taste.

I realize that sounds dangerously close to me claiming I have good taste.

So, for legal purposes, I would like to remind everyone that I once owned and voluntarily wore a gray denim duster similar to Clint Eastwood’s in the 1985 movie Pale Rider.

The argument: taste isn’t inherited. It’s built.

Your Taste Was Never Inherited You weren’t born with an eye. You built one.

My wife and I are learning Spanish again, and she is kicking my ass. It also means I’m remembering how uncomfortable it can be to be bad at something in public.

The older we get, the more used we become to knowing what we’re doing. Being a beginner messes with that. It asks us to look foolish, ask dumb questions, and let go of the need to seem competent.

Stoicism, ego, and the strange freedom of being willing to suck at something for a while.

Allow Yourself to Be a Beginner Again Blank stares and the freedom to fail

AI can make you feel capable of almost anything.

Build a website. Edit video. Write code. Create content. Set up automations. Offer consulting.

That's dangerous.

New post: why AI expands your options and why more options can sometimes make the business decision harder.

I Accidentally Invented an Agency The gap between what you can do and what you should do

I’ve wanted to write this one for a long time, but it took me a while to figure out how. I hope you like it.

The Slow Meal What a long meal with someone you love actually asks of you

Three teenage girls on the Panama Metro taught me something about vanity, self-respect, and the danger of trying too hard to look like a local.
I thought my Panama hat would help me blend in.
It didn't.
My latest post is about what the Stoics can teach us about personal style, why I still wear the hat, and a simple test that can keep unnecessary clothes out of your closet.

Why I Still Wear the Panama Hat What three teenage girls and Epictetus taught me about vanity

Most of us use AI to move faster.

I recently used it to do the opposite.

When I discovered serious problems with the handling of my immigration case, every angry instinct in me wanted to react immediately. Instead, I gave myself 40 days to slow down, separate emotion from fact, and figure out what to do next.

In my latest post, I share the five-part prompt I used to challenge my assumptions, identify what was reversible, uncover my blind spots, and make a calmer decision.

Sometimes the smartest use of AI isn’t getting an answer faster.

Sometimes it’s helping you wait long enough to ask a better question.

How I Use AI to Slow Down Before a Hard Decision The Stoic case for letting a difficult choice sit and the five-part prompt that helps me think clearly

"A jack of all trades is a master of none, but oftentimes better than a master of one." Most of us have heard some version of that line. I always assumed it was one old saying. It's actually three, stitched together over four hundred years, and the meaning flipped every time somebody added to it.

That history sent me somewhere I didn't expect: straight into the question of what mastery actually is, and whether anyone ever really gets there.

I used to think mastery was a finish line. Cross it, and you're done. But nobody who's actually good at something describes it that way. The better people get, the more clearly they see how much they still don't know.

So I've started thinking about my life less like one skill to perfect and more like a garden: a few things that need daily water (character, health, the people I love), a few that need weekly attention (the writing, the business), and a few that are allowed to just grow slowly, or stay hobbies, without ever needing to pay rent.

I wrote the full 400-year history and the philosophy behind it here:

Jack of All Trades A 400-year detour through an old proverb, and what it taught me about a mastery that never finishes

My grandmother could look at a plain table for thirty seconds and know exactly what it needed. Two things, chosen well, never more than that: a bowl moved six inches to the left and a bouquet with three stems cut shorter than the florist intended. She was French Canadian, not wealthy, and never once mentioned money while she taught me this.

Watching her taught me what taste actually is: attention, paid consistently, over years, to small things nobody's grading you on.

Here's the rule I still use, the one I got from a woman who's been gone forty years. Before I buy anything, I ask what it would look like if I owned three and had to pick the best one. Usually that question kills the purchase entirely.

What My Grandmother Taught Me About Wanting Less The Stoic case for taste as a form of attention, and the one rule I still use before buying anything

An old colleague from my design and construction days emailed me last month asking if I'd consult on a project remotely. Easy money, he said.

Ten years ago I'd have said yes by the second paragraph, then spent the next hour building an elaborate excuse to justify why I had to back out.

This time I typed five words. "That doesn’t work for me," and then I sent the email. I thought to myself, was I being too impulsive? Maybe even a little rude? I sat there for a full minute, waiting for the follow-up question that would force me to explain myself.

It never came. He wrote back, "No problem, good luck out there." Turns out most people just want an answer. The excuses were for me, not for them.

You’ve Earned the Right to Say No Without a Reason The Stoic case for a clean no, and the one line I finally learned to use