In 2024 I had a plan I was fairly sure would work.
I’d just left a long run in the advertising business, and I had time, a network, and the particular restlessness of a man who’s always had a next thing. The idea was simple and sound: find small agencies whose owners wanted out, buy them, and roll them up into something bigger. I knew the industry. I knew the people. I could see the spreadsheet in my head before I’d opened one. I could do it.
I didn’t. I remember saying it out loud, more or less in these words: I could do it, and I’d do it for what? For money? I’d said, not long before, that more money wasn’t going to buy me the freedom I was after. A rollup buys a lot of things. Freedom wasn’t going to be one of them.
Most of what gets written about agency is about the engine. How to stop waiting. How to act before you feel ready. I believe all of it, and I’d want Addie and Kins to have it. But an engine on its own is a dangerous thing to hand anyone.
Agency without judgment is just efficient ambition. It builds the wrong thing beautifully.
You’ve met people like this. I’ve been one. Brilliant at getting things done, fast, relentless, admired. They climb in record time and arrive somewhere they never meant to go. They build a company that eats their marriage. They win the promotion that takes them away from the years with their kids. Every step was an act of agency. The whole was a life nobody would choose.
The missing part has a name. On the old steam engines there was a device called a governor: two weighted balls spinning on a shaft, rising as the engine ran faster and easing the throttle back so it held a steady speed. It made the engine last, and it held it at the speed the work needed.
People have a governor too. The question is who’s setting it.
For most of us, most of the time, somebody else is. Fear sets it, keeping the throttle low so we never risk looking foolish. Other people’s scoreboards set it, keeping us flat out at games we never chose. Or nobody sets it, and the engine runs at whatever speed the day demands until something breaks.
Aristotle had a word for setting it yourself: phronesis, usually translated as practical wisdom. It’s the judgment to know what this particular situation asks of you, now, and the steadiness to act on it. It’s the word our family put at the root of everything we do.
The best governor I have isn’t mine alone.
Early in 2025 I had another plan, a better one than the rollup: a fund that would invest in the game I’d grown up in. The market was there. The network was there. On paper it was everything I’d been building toward. I walked Lex through all of it, the vision, the opportunity, why the timing felt right.
She listened. Then she asked one question.
“What does the travel look like?”
A fund like that, done properly, means regular travel. Investors, deals, the companies you back. Plenty of people do it well and still put their families first when they’re home. But I’d done the arithmetic on our time with the girls a few months earlier, and I knew what “regular travel” would cost in days I’d never get back. Lex held up a mirror: is this version of this opportunity worth those specific days?
It wasn’t. Not then. Without that one question I’d have talked myself into it, and I’d have told myself some travel wasn’t that much.
That’s what the governor looks like in a marriage. It’s the person who sees you brush your teeth, asking the question you were too excited to ask yourself. You can perform for colleagues and clients. You can’t perform for her.
Here’s what a governed life looks like from the inside, in my experience. It looks slower than it is.
It says no more than it says yes, and the noes are the most productive thing in it. It chooses a few games and plays them all the way. It’ll go flat out when the moment calls for it, a deadline, a crisis, a season of building, and then it eases off on purpose, because the moment has passed and the family is at the table.
The values we claim to hold are only real when they cost us something. The rollup would probably have made money, and the fund might have been the best thing I ever built. Both would also have spent the years when Addie and Kins still want to be picked up and dropped off at school, and no spreadsheet turns those back into cash.
So I lean on one question more than any other: does this deserve me, now? It sets aside what I’m good at and asks whether the thing in front of me deserves me, at this point in my life, given the people and commitments I’ve chosen to protect. Most days the answer is yes and I get on with it. Some days it’s no, and those are the days that shape a life.
The governor can be wrong, and mine has been. Judgment is a practice too: you decide, you move, and reality tells you how you did.
One small thing to try this month.
Name one thing you’re genuinely good at, something you’d win at if you kept playing. Then ask it the question, out loud if you can: does this deserve me, now?
If the answer is yes, go at it with everything you’ve got, and stop second-guessing it.
If the answer is anything short of yes, keep going for now, and stop feeding it by reflex this week. See what fills the space. And if you have someone who sees you brush your teeth, ask them the question too.
— Daniell