Ask a founder what they do for fun and watch the pause. It’s usually long enough to be uncomfortable for both of you.
Eventually you get the gym, or golf with a client, or “I read a lot.”
I always ask what they read, and it’s business books, so it’s still work, they’ve just moved it to the sofa.
A founder’s week gets split between the business and the family, and most founders I know would say both deserve more than they’re getting.
Whatever was left over after those two used to go somewhere, and at some point it stopped.
That leftover is what I call a side odyssey, something you do because you want to, where nobody is waiting on the result.
The word odyssey is deliberate, because the good ones take years and wander a fair bit along the way.
It’s easy to treat it as a luxury you’ll come back to once things settle down.
I don’t think things settle down, and I’ve learnt that the side odyssey will do more for you than you realize.
The longer you stay in one industry, the more it decides what you notice.
Some of that pull is easy to see, like the revenue target or the competitor you keep checking, and you can at least argue with it.
The harder part is the pull you can’t feel. You never decide against the other options. You just stop seeing them.
In 2013 a group of researchers at a Harvard-affiliated lab hid a picture of a gorilla in a set of lung scans and asked radiologists to find the small spots that could be early cancer.
The gorilla was many times larger than any of those spots.
Twenty of the twenty-four radiologists didn’t see it, and the eye tracking showed most of them had looked right at it.
I don’t read that as a story about careless doctors. Their training told their eyes where to look, it worked, and that was the problem.
The better you get at your game, the narrower the window you look through.
The only fix I’ve found is to spend time, regularly, somewhere my reputation doesn’t follow me.
Right now I’ve got three side odysseys going.
The first is qualifying for the Boston Marathon.
Boston sets a qualifying time for every age group, and even hitting it doesn’t guarantee you a place, because more people qualify each year than the race has room for.
Realistically, it’s going to take me at least two or three years to get there.
Almost everything in my working week runs in quarters, and I’m used to seeing progress by the next review.
This one won’t report back for years, and no amount of planning makes it shorter.
Nobody can run the miles for me, and no single run along the way decides anything.
Some months I’ll get faster and some months I won’t, and the only thing that moves the number is lacing up again the next morning.
The clock doesn’t care how my week went, which is a big part of why I like it.
The second was learning how to play the guitar.
I’ve swapped it for stand-up comedy, and I’m telling you that on purpose, because a side odyssey is allowed to change direction.
The guitar isn’t going anywhere, but I learnt that I needed more fun in my life. Guitar had started to feel like practice. Comedy feels like play.
The third is getting to 1000 Elo in chess, which anyone who plays will tell you is not a high bar.
Some of them have a goal, some don’t.
The goal is fine. It’s the stakes that ruin it.
If I don’t make the Boston time next year, or the year after, my business is exactly where it was, and my clients won’t know or care.
If I lose a chess game, I drop a few points and start the next one.
If a joke doesn’t land, I find out within seconds, and I get to try a different one next time.
In all three, nothing I care about professionally is on the line, so there’s nothing narrowing what I see.
That was the part I didn’t expect, that doing something with nothing on the line would widen the window again, and that I’d come back to the work seeing more than when I left.
So pick something this week where losing costs you a bit of pride and nothing else.
Put it somewhere in the calendar that work can’t reach, and treat it like a meeting you’d never cancel.
Then see what you notice once you’ve been somewhere else for a while.
Here’s Some Inner Game Wisdom to Chew on This Week
1 question from me
Are you actually building a life, or just building a busier calendar?
2 questions (and answers from me)
Q: How do I know when it’s time to quit something?
A: When staying costs more than walking away. Not in money, but in energy, clarity, and self-respect. Sometimes quitting isn’t failure. It’s wisdom.
Q: How do I know if I’m winning?
A: Look at energy, not revenue. If your battery is draining, you’re scaling misery.
3 insights
- Burnout often isn’t from doing too much. It’s from doing too little of what feels meaningful.
You can hustle 16 hours a day and still feel empty if it’s misaligned. - Your potential doesn’t need permission. It needs space.
Silence the opinions, mute the noise, and let your actual voice get some air. - Discipline without direction is just punishment.
You can be ruthlessly consistent. But if it’s on the wrong thing, you’re only getting better at going nowhere.
Get the 1-2-3 Inner Game every Tuesday
One email a week. Five minutes. One question, two answers, three insights.
Until next week:
Pick your odyssey.
Keep the stakes low.
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