We don’t stop playing because we grow old; we grow old because we stop playing.
— George Bernard Shaw
When I worked with animals, I learned a brutal lesson: they don’t tell you what they need.
You have to invent questions they can answer with behavior.
That trained me to ask better questions, not because I was clever, but because I was stubborn.
Asking the right question is an act of play: you’re poking the world to find out how it moves.
I used to hunt through tidal flats looking for anything I didn’t recognize, and then try to identify it, for fun.
Now I live the life of my customers, and argue with calendar invites.
Same impulse, different toys: curiosity.
The difference between a trapped, tired leader and a sharp, absurdly productive one is rarely talent or hours, it’s whether they still play.
Play isn’t recess.
Play is deliberate curiosity dressed as mischief.
It’s the tiny experiments you run that don’t have a KPI stamped on them.
It’s the half-serious question you throw at a team just to see what clever confession comes back.
It’s the willingness to look foolish for forty minutes so you can invent something useful for the next forty years.
It’s making that joke that everyone else is thinking about, and using levity to conquer monotony.
Fast-forward to AI and SaaS.
Prompting a model is the new tide pool: you phrase something poorly, you get nonsense; you reframe and suddenly the model surfaces a brilliant insight.
The same muscle, the willingness to rephrase, to tinker, to keep the experiment tiny, is what separates teams that move from teams that talk.
If you lead people, here are four non-pretentious, immediately usable ways to bring play back into your work so Q4 doesn’t turn into a panic theater.
Make experiments tiny and unavoidable.
Run micro-experiments that take less than a day and cost almost nothing. If it fails, you learned something faster than a committee could concoct a meeting invite. If it works, you scale it. The point is rhythm: small bets, fast feedback, no drama.
Build a weekly decision ritual.
Set a 30-minute slot where one person brings one decision, two options, and one slide. No hedging. Decide or escalate. Rituals remove wrangling and restore velocity, plus they give you time to play around the edges without burning the house down.
Turn meetings into execution, not theater.
End every meeting with two explicit things: who owns what, and when it’s due. Use automation to convert those into tasks before anyone forgets. The magic of play is discovery; the magic of leadership is turning discovery into action.
Treat tools as discipline extenders, not replacements.
AI will not save a bad process. It will magnify whatever structure you have. Use it to synthesize, simulate scenarios, or write the draft follow-ups, but first, agree on the yardstick you care about. Play the model, but keep the metric.
Now the part you actually want: a provocation, not platitudes.
If you’ve stopped playing, your calendar will tell the truth. It’s full of “update” and “review” and death by slides.
If you want to stay sharp, and please, for the love of product-market fit, do remove one meeting per week and replace it with one small experiment or a stupid question session.
Treat it as work.
Treat it with seriousness.
Watch what shows up.
I’ll go first: next Tuesday I’m asking my team to bring one absurd hypothesis about our solution and one ridiculous test we can run to prove it.
No powerpoint, just a 90-second pitch and a one-line plan.
If it fails, we laugh and move on.
If it works, we scale.
Your turn.
Tell me in the comments: what’s the last playful experiment you ran at work?
If you can’t remember, tell me what meeting you’ll cut next Tuesday and what ridiculous question you’ll ask instead.
I’ll steal the best ones, run them, and report back with results.
Play is contagious, let’s infect the whole world!
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