Petition to every HR person running Fun Fridays, especially at startups: add poker to the list.

What prompted me to write this post was a recent discussion with a few people in their first job, and something I could relate to from my own experience.

And this probably has to do with some of us idolising our teachers in school, professors in college and parents at home. Which we then tend to carry to work.

It took me a few years and a lot of wandering across startup roles to get this. Every plan a leader/manager/founder makes is basically a bet.

No matter how much conviction they perform, how certain they sound, it’s still incomplete information dressed up as a decision. I didn’t know this when I started out.

I watched founders and managers announce things with total certainty. Then the plans didn’t work out. I quietly stopped believing in them. Idolise first, get disillusioned later. It took me too long to realise that’s just what the job looks like from the outside.

The world outside is complex. Any strategy, any plan, any idea, any model, any framework, is just an attempt to reduce that complexity. It compresses reality into something digestible enough to act on, so the world can move forward. Every model simplifies a more complex reality. That’s not a flaw. That’s the whole point of a model. This post you are reading, is also a simplification of what I actually want to say.

Hell, every plan you make is a bet, but accepting that fully isn’t easy, it can feel like your world is crumbling. But it has to crumble a little, for the greater good.

Not everyone can sit with that realization easily. Almost everyone goes through a phase of analysis paralysis once they see it clearly. So many variables, so much you don’t know, and you freeze because you can’t guarantee the outcome. But once you’re through that phase, you land somewhere more useful.

If this is just how it is, why be paralysed.? Why not just FAFO!

Almost all of leadership is performance. Performance of certainty, of knowing, of having it figured out. That performance is necessary.

A team can’t move if the person leading it looks unsure all the time. But the people around that leader also need to learn how to hold uncertainty themselves, not just watch the performance and assume it’s real.

In my opinion, this definitely helps develop a better relationship between the leader and the team. Otherwise the performance of certainty just becomes another tool to maintain an illusion of control.

Poker is “probably”a good game to develop some specific muscles required in startups.

It teaches you that a good decision and a good outcome are not the same thing. You can go all in with the best hand and still lose. Play enough hands and that stops being a concept. It just becomes how you see things.

Of course, it cannot simulate the exact startup environment, but it can definitely build the psychological infrastructure underneath it: how you sit with a bet, win or lose, without losing your relationship to your own judgment. That’s not nothing!