Are you doing everything in your power to win the game you’ve chosen to play?

Little known fact: I am the Michael Jordan of family game nights.  Over decades of gameplay, I am undefeated across a variety of games, ranging from Trivial Pursuit to Cranium.  And like Michael Jordan, I play to win with a ruthlessness that borders on the pathological.

(This, by the way, is why I’ve vowed never to play Risk again–every game of Risk I’ve ever been involved with ends in a fight.)

But I normally don’t think about the rest of my life as a game.  Maybe I should.

I just had a mind-expanding conversation with the redoubtable Rob Siegel, the Teaching VC.  Rob asks his students at Stanford’s business school a very pointed set of questions:

What is the game you’ve chosen to play?


What is the unfair advantage that gives you an edge over everyone else?


Are you doing everything in your power to win?

Rob’s questions hit home for me.  I’m pretty darn lucky in terms of what I get to do with my life.  The work I do is pleasant, prestigious, and rewarding.  I have everything that money can’t buy.  But maybe because of that, I’ve been content to be an incrementalist.

I tinker with the levers in my life, making small changes here and there, trying to make things just a little bit better.  Since my big picture is pretty good, I’ve focused on the little picture.

Rob’s questions have me thinking that I need to make sure that I periodically think about the big picture–specifically, how I intend to spend my next decade.

What is the game you’ve chosen to play?


What is the unfair advantage that gives you an edge over everyone else?


Are you doing everything in your power to win?

Rob points out what another wise friend, Kashi Tahir, has also expressed.  I generally do things I’m comfortable with.  Fortunately, doing things I’m comfortable with has delivered pretty good results so far.  But the question isn’t whether I’ve had an impact–the question is whether I’ve maximized my impact.

Why am I Michael Jordan on game night, and Mr. Rogers in my professional life?  Maybe it’s because this is how Michael Jordan acted at times.  But there’s plenty of room on the continuum between asshole and Care Bear.

What is the game you’ve chosen to play?


What is the unfair advantage that gives you an edge over everyone else?


Are you doing everything in your power to win?

These are questions I’ll be pondering for a while.  What feelings do they evoke in you?

2 thoughts on “Are you doing everything in your power to win the game you’ve chosen to play?

  1. The hidden economy is grateful for your generousity.

  2. Very interesting post. The part about looking at the "unfair advantages" I have is honestly confronting.

    Partially I think that competitive approach to life in many parts of it sub-optimizes instead of increasing connection and happiness. It's a bit of a scarcity mentality.

    At the same time, I could look through the lens of what am I doing with the gifts I've been given and perhaps see that comparative gifts that I let lie dormant are a waste.

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