Tennis, Psychadelics, and Entrepreneurship

I’ve always thought of tennis as perhaps the most difficult of sports.  It’s like hitting a baseball, but while you’re running, and with 90% of the addressable target area out of bounds (in the net, outside the lines, etc).  To top that off, you’re a team of one, battling yourself, inside your head.  So it’s really easy to get frustrated and implode when things start heading south.

I played a lot of tennis as a kid, but basically haven’t played at all for the past 15 years or so, until recently.  Over the past few weeks, I’ve picked it back up and gotten really into it, and it’s been really fun and also a challenge.  My playing style has always been aggressive and error-prone.  I have (IM*H*O) beautiful strokes, but go for a lot of winners and tend to make a lot of unforced errors.  Historically, I often lose to players who can simply get the ball back and put me in a position to beat myself.  On serve: it’s aces or double faults.  You get the idea.

Clearly, this is a frustrating way to play, and to be.  And it puts me into a position to love and hate tennis at the same time, and to get really down on myself for not living up to what I see as my potential.

Recently though, I’ve been working on a way to address this.  I’ve been going into playing tennis expecting it to be frustrating, and knowing that overcoming that frustration is part of the challenge, and part of the fun.  Seems like a subtle difference, but it’s really been game-changing for me. If I go in expecting to have a mental challenge — and knowing that I’ll get through it — rather than being surprised when it happens, it’s somehow way easier to deal with.  It becomes part of improving my game, just like working on my strokes, and it generally helps me relax and get loose, rather than get frustrated and tight.

This may seem like a stretch, but it reminds me of what a good friend once said about eating magic mushrooms: that it’s a challenge and an adventure;  that he fully expected to get freaked out and scared, but working his way through that, and getting over it, is part of what he liked about it.  Seems crazy in some ways, but I get it.  So, I guess I’m saying playing tennis is kind of like tripping on mushrooms.

And of course, it’s the same with being an entrepreneur.  Apparently Reid Hoffman characterized entrepreneurship as “throwing yourself off a cliff and building a plane on the way down”, which feels right.  And my friend Nick has described the roller-coaster ride of entrepreneurship — one day you feel like you’re killing it and you’ve got the whole world figured out, and (literally) the next day, you can feel like you’re 100% wrong and totally screwed.  That’s for real — in the past, I’ve felt it on something like 8-hour cycles — and it’s part of the reason why co-founder chemistry is so important; to help you weather that storm.

In all of these cases, I think the trick is not letting yourself feel like all is lost — expecting there to be (sizable) bumps, but understanding that of course there are, and that’s part of the challenge and part of the fun.  Somehow, thinking about it that way really changes things for me.

 

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