Forget Long Term Strategic Planning

We serious adult types really value planning and prepping and researching and approaching problems in a well-considered manner.  We also overestimate our own ability to plan and predict the future, and our efforts to do so can be a big hindrance on living a good life.

When you’re thinking not just of the next move, but a long sequence of moves and counter moves based on the probability of how others will respond, you get into some pretty dicey territory.  If you are an expert chess player, this is exactly how you want to play (or so I’ve heard).  It works because chess is bounded.  There are only so many moves, and when you’ve mastered the game you can quickly narrow down the variables and predict the set of options several moves out.  The squares, pieces, and rules of movement are the same, move after move, game after game.

Imagine a chess board that, as you were pondering and planning a long sequence of moves, changed shape?  Then a third player joined with her own pieces, and those pieces didn’t move by the same rules.  Then the pieces started talking to each other and your Rook quit and joined the white Queen to form an independent alliance.  Then the black Pawns invented machine guns…you get the point.  This is more like life.  There are way too many variables and complexities to plan many steps ahead.

There are some big benefits to taking a more modest approach.  I was recently reminded of a great TED talk about the spaghetti and marshmallow tower challenge.  Teams are given some sticks of dry pasta, a bit of tape and string, and a marshmallow and have a time limit within which to build the tallest tower with a marshmallow on top.  Apparently, MBA’s are pretty bad at the challenge, and little kids are pretty good at it.  The MBA’s spend all their time working on the single perfect plan, then build it and place the marshmallow on top just as time expires.  Then it collapses.  They have so much discussion and prep and detailed delegation of tasks that the plan becomes very rigid, and every single part has to work perfectly or the whole thing will (literally) crumble.

The kids take a different approach.  They just started building immediately.  The throw together small structures and put the marshmallow on top.  Then they take it apart and make a bigger one.  They are rapidly prototyping.  They just start learning about the pieces and possibilities in front of them by directly engaging with them.  They plan no further than the first idea that comes to mind.

I heard a podcaster say she always loses to her young daughter in Jenga for the same reason.  She’s so focused on the position of the blocks five moves from now that she doesn’t always make the best decision in the moment.  Her daughter keeps it simple and lives in the moment, always plucking the safest possible piece on every turn.

That’s how I manage to survive playing tennis with my wife, who actually knows how to play the game.  I know I lack the technique and strategy she has, so I simply go all out to return every shot and just keep it in play.  I figure at some point she’ll make a mistake.  Plus, when I try to get tricky and set up a sequence of shots, it usually goes wrong.

There is overlooked value in the novice approach.  Just taking in the resources currently before you and fully diving in to the problem at hand has major advantages over long deliberation and planning.  When you’re a kid or a novice with nothing to lose, why not take a stab?

We may gain expertise in many things and develop the ability to plan into the future with greater detail, but we shouldn’t mistake expertise at a single thing like chess or tennis for expertise at life.  In life, we are all novices.  We’ve never (as far as we know) lived before, and we have no idea what will happen at any moment.  The way you might plan a single, solitary event like the construction of a house (if you’ve ever done that, you know that never goes as planned either!) doesn’t translate to the span of your life.

Take some pressure off of yourself and don’t stress about what Job A or School B next fall will mean for your retirement account 40 years down the road.  You have no idea.  No one does.  Take stock of your loves and hates, do more of the former and less of the latter, and seize on the best opportunities before you.  If it’s not working, take a lesson from the prototyping kids.  Adapt, grab the sticks, and try a different approach.

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