The fallacy of long-term planning

What do you want to do with your life? Make a five-year plan? Talk through your vision with a mentor? After having windy conversations for years and being asked for advice on these things, I almost reflexively now try to return someone's focus to the basics.

In startup world, this is your powerpoint planner with the perfect pitch who can't stop perfecting it. This isn't real work -- it just makes you feel like it is. Make a @#$% product. Put it out there. Get real people paying small amounts and telling you why it's shitake mushrooms. The hard part is recognizing that the planning is easy -- and people love doing what's easy.

In chess, a hard learning has happened for me in much the same way, in every format. Whether it's climbing to 2500 bullet against the fastest players in the world, or now working my way through the ranks in long-form tournament games, I needed to have a reckoning with myself about the b.s. of long-term planning.

Some of the beauty in chess no doubt revolves around generating long-term positional plans, but that's like looking at a book and saying, "I love the concept of going from chapter 4 to chapter 37." It's enjoying the idea of reading over the reading itself. You pack a book for vacation and read six pages on the plane. In chess, those 30 in-between chapters are ruthless combinations, series of micro-plans to gain small, barely imperceptible advantages. Then combining those advantages, maneuvering your pieces to the right squares, neutralizing your opponents' ideas as they meld with your own. If you don't want to calculate in chess, to learn how to visualize 1, 2, 3, 4, sometimes 5 or more moves per side, you're not going to get better. Your long-term plan will never survive the brutal mid-game realities. You might not even escape the opening.

So you want to design your life five years down the line? That's nice, and spending a little time thinking about it can't hurt. But obsessing over it is nothing if not a fool's errand. You've got your long-term plan, but you wake up hungover every four days, working out only to makeup for the weekend. Nothing builds, nothing compounds. You lay in bed for two hours instead of expanding your mind, painting, going on a walk with a friend. You watch the latest show out of pure passivity, use Instagram as a distraction from a job you don't really care about.

Your long-term plan remains at a safe distance. The issue is you're not actually approaching it. Your plan at age 30 looks retrospectively ominous in its similarity to your plan at 25.

So sleep (a lot, often), eat well (most meals, most days), find someone to workout with you, get outside, think deeply, find your artistic outlets and spend meaningful time with friends. That's the full list of things we 100% know are good for us, so do them.

Focus on your short-terms and stop fantasizing about your long-term. Watch your habits push you towards your long-term goals instead of expecting your long-term goal to erase your habits. Because habits laugh in the face of plans.

Or become an undercurrent for something way beyond what you drew up.