Playing the end game

Josh Waitzkin, author of The Art of Learning and the inspiration for Searching for Bobby Fisher, was one of the best chess players of his time. He was an International Master by 16, outpacing people double and triple his age.

How did he do it? Why was he such an outlier? Well, you can read the book to find out.

But here’s the TL;DR version: He was taught chess backwards.

Instead of learning the different opening moves, how to trap your opponent in the fewest turns — Josh was taught the end game first, just a king and a pawn. He mastered the end game, worked backwards and learned the starting moves last. This allowed him to thrive in chaos. When the board didn’t go according to plan, when none of his plays worked — he remembered the end game and like a north star, it guided him through the chaos while everyone else faltered because the game didn’t follow their well-defined move sets.

Unorthodox. Thriving in chaos. Focused on the end game. Josh and I are basically kindred spirits (if you’re reading this Josh, hit me up!).

I wrote a while back about why young-ish folks should have values. I’ve grown to learn that along with values — the most well-respected people also have principles that they live by (what those are, how to find them, I won’t cover here. Just that it’s important to have them.)

Playing the end game is one of my core principles. At work, with my friends and family, but most importantly — with life as a whole. As Christopher Walken famously said,

None of us are getting out of here alive, so please stop treating yourself like an afterthought.

Brace yourself friend, we’re gonna get deeeeeeep about death.

At best, we’ll get a heads up about when we’re going to kick the bucket. You get diagnosed with a disease and a six month countdown, or you’re hospitalized due to… whatever, but you’re still conscious enough to function.

At worst, (and for the large majority) — the end is abrupt, unseen and without warning. Hit by a car, a random aneurism, or a thousand other ways. And unfortunately, there are no redoes, no command + shift + z in real life.

Some would say I spend a concerning amount of time contemplating death. But the guarantee and absoluteness of it makes prioritizing life a lot easier — the exercise of negative imagery (taken from the Stoics) removes the typical emotional reactions caused by life’s annoyances; people cutting you off, someone towing your car, -40 degree weather. Those things become irrelevant.

Because, does any of that matter if you weren’t here tomorrow? How badly would you wish for another -40 degree day if you knew tomorrow was your last? Or that argument you got into with your Dad, how much would you regret if that was your final conversation?

If you genuinely gave it a thought, I think you’d arrive to a place where few things would rile you up, make you mad or frustrated. You’d be more focused and intentional with your time because you’ve cut out all the bullshit. It doesn’t matter who’s right or wrong when that random person brushes you while walking down the street, you just move the hell on.

It can sound morbid (we are talking about death after all). And maybe you’re saying “Eva, you shouldn’t think about that stuff” like many of my friends would. But I think remembering death is an unfair advantage in life — my superpower if I had one (clearly, all the good ones were taken). For entertainment and reader engagement purposes, try to think about death for 15 seconds. I mean really think about what it means if tomorrow goes dark. No growing up or growing old, no friends or family, no redoes or will do’s. It’s scary as shit right?

Now, use that fear to do something you’ve always wanted but was too afraid to, cause whatever it is — it’s probably not as scary as what you just imagined.

In a less dramatic fashion, Jeff Bezos’s regret minimization theory is a similar line of thought without the whole death thing. I’d recommend checking it out if the morbidness of this is bothering you.

Now that you’re mildly depressed and/or traumatized, here’s what my end game looks like. On my deathbed, hopefully I (or someone) can say that…

  • I spent the majority of my time on something that positively impacted people’s lives. That actually made (and hopefully continues to make) a meaningful, measurable difference.
  • The scale of that impact was in the hundreds of thousands, if not millions.
  • I had a small group of friends that would bail me out of jail, if ever necessary. And then still be my friends.
  • I had great individual relationships with everyone in my family.
  • I had seen more of the world than I hadn’t.
  • My proudest possessions were certain experiences and stories instead of physical things.
  • I did 1000 things that scared me.

That’s my criteria of my life well lived, my definition of winning at this game called life. Of course, yours is probably very different but knowing what’s in your criteria and actually having a criteria — that’s the only important part. Otherwise, aren’t we just following someone else’s definition of winning? Or going through the motions of what we “should” be doing?

Once you have your set of criteria, there’s an easy litmus test to see if you’re living integrally to it — look at your calendar for the past month. Where did you spend most of your time? Your money? Does it align with your end game?

If not, it might be a good time to re-evaluate why. Then ask yourself — what are you going to do about it?

Moonshots @insidePN. Growth Alumna @OpenCareHQ. Member of @Growthhackers. Lifelong Student. Collector of Experiences. Can be seen writing on a good day.

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