Sometimes You Have to Lose a Game to Know If It’s Worth Playing

We are all playing games right now.

I’m playing Write-The-Best-Blog-Post-Possible-Before-Midnight. You may be playing Get-That-Girl-To-Like-Me, Impress-The-Boss, or Make-More-Money-Than-My-Friends. Odds are, you are playing multiple games at once. That’s fine. Your whole childhood prepared you for this.

Whatever you’re doing, you’re engaged in a

Game, n. “A form of competitive activity or sport played according to rules.”

In Write-The-Best-Blog-Post-Possible-Before-Midnight, I have to avoid making grammar mistakes. I will probably lose this game, but I play anyway. It’s competitive in that I am competing with my own past blog posts as well as all of the cat videos you could be watching instead of reading this.

See what I mean?

If all of life is games, a pretty important question is this: how do we know if our games are worth playing?

I’ve only been playing games for 21 years, so that makes me a young whippersnapper of a player. That said, today I noticed something about the meta-game.

If you are winning a game, you may never know if it’s actually worth playing.

Case in point: when I was in high school, I made really good grades. I was one of those monstrosities you call a “model student.” I was playing Make-The-Best-Grades-And-Please-Everyone, and I was winning by a good stretch.

Then came Statistics.

I believe this was the first class where I made C’s and D’s. That took me a while to get used to. This was supposed to be the easy class.

Meanwhile, some of my classmates excelled in AP Calculus. Their GPAs went up that year, whereas mind fell in accordance with my Stats grades.

First, let me just say that they totally deserved to beat me. They worked their tails off, and as pointless as I think school is now, I still respect them for putting in the effort.

That said, this loss in Make-The-Best-Grades-And-Please-Everyone was just one place where losing the game gave me the perspective to question the game itself. The people who were winning the game mirrored back to me all of the effort and sacrifice required to be a top scholarship-winning, GPA-perfecting, college-attractive student.

Beyond just grades, that process required self-curation, conformity, and a resume-building mindset that gave me the creeps. And I had already done it to an extent.

My most powerful experience of a competitor mirroring my game back at me came during college scholarship interviews. My college scholarship roundtable interview at one school brought me face to face with this in a co-interviewee, who at age 18 proudly spoke of her civic awareness and well-roundedness and desire to be a president and save the children, etc. etc.

She may well have meant it, but it struck me all as grasping and inauthentic at the time– enough that anyone in that room could have seen the pandering. She probably got the scholarship, though. That’s what sells/wins in the college scholarship game. That’s the strategy I would have had to play to win, and it would have been wrong.

That whole process didn’t just just erode my faith in the Make-The-Best-Grades-And-Please-Everyone game – it eroded my faith in the Look-Good-For-Colleges game. As many of you know, this exposure to the high-achiever end of college culture fed into my decision to skip the hoop-jumping higher education system completely.

Don’t get me wrong. A lot of people decide a game isn’t worth playing because they’re bitter about losing or not being #1. This is not what I’m talking about, though I’m sure I have some weird unresolved bitterness about grades and scholarships in my messed-up subconscious mind. Coming in second, third, or even last is no reason not to try a game worth playing, like Life, or Raising-Your-Children, Creating-Value, Making-The-World-Better, or Not-Being-A-Complete-Jerk. The need to be seen as great – or not play at all – stunts the growth of everything.

My point is not that losing should be informing your decisions about which games are worth playing. Your desire to “beat” others should not certainly not be informing your decisions.

My point is that winning alone is not a sufficient reason to play a game. And sometimes that’s exactly why we find ourselves playing the games that make up a big part of our lives.

If I had continued to be the kind of model student that winning the Make-The-Best-Grades-And-Please-Everyone game, I don’t doubt that some school would have given me much more free money to spend four years of my life taking classes and making more grades and playing the same game. I would have accepted the money, probably. I also don’t doubt that it would have been terrible for me, my emotional development, my intellectual development, and my moral development. The way I was going at the time, I genuinely think I would have been a corrupted person if I had chosen to go to college at that juncture.

Losing was the best thing that happened to me.

What games are you winning right now? Be prepared for someone to come along who will play them better than you, but welcome them when they come. They will show you exactly whether you want to compete with them or find a new game.

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James Walpole

James Walpole is a writer, startup marketer, and perpetual apprentice. You're reading his blog right now, and he really appreciates it. Don't let it go to his head, though.

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