Updated: Jul 25
Back in high school, I was a pretty good tennis player. During my sophomore year, my team won the NJ Group II State Championship and advanced to the Tournament of Champions. In our bid to run it back the next year, we lost a nailbiter one round earlier in Central Jersey Group II Championship.
At that point in my tennis career, I was able to go out on the court and consistently win points. To beat the best opponents I faced, I had to actively beat them—I couldn’t rely on just trying to keep the ball in play. The final outcome of each point was typically determined by someone winning the point, not losing it.
Nowadays, I play a lot less tennis. While I’m not quite washed up, I’m a long way off from my glory days. Yet, when I go out on the court, my brain likes to think I’m as good as I used to be. I still try to control the point and am always looking to hit winners. Sadly, I don’t have the same success that I once had. My game is now riddled with unforced errors.
Rather than winning points, I’m losing them. My opponent isn’t beating me—I’m beating myself. Any wise opponent who faces me these days should realize this. If they do, it becomes clear that to beat me they just need to avoid losing. If they adopt a strategy of keeping the ball in play and avoid making stupid mistakes, I’ll likely be too aggressive and will end up making my own.
While I can’t seem to adopt this strategy in my own tennis game, it’s one that I’ve found immensely helpful in other areas I don't have expertise in. This strategy of playing not to lose is derived from one of my favorite mental models. It’s a relatively simple model, but one that’s incredibly effective—especially in situations where you’re not a professional. Avoid stupidity rather than seeking brilliance. Put another way, rather than trying to win, avoid losing.
Following this model, I’ve found that I’m much more likely to be successful in most aspects of life if I just avoid making stupid mistakes. Unless you're operating at an elite level, playing not to lose can often be the best path to winning. This is true in business, sports, politics, and even war. There is a great quote from a military general who once said, “it's not that good soldiers become veterans. It's that lucky soldiers become veterans, and veterans are good soldiers.”
Putting It to the Test
Charlie Munger, Warren Buffet’s longtime business partner, has long advocated the usefulness of this model. Many years ago, when Munger was the Chairman at Wesco Financial, he wrote the following in a letter to shareholders:
"Wesco continues to try more to profit from always remembering the obvious than from grasping the esoteric. … It is remarkable how much long-term advantage people like us have gotten by trying to be consistently not stupid, instead of trying to be very intelligent. There must be some wisdom in the folk saying, `It’s the strong swimmers who drown.’
In the startup world, the most successful executives are often those who have managed to survive long enough to become good leaders. They focus on just staying alive and figuring things out along the way. By avoiding stupid mistakes, they increase their chances of eluding a final resting place in the startup graveyard.
Back when Paul Graham was running Y Combinator, he once said YC expected about a third of the companies they funded to succeed. Maybe 50% on the optimistic side. With this in mind, PG told a group of founders in a new YC cohort one summer the following:
“If you just avoid dying, you get rich. That sounds like a joke, but it's actually a pretty good description of what happens in a typical startup. It certainly describes what happened in [his startup] Viaweb. We avoided dying till we got rich.”
Charlie Songhurt had another great way of saying this in a recent interview he did on Invest Like the Best. When describing how companies can succeed, he said:
"If you're sort of thinking of history, trying to be as good an Emperor as Augustus would be really difficult, but not being as incompetent as Caligula seems really easy. And so as a practical advice, not making the catastrophic mistakes and just surviving long enough feels like a good strategy."
The more you look, the more examples you'll find of successful founders and companies that follow this approach. If you look back on the career of Jeff Bezos and Bill Gates, they didn't always have an aura of greatness around them. In 1999, Jeff Bezos was working out of a single room office with an Amazon.com logo spray-painted on the wall. Through staying alive, and avoiding stupid mistakes along the way, he was able to set himself up for greatness.
Putting It to Use
While avoiding stupidity sounds pretty straightforward on paper, it’s not always easy to do in the real world. Oftentimes, we don’t realize something is stupid until after we do it. As humans, our stupidity filters get clouded pretty easily. Keeping them clean can be a challenge. To make it easier, you can bring in the mental model of inversion for backup.
Simply put, the model of inversion is thinking about something backward. Rather than thinking about why something will work, you think about what might make it fail. By using inversion you're forced to consider different perspectives. This almost always leads to a better understanding of the situation or problem at hand. Used in tandem, these mental models forge a great weapon to have in your arsenal.
Whenever you find yourself in a situation where you’re not an expert, remember that it’s much easier to avoid stupidity than it is to seek brilliance. Playing not to lose can often set you up to win. Maybe someday I’ll accept that with my tennis game.
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H/T to Farnam Street for introducing me to this mental model a few years back