Playing to Win vs. Playing to Play
If you can accept losing, you can’t win.
It was my final year in high school, and I was at my last ever wrestling tournament, on my back 30 seconds into the first round, about to get pinned and eliminated. Sadly, it looked like my last ever wrestling match would be a resounding loss.
I was never a good wrestler. Each year my coach sends out the all time stats list, and each year I am reminded of my quite underwhelming 7 wins and 19 losses. For some reason, even though I was pretty good in practice, I just wasn’t able to win matches.
However, on my back facing the possibility of losing my last wrestling match ever, something in my head clicked. I decided that no matter what it took, I wasn’t going to lose my last match. I survived the next minute and a half on my back, and turned it around over the next four minutes, getting ahead on points and then pinning my opponent near the end of the match. I won all my other matches, and placed third in the tournament.
In our society we have this idea that as long as kids try their best, the outcomes don’t matter. This wrestling match was my first exposure to the idea that making a decision to win, regardless of the consequences, can be the difference between winning and losing.
Sadly, this lesson didn’t last long. When the tournament was over, I went back to making the same kind of mistakes. I thought that if I committed to something and tried my hardest, that I was doing all I could, and the final results didn’t matter that much.
I made the mistake on the crew team. After walking onto one of the most elite crew teams in the world, I never made the jump to say that I needed to be one of the best rowers in the world. I went to practice, tried my hardest, and was content at participating and happy to be there. I never looked around at the Olympians on the team and realized that I was losing. I wasn’t supposed to be coming to practice and doing my best, I was supposed to be improving myself until I was the best.
I remember one time, being very emotionally conflicted after losing a tough race. Part of me thought that we tried our best, and that the results didn’t matter. However, there was another part of me that was disgusted that I could put such a huge amount of effort into rowing and be okay with losing. It was the part of me that knew intuitively that the purpose of rowing wasn’t to row, it was to win. And I wasn’t winning.
I made the same mistake with launching The Comical, a comedy magazine that I launched in NYC with two friends. My partners and I were trying our hardest, and losing left and right. We never sat down and realized how badly we were losing, and figured out a way to make it possible for us to win. We just kept working, and kept losing.
The reason that it was tough for me to realize what now seems obvious in hindsight is that trying my best and working hard was generally sufficient to accomplish most things. If I hadn’t had some major failures, I would never have realized that trying my best is just not good enough.
When you’re playing to play, you try your best. When you’re playing to win, trying your best is just the beginning. Firstly, “your best” is a highly variable amount of effort. A person who is playing to win and is losing will put in much more work than one who is playing to play. Next, if the effort isn’t working, they person playing to win will be much less accepting of the situation, and will make changes that the other won’t in order to ensure success.
I have a tough time with this. It has been too many years having this bad idea reinforced. After putting a huge amount of work into something that doesn’t pan out, it’s tough not to feel some sort of accomplishment. It’s something I’m working on.
Taking this approach towards anything is very emotionally taxing. You can probably only have one or two things at a time where you make the decision that you will win, no matter what it takes. However, if you’re doing something important enough, you can’t afford to lose. You have to play to win.
About two years ago I launched a fashion website called Am I Stylin, where users could post pictures of their outfits, and then other people would vote to see who had the best outfits. I put a huge amount of effort into launching the site, but when things were tough and the site didn’t gain any traction at the beginning, I gave up. I had an amazing backup plan at my full time job, and losing was easy. I was playing the game of entrepreneurship, but I wasn’t playing to win.
Right now, with Memoir Place, I am playing to win. I may have temporary failures and setbacks, but I will overcome them. By quitting my job and closing off all other options, I have committed 100% to winning at all costs. I have no backup plan. It’s success of bankruptcy. That’s why I’ll win.