Do you love to win more than you hate to lose?

That question was on the back of a shirt one of my students was wearing Monday. We were playing Ultimate Football, which is Ultimate Frisbee with a football, as part of an offseason tackle football conditioning program. He was on the opposing team, and I kept seeing it in front of me. Finally, I asked.

“What is the right answer to that question, on the back of your shirt?”

He looked confused for a second, like the answer was obvious, and then answered.

“Oh, well we think it’s loving to win.”

He said “we think” because the shirt was a product of a third party organization, a group we have teamed up with to offer tackle football for our students. I trust their philosophical approach to competition.

Is it an easy question to answer?

I first starting dwelling on this topic in high school, and I reached the opposite conclusion. Framed in a loss aversion context, I could see how it’s supposed to encourage risk-taking and a no-fear approach to competition. I support that, if that’s the case, but we were in the middle of a non-stop up-and-down game, so we didn’t have time to dig deeper into the philosophy behind it.

“I disagree”, I said. “I expect to win, so I’m disappointed when I lose, and winning doesn’t feel particularly special most of the time.” Or something like that.

“Okay, you convinced me,” he said, verbatim. The competition resumed.

I’m still thinking about it, though. The “love to win” argument could also be helpful in a losing atmosphere, when you’re trying to build momentum and buy-in. Is there a right answer?

My fall sport in high school was volleyball. My school didn’t have football, and though basketball was our primary sport, the best male athletes played volleyball, too. Senior year, my best friend, who was also a starting outside hitter, moved out of state. Basically my entire competitive career, going back to seventh grade, I had pictured us playing together, winning everything together our senior year. After he left, I became despondent. Or, what’s a word like “despondent”, but with more teenage angst and anger? I was still going through the motions, but I withdrew mentally and emotionally, started resumed getting into trouble at school, and was just generally disconnected. Volleyball season was going along as expected, nothing stood out.

Then we lost. To our rivals. Badly.

I don’t remember much from the game, but I remember how I reacted. I stayed up most of the night, sitting on the floor in my basement, game-planning everything we needed to do differently in order to beat them the next time. I came up with new rotations, new practice drills, everything. Losing woke me up.

We had a first-year coach, and she was mainly there to keep the team intact. A favor to the school. When I showed up the next day at practice, with handfuls of scribbled notes and strategies, she followed my lead. Looking back, that moment was the start of my coaching career. After the season, she even addressed it, and specifically told me I had become a different person after that loss. Our rivals beat us again in the rematch, had the first undefeated regular season in conference history, then lost to us in the conference championship game. It’s one of the few things that went right my senior year, and I treasure that memory.

In college, I noticed I had a similar approach to academics. I would coast in my classes, putting in the minimum work to reach my standards, grade-wise, until I hit a speed bump. A failed test, a blown assignment — a loss — and all of a sudden it was game on. I lost many of those wars, but I still couldn’t fully focus on each battle until I took an L first. My approach to learning has matured since then, thankfully.

I’ve resisted circling back to basketball long enough. In high school, I practiced a lot, like a lot a lot, on my own, and I started to excel at one-on-one. I didn’t lose for years, in fact, highlighted by winning a one-on-one tournament on a cruise ship one summer. You’re starting to resent me at this point, I imagine, because this is considered bragging, but as OBJ would say, “That’s just real rap“. At least you can take a break from resenting me for being a feminist… ha, yes I just linked to my own blog. But seriously, don’t worry about me, I’m a well-adjusted former one-on-one cruise ship champ. I also won some sort of blind date/game show contest on that trip, but that’s a different story, and one I don’t remember as vividly, sorry!

Here’s the thing. During my winning streak, I started to intentionally increase the level of difficulty. I wouldn’t take the free layup after an airball or steal. I would blow by someone, then wait for them to catch up to take a tough fade-away or cross them even harder. If it was the game-winning basket, I would go even farther out of my way to make it a significant achievement. Why?

If it wasn’t thrill-seeking, it was definitely upping the ante. It wasn’t enough of a rush to simply score, or win, I needed more of a challenge. This led to some bad habits, admittedly, and my five-on-five ability may have been adversely affected. Being good at one-on-one is much different from being good at full court fives, for the record. The point is, winning wasn’t enough, but I wasn’t terrified of losing, either. The quality and closeness of competition is what mattered, because that amplified the highs and the lows. I wanted to make great plays in tight games, I wanted to be pushed to my limits. If I lost a game because I hadn’t taken the easy points, so be it. I knew losing would motivate me more than any other outcome. I hate losing.

Just over a week ago, I was at a going-away party for a family from our school, and I lost a close ping pong game to one of my students. I have thought about that loss, on average, more than once a day since then. Don’t laugh at me, I could write a whole blog post about it at this point! If I had won, though? Not a second thought.

All of this seems consistent with what I’ve seen and read from professional athletes and competitors. When an undefeated team loses just before the postseason begins, you already know the narrative, right? It’s treated as a positive! Winning had made them complacent, losing will make them refocus. Many athletes are surprised when they reach the top of the mountain and realize it doesn’t feel as good as they thought it would. The fight, the adversity, the climb, a previous setback and redemption, was more enjoyable than the peak. The more success one has, the more that becomes true, I suspect. Maybe that’s why Michael Jordan quit basketball after three straight championships and tried his hand at baseball. If he just loved winning, why would he choose to end that streak? Maybe he had a gambling addiction and was suspended by David Stern. That theory could support the “love to win” side of the equation, in that winning at basketball wasn’t enough, he had to win at golf, and cards, and everything else, too. Except being the owner of the Hornets, I suppose.

It’s worth noting that the best competitors and winners in history are typically not pleasant people. This is a big reason why I consider being described as “nice” as an insult. True competitors are not fun to compete against, and often not fun to be teammates with, either. Their obsession with winning (or is it an obsession with not losing?) comes above everything else, including your feelings. If someone or something is holding them back, they can be ruthless in calling it out. Jordan is such a legend because he could flip a switch and turn it off in the commercials, for the media and public, and that’s why people were comfortable embracing his greatness. Kobe modeled his Mamba Mentality after Jordan, but he wasn’t as likable. People criticize LeBron for being too likable, not having a killer instinct, but he just goes about it differently. The guy runs the league, and he’s wants to be considered the best ever AND a billionaire. That’s why he spends $1.5M/year on his body, he’s betting on longevity being his ace in the hole.

My tendency to hate losing more than I love winning can manifest as a weakness in my coaching ability. If we are clearly better than an opponent from the start, I find it highly difficult to focus, to maintain my intensity. I start to think about other goals, like getting an end-of-bench player in the game, or experimenting with weird lineups. This can lead to a lack of focus from my team, which can lead to sloppy play, and unsatisfying wins. Great coaches keep the same intensity regardless of score or opponent, and keep the same standards for execution in all situations. I’m working on it.

Back to the Ultimate Football game. Score is tied, two hours in, next point wins. Jump ball to the corner of the end zone, caught over my outstretched fingers. Yeah, that’s gonna leave a mark.

Here’s my final answer. The best feeling is winning a game that you should have lost, and the worst feeling is losing a game that you should have won. One of the signs of a mature competitor is recognizing when “should have” applies. You need to love winning and hate losing to be a great competitor, but if I had to choose one extreme that’s going to lead to me becoming the best version of myself, I would choose never winning over never losing. What about you?

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