Here’s something I’ve realized about myself in the past few months: I am pretty decent at losing. Now, I’m not saying I was born to lose. But I’ve developed a half decent skill in it. I’m talking about losing in the competitive sense, but to be honest, it might be more than that if I stop to think about. When it comes to the competitive side of things, I attribute some of my capacities at losing well to being the youngest in my family. The chances of winning at whatever competitive (or non-competitive) thing you’re doing with two older siblings are slimmer.
Recently, chess has helped me realize I’m good at losing. A new acquaintance mentioned their interest in chess, and I piped up and said I’d be keen to play. Why was I saying that? I haven’t played chess in ages. I lose most of the time. I was saying that because I had something else other than winning at chess in mind.
Happily, I’ve lost many games and gained exposure to new people who like to do new things, in new places. This has led to playing chess in various parks, and even in a cool café in town that hosts a chess night every couple of weeks. The rest of the time, it’s "just" a cool café that I didn’t know about. Now it’s a new favourite place.
Exposure to new experiences isn’t really what I’m after, though; it’s sharing quality time with people I like. Making friends after your 20s can be hard. I think something as benign as being good at losing makes winning at other things, a little easier.
I respect people who are willing to lose again and again, and with grace. This is not so different from an artist who accepts that their work is not as good as they wish it to be. Each attempt gets them closer to their ideal output, but until then, they must face a form of loss.
In writing this, I remembered my first boss, the president of the company from my first real job out of school. We played on an intramural frisbee team. We lost every game we played. At the end of one particularly difficult game, I watched him angrily throw the frisbee at the ground. A simple act like that, sadly, made me see this person in another light. Of course, just because you run a company and are in a leadership position doesn’t mean you can’t have emotions of anger or frustration, but it can still allude to concerns about how that person might react to bigger stakes. 
Nobody likes a sore loser. Not exactly the kindest aphorism. While I’m not talking about being liked, here, I am talking about building relationships. So come on over some time, and crush me at chess, checkers, connect-4, carccassone, catan (or another came that doesn’t start with the letter
C, if you must). We’ll have a good time.
With that said, the person in this anecdote was always kind, patient and good to me. ↩︎