The Web – Winning

People just don’t understand how obsessed I am with winning.
– Kobe Bryant

I almost always win.

I married my high school crush, when other boys in her peer group had tried and failed. I was recognized and promoted over my peers at my summer job, despite being one of the youngest employees. I got into the schools I applied to, with the degree programs I wanted, with honors and scholarships. I got the grades I wanted, and the internships I wanted, and I did well in those positions. I’ve never interviewed for a job and failed to get an offer. I won contests, prizes, competitions.

My divorce at the beginning of this year was the first time I really, truly failed at something I had tried hard to do.

This is probably the definition of a first-world problem, but it is a problem. I am terrified of losing.

My conception – and others’ – of myself as a capital-w Winner means I don’t take the kinds of risks I should. I don’t tend to start things I think there is a good chance of failing. Obviously this is a problem – many of the things I need to do to get what I want out of life have a very high chance of failure (such as picking up women), and only through trying them many, many times is success remotely likely.

So – this is a strand in the web. If I wasn’t so attached to this image of Agon as a competent, skilled, successful person who gets everything done smoothly the first try, it would be much easier to take risks. I’d be more likely to put myself in situations where I’m likely to look like an idiot, situations where I will lose out to other people or get unlucky or just plain not be good enough to meet my goal.

I almost always win, and since I’m not king of the world yet, this can only be because I’m not challenging myself enough. So my desire to keep always winning is a strand in the web – I need to redefine how I think about challenge and failure, and try harder things. Until I’m putting in my full effort and still failing a significant portion of the time, I’m not pushing to my full potential.