Decade 3: 21 to 30
This post is part of a multipart series. I recommend first reading Part 1 and Part 2.
(Yesterday, the Penalty Lap opened, and I enjoyed a glorious lap before writing this post.)
Despite the somewhat jocky anecdotes from decades 1 and 2, I'm a nerd. I suppose most university professors would say that. I followed the rules in high school and college, got good grades, and tread what I thought was a linear path. I went to Wharton, majored in finance, then took a job trading mortgage-backed securities. I wore Brooks Brothers suits for client meetings and Polos with khakis otherwise. I enjoyed the bond job. The intensity felt like a sporting event. I kept up with the more experienced guys because I stayed calm when the markets moved. It was fun; I was learning and making good money. Executing $50 million trades felt like a big deal. I lived in Mill Valley, CA and worked Wall Street hours: 4:30 a.m. to 2:00 p.m.
The truth is, I didn't really major in finance. I majored in rowing with a minor in finance. Rowing was in my blood, and I wasn't ready to let it go. Market hours allowed me to coach a high school crew in the city. We were a ragtag crew of misfits. Kids unable to find space in other sports turned up at the boathouse to give it a try. They had no idea what winning was. I had no idea what not winning was. That's not to say I had no experience with losing. I lost plenty. But I had the great fortune to be a part of many winning teams and contribute to winning cultures.
Our shared ignorance of each others' perspective created something magical. I assumed winning boat races was the thing we were doing. They didn't know what we were doing, so winning boat races seemed like a good idea. And so we won some races, and it was fun, and brought a lot of meaning to my early efforts at adulting.
This mix of activities was lovely. But I soon tired of moving other people's money around and wanted more of the meaning that coaching had to offer. So... I quit. I decided to go for it as a collegiate coach. I took a 90% pay cut, moved back to Philly, and started coaching at my alma mater.
This was the first time I did something unexpected. It kindled a sense that, though it's generally a good idea to follow the rules, the best things in life can happen when you break them.