Over the last few years, I’ve gotten (back) into NASCAR. What started as a COVID hobby when there were few other live sporting events on television has turned into true-blue fandom. I have teams I like and dislike, I’ve been to a couple races, I even have opinions about drivers not yet in the Cup Series. 

NASCAR races are long – usually a few hundred miles / laps, depending on the track. In many races, it’s relatively difficult to pass due to a combination of the track and how the cars perform with other cars around them. About halfway through races like this, it becomes pretty clear which drivers have the best chance to win, and who might not. When there’s a break in the action because of a caution flag, drivers typically come to pit road to get new tires and refuel. Depending on the track and point in the race, there’s usually a clearly dominant strategy – four tires, two tires, no tires and just fuel, or skipping pit road entirely to advance position. On some of those pit stops, a team that’s in the middle of the pack will decide to do something that’s obviously risky, that varies from what the leading cars do. It’ll stand out – that car will suddenly be up front in the near-term. In order for the gamble to work out well for them, a bunch of other events will need to happen – maybe some quick additional caution flags in succession, a large accident, or a change in the weather. The expected value of the decision may be slightly negative – but the difference between the 20th place finish the driver was headed to and a 24th place finish if the strategy doesn’t work out is a risk worth taking, for the opportunity to land a top five or a victory. 

The common commentary for the odd strategy decision made by the mid-pack driver? “If you follow the leader, you follow the leader.” Said another way – if you make the same decisions as the cars in front of you, you’ll just stay behind them. If you’re in 3rd place, that might be a good decision. But if you’re in 20th, you have much less to lose.

Because I’m often multi-tasking during NASCAR races at home by catching up on work, this saying permeated my thinking on my long-term career plan. If your boss is routinely taking Saturday AM phone calls with you, and you stay with your company, you’ve got a lot of Saturday AM phone calls in your future. If your company is in a city that you don’t want to live in, but you’re really great at your job, you’ve got a promising future of being a great employee living somewhere you hate lined up. 

A few months ago, I had the realization I was turning 35 in 2023, and that felt old to me in a way that other milestones haven’t. Maybe it was the gray hair that’s cropping up around my temples or that most of my friends have started families already. After one too many walks in the cold to a delayed, crowded Orange Line train, I muttered to myself, “I’m not going to living in fucking Boston on my 35th birthday.” 

Our movers arrive in less than two weeks. We’ll see how this strategy works, but it’s certainly different than the one I showed up to the race with.