Underdogs Forever

Sitting at the intersection of culture, sports, and the Substack-adjacent space (although he appears to be using Kit), Tom Brady made headlines this week by launching a newsletter.

He is calling the newsletter 199, a callback to his position as the 199th overall pick in the 2000 NFL Draft. Even a non-football fan like moi can tell that this is not a particularly great draft number. But isn’t it interesting that 25 years later, this not-great draft pick number still holds enough significance to Brady that he named one of his first major non-football projects after it?

It made me think: I’ve noticed that folks often want to be seen by other people as champions, but they often like to think of themselves as underdogs. He didn’t call the newsletter 7 after his 7 Super Bowl wins, he called it 199 after a time when he was, arguably, quite an underdog.

I think this is because when you think of yourself as an underdog, even if most of your world thinks you are the GOAT, you give yourself permission to be scrappy, to try new things, to throw things against the wall and see what sticks.

Telling yourself you are an under-estimated underdog seems to be one path to taking the pressure off trying something new. Even if you’re just starting an online newsletter. And even if you’re Tom Brady!

-Molly Beck