I had a formative experience playing Little League baseball that taught me lessons about life that I’ve used as a programmer and entrepreneur. Little League is a suburban American tradition where little kids get together on Saturdays and play baseball. Parents come to watch them play and cheer for their kids’ teams.

I played in my town’s Little League from the first day I was eligible until the last day I was eligible, but it wasn’t because I was great at baseball. I was actually horrible at baseball. I could barely catch the ball, I definitely couldn’t throw it, and sometimes while swinging the bat, I would accidentally let go and it would hit people.

Overall, it was a really horrible experience and I hated it. I wasn’t motivated to even try, because I was so bad. I really wanted to quit. But my parents wouldn’t let me quit. “We aren’t raising a quitter for a son,” they said. Instead, they gave me something to aim for: if I hit a home run, they would give me $100.

I got it in my head that I wanted this $100 more than anything. Things started to change. I would go to baseball games and actually try to hit the ball. Don’t get me wrong, I didn’t get better over night, but I managed to slowly improve.

Near the end of my Little League career, I still hadn’t hit the home run and I only had a few chances left. This has to be it, I thought. I get up to bat. The pitcher throws the ball. I close my eyes and swing the bat as hard as I possibly can.

Crack. I make contact and the ball goes flying. I look up and the ball is sailing towards that fence. Closer and closer every second, I can feel that it’s going to go over.

But it doesn’t. It falls just short of the fence. No home run once again.

I look up and at this moment realize that the entire time this was happening, I never started running. All these people, my parents, my coach, my teamates, are behind me screaming at the top of their lungs, wanting me to run. Go! Go! Go! I start running.

Needless to say, I was out before I even hit first base. And I never got the $100, but the experience informed my principle philosophy.

Among the lessons:

  • Swing for the fences, always. I think having a broad vision is super important for equipping yourself for major success down the road. Developers have this tendency to stick with what they know. A big goal forces us to reframe our thinking.
  • Set reasonable goals, too. I didn’t really do this consciously with baseball, but it came naturally. Before I could hit a home run I needed to hit singles, or just make contact with the ball. My open source work, such as the Breakfast Serial helps me set incremental goals toward making it the best Python library for Arduino.
  • You suck… and that’s totally fine. It’s totally fine to be bad at things. You can’t be good at everything and being bad can help you gain a new perspective. For example, I started Hacker League even though I’d never won a hackathon. I focused on things more important than sponsorship and who won because I learned their value first hand, and we ended up better off for it.

I’m still not a great baseball player. I’m not even a great programmer, but I’m getting better by following the lessons above. These days, when I hit the proverbial ball, you’d better believe I’m running as fast as I can.

You can see a video of a talk about my principle philosophy, from which this story was taken, embedded below:

Swift is a developer evangelist at SendGrid who is based out of NYC. He is one of the founders of Hacker League and tweets as @SwiftAlphaOne. Follow him there and check him out at http://theycallmeswift.com.