People often wonder why they haven’t caught their “break” yet. They’re waiting for that moment when they’ll hit it big and everything will be like they dreamed.

I wanted to give a brief look at why it’s not some random occurrence. Breaks don’t just come along and say, “whelp, I guess it’s Tommy’s turn today!”

I’ll share some of my successes and failures so you can understand more about how the specific roads I chose led to any breaks that I got. I’ll also talk about the other roads I could have chosen, which would have clearly led to different outcomes.

Let’s look back to high school. When I was in high school I didn’t underst...