The political strategist explains how detours and shortcomings can get you where you want to go. I stood up to authority.
At 12 I was an assistant softball coach. Telling my mom why I had to bench my sister taught me I could make tough decisions for the greater good.
I was fiscally irresponsible.
In my 20s, I'd blow all my money on a Eurail pass and return broke but happy. I learned the only way to save was to put my credit cards in the freezer and pour water over them.
I ran my mouth.
My mom once bought me a cassette player so I'd shut up and listen to some music. If she'd lived to see me on TV, she'd see that worked.
In 2000 I achieved my dream of managing a presidential campaign—Al Gore's. Though I really believed he could make a difference, the job was stressful and thankless. A few months after we lost, I found a new calling as a commentator and critic. Now I can give my opinion without taking a poll.