When they offered Conan O’Brien the Late Night Show, he wasn’t going to take it. He was living in a (self-described) paltry apartment, writing for The Simpsons, and overall enjoying a simple, rewarding life.
He called his friend Robert Smigel.
They agreed getting out of the writer’s room and into the performing business was exciting. They also agreed this would be a terrible way to do it.
Conan was still in his 20s. If he took the job he’d most likely be slaughtered by the critics. Then, he’d eventually end up back in a writer’s room – the only thing he really knew how to do – with this very public failure on his resume.
Smigel’s wife was in the background and overheard the conversation. She said, “but what does he have to lose?”
Conan semi-overheard and asked, “what did she just say?” Smigel repeated her question to him.
Conan took another look around the apartment. He thought about the work he already knew he could do. He responded, “I guess… nothing? Good point. What do I have to lose?”
And so he took the job.
Once we know what we can’t lose, like our talents and skills, it can make it easier to bet on what we might have to gain – if we just take the risk of putting ourselves out there.
Opportunity is scary. It’s good to remember what we can’t lose.
h/t this podcast episode – it’s awesome, “Conan O’Brien & Jeff Ross Look Back.” They reflect on the beginnings of their careers and I found it fascinating and inspiring.