When Your Shot Arrives, Respond Like This

I recently learned the story of Billy Oppenheimer, who is now a main research assistant and key team member for writer Ryan Holiday, of Daily Stoic fame.

But a couple years ago, Billy was just a ski instructor and recent college graduate who wanted to be a writer. After becoming interested in Holiday’s books (Obstacle Is the Way, Perennial Seller, and others), he sent Ryan an email thanking him for his work, and offered to help out on any projects Ryan might have for him. He sent the email and moved on with his life.

Then Ryan wrote back.

Billy tells the whole story in a great interview on YouTube, including sharing the exact email that he sent to Ryan. But the email is not really what set him on the path to becoming a full-time team member for a famous writer and philosopher. It’s how he responded that mattered most.

When Holiday sent Billy a project, he delivered. Same for the next project, and the next and the next. (Holiday paid Billy for each project.) When Holiday asked for Billy to take on more responsibility, he said yes. Every time.

Billy overdelivered.

Comedian and writer Judd Apatow tells a story about his first job as a comedy writer. After putting himself in the vicinity of comedians as a teenager, he got a call from one of his heroes, Garry Shandling, asking if he wanted to write jokes for Shandling for the Grammys.

Instead of writing 20 jokes, Apatow stayed up all night and wrote 100. He faxed them to Shandling the next morning. Shandling ended up inviting Apatow to come to New York and be there for rehearsals and the show, and Apatow worked with Shandling for years after that before developing his own writing career.

When your shot comes, you must do the same. You must overdeliver.

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