Based on your book, you seem to have a gift for shrugging off failure.
I’ve learned to cope with the idea that failure is a constant in most people’s lives. Like once, as I describe in the book, I bought a dirt bike on eBay and wanted the immediate gratification of riding it around New York City. But it never worked out. I rode it for a total of 45 seconds before I got a ticket. That’s emblematic of my life in general, I think. In the book, I try to show readers how to let failures wash over you and live with them in a positive way. Like, don’t board up your windows and shit on yourself. Don’t isolate yourself from the rest of the world.
Have your failures, by and large, been stepping-stones to bigger and better things?
No way. I think that’s a trope perpetuated by successful people and self-help books. You never hear stories about people who keep failing, failing, and failing, because there’s usually not a clear, positive message. But—even if you never succeed in a big way—when you fail and hit bottom, that’s when you really change for the better. People who struggle and fail all the time, they usually don’t have a sappy, end-of-the-rainbow tale, but they’ve learned how to deal and move on. And that’s valuable. It sort of strengthens you for future failures.
What’s a failure or setback you’ve had to deal with recently?
I have a really unhealthy relationship with my kid now because of this book. I have to be like, “Don’t take it too seriously!” I want him to feel free to make a few mistakes, but it’s not like I want him to fuck up all the time.
From Bad to Worse
A sampling of whiffs from Benjamin’s new book, Failure Is an Option.
At a park, Benjamin chats up another parent—as his newborn chews on a dog turd.
He watches as a neighbor’s house gets robbed, tells the burglars where he lives, then gets robbed a week later.
He hires two gay escorts to perform with him in a live comedy routine, basically gets scammed out of $500, and earns $10 for performing.
This essay is part of our Art of the Fail series.