Getting Comfortable With Failure

I just got back from a Meetup of budding entrepreneurs. A couple of them volunteered for the “hot seat” at our meeting: they spent 3-5 minutes talking about their business idea, and asking for any and all advice from the rest of us on how to move forward. 

Each of these businesspeople had an idea, a great and powerful idea. But they expressed fear about making a commitment to bring that idea to life. They were afraid they weren’t ready. They were afraid to try something and find that it didn’t work. They were afraid that trying something and finding that it doesn’t work reflects back on them and means that they are a failure. 

They didn’t say it exactly like that, but I recognized those fears because I have them, too, every single day.

The War of Art, which I’ve been listening to as an audiobook, has been helping me recognize those fears so that I can face them. It’s been especially good at teaching me that trying something and having it completely and utterly fail does not mean that I am a failure. It just means that I need to try a lot of things before I find the thing that doesn’t fail. 

So what does this have to do with Bob Dylan?

Well, I’ve noticed over years of being his fan that Bob Dylan’s music is not just loved and enjoyed. Bob Dylan himself is revered as an unassailable genius. Inspired. 

“This is an artist whose working process has been as private as his personal life,” said a New York Times article this past Sunday. Maybe for this reason, I find that lovers of Dylan’s music always talk about Dylan like he’s someone who doesn’t have to work to produce the great music he’s created over the decades. It just comes out. 

Internalizing that notion has been dangerous to my survival. Because over the years it’s made me feel like if I don’t “get it right” right away, I shouldn’t bother at all. This despite the fact that another writer a lot of people admire, Ernest Hemingway, once said,

Don’t get discouraged because there’s a lot of mechanical work to writing. There is, and you can’t get out of it. I rewrote the first part of A Farewell to Arms at least fifty times. You’ve got to work it over. The first draft of anything is shit.

The Times article provides evidence that the Hemingway quote is as true for Bob Dylan as it is for any of us.

Dozens of rewrites track the evolution of even minor songs like “Dignity,” which went through more than 40 pages of changes but was still cut from the 1989 album ‘Oh Mercy.’

I had to read that line twice.

Bob Dylan worked through more than 40 pages of changes to a single song. And then he cut the song from the album. 

Rewrites and failures happen with the trying. Trying and failing go together. Not trying and not failing just mean that you never get to succeed, either. That is what I’m realizing. Some days when I feel like I’ve really messed up or I’m never going to figure anything out, that realization provides no comfort. Trying just feels too hard and the potential for success doesn’t feel worth it. 

But today, as I watched other budding entrepreneurs with potentially life-changing ideas peer wide-eyed over the edge, look back up at the group around the table, and say, “Do you really expect me to jump off this thing??” it gives me a lot of comfort.

Jumping feels scary and of course it does! If you jump off a cliff, you will probably land on your face. Until the time that you jump and you don’t land on your face. I’m still waiting for that time, let me tell you. But! 

The difference between Bob Dylan and many other potentially great songwriters and performers is that Dylan doesn’t stop at “potential,” and he never has. That may even be the secret reason people are so fascinated with him, although the mysteriousness probably also doesn’t hurt. But he doesn’t let the second-guessing stop him before he can get started. That makes him different. 

Although may I just point out: Dylan has landed on his face MANY times, sometimes privately, sometimes in front of everyone. There was the example of the song above. There was Self Portrait.

And I myself witnessed an instance of Bob Dylan face-flatness. It was the time my friends and I saw him perform three summers ago at Jones Beach. He sounded so bad that we left early. On the way out my friend Daniel made the comment you see below on this Instagram photo. 



Revered genius Bob Dylan fails on a consistent basis. I guess I can, too. 

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