Joel Englander ‏@JoelEnglander: How do you get comfortable with failure?


Let’s define failure: you pick a goal, take a number of steps to make that goal, and somehow the goal doesn’t happen. And it feels really really bad.

Is that failure?

No, not at all.

Failure is when you then say, “Shit! I failed.”

Now it’s a failure.

When I was in my 20s I practically gave my life to write and publish a novel. I wrote 3 novels of about 400 pages each. I wrote a novella of about 150 pages. I wrote dozens and dozens of short stories. I wrote comic book scripts. I wrote screenplays. I planned documentaries. I shot TV pilots. It is so boring to spend 8 hours a day typing something that will never ever see the light of day. I was thrown out of graduate school. I took crappy jobs that would give me time to write. I gave up spending time with my girlfriend(s). Embarassingly (to all my friends), I kept calling myself “a writer”.

And I never got a novel published. To this day. I kept sending stuff out to agents, literary magazines, publishers. I would take classes on writing. I would read encyclopedias on literary criticism. I would read every writer I could to see what they were doing right that I wasn’t. I would think to myself over and over, “Damn, I can do it better than this guy.”

But I didn’t. I wasn’t. I failed.

So finally I gave up. After five years of writing 3000 words a day, I took a job at HBO, I made some creative websites that I’m proud of, I started a company, I sold it, I lost all the money I made, I bought a penthouse apartment in NYC, I totally lost it, I built and sold other companies. I built and failed at other companies. Meaning: all the money disappeared. I started writing about finance. Very different from writing novels. Or not. I wrote some boring books on finance. I started angel investing. I ran a fund of hedge funds. I did lots of things.

I never got comfortable with failing. It’s like putting on clothes when you are wet. Sometimes you have to twist and squirm a little to get everything on. The same thing with life. Most of the time you are all wet. But you have to put your clothes on every day and do the things you were meant to do. The things that put a roof over your head, feed your family, live your life, love your life. Eventually you get your clothes on so you aren’t naked.

Now I write about all the times I tried and it didn’t work out. I write about everything I did. I don’t hold anything back.

And every now and then I write a post that totally sucks. Every now and then I still have many ideas that don’t work out. And then I go onto the next one.

Sometimes I get stuck in failure. I think “if only” or I think “now my life is over” or I think “why can’t it ever work” and so on. It’s easy to get stuck in the past. To get stuck in the twists and turns of what could’ve should’ve might’ve happened that would’ve changed this or that so somehow life would be better. But all of that is just in your head right now. It’s not actually what happened.

Just like we can never see really see the moon. The moon is just the light reflected off the sun. So is failure. Failure only reflects the light of our memory. It no longer exists. It’s only an imprint on our current present. With that present you stil could, you still should, you still will. This is who you are.

Did I fail? Am I a failure? I certainly failed at publishing a novel in my 20s. I failed at graduate school. I failed at many jobs. I certainly failed at many startups. At many relationships. When I look back I see a wasteland of failure. It smells, it’s rotten, and it’s piled up high. All it is is failure.

Thank God.