How To Handle Failure

Earlier, I wrote an essay about how to handle success, which is vastly more interesting. But writing about failure is easy, because it comes naturally to me.

I have failed at nearly every single thing that I have done.

·      First of all, I was physically abused as a child.

·      I was raised by a single mother in not-quite poverty.

·      I was bullied occasionally.

·      I was held back a year in Little League.

·      I got poor grades in middle school.

·      I got poor grades in high school.

·      I didn’t make the varsity baseball team.

·      I got spit out the bottom of the tennis team.

·      I almost got in serious trouble one time.

·      I got poor grades in college in spite of having the 3rd-highest SAT scores in my class.

·      I almost got kicked out of college, which effectively ended my career in the Coast Guard.

·      An injury ended my wrestling career.

·      I was denied a command endorsement.

·      I never made Senior Vice President at Lehman Brothers.

·      I was paid half as much as my peers.

·      Ultimately, I failed at Wall Street.

·      I spent three weeks in a psychiatric ward.

·      I have battled a variety of addictions.

·      I have the slowest-growing newsletter in the history of newsletters.

·      My first book was a failure.

·      My second book was a failure.

·      My radio show was an expensive failure.

·      These essays are a failure.

·      None of the mountains of content I have created over the years has ever gone viral.

·      My music career is a struggle, to say the least.

There have been some successes along the way. But I have failed far more than I have succeeded.

I have about 1000 words to go. Now, I could write something treacly and embarrassing about grit and resilience, which is a fashionable thing to write about these days. There are millions of essays like that out there. They could be written by ChatGPT.

I want to tell you that failure is really, really hard.

One of my toughest failures was my first book, Street Freak. I had such high hopes for that book. I mean, how could a book about Lehman Brothers, released only three years after the financial crisis, on the same day that Occupy Wall Street started, underperform? I am not much for airing dirty laundry in print, but let’s just say that the book ended up with the wrong publisher and the wrong people and everything that could go wrong, went wrong. And it was heartbreaking. I was bitter about that for years. The book was remaindered, you know. I’d tell you the sales figures, but they’re pathetically low. When I tell people those sales figures privately, they’re shocked.

And the reason they’re shocked is because that book has become part of the Wall Street lexicon, held in the same regard as Liar’s Poker and the other great Wall Street memoirs. And think of it this way: there are only 500 books published by the Big 5 publishers every year, mostly by people who are already famous in one way or another, and Street Freak was one of them. And it had a huge impact on people. I’ve had so many people reach out to me to share their struggles with mental health.

So it really is a matter of framing. All the failures I listed earlier could also be viewed as successes. If I had gotten the command endorsement my first tour in the Coast Guard, I’d likely still be in the Coast Guard. Or not—if I had gone through those same mental health struggles while in the military, I would have received a lower standard of care. And I would have lost my security clearance, and bounced out of the service in ignominy. So things worked out for the best. And if I had made SVP at Lehman Brothers, I’d likely still be there, too—and fucking miserable, and a nervous wreck. So things worked out for the best.

When I reflect on my life, every hardship I’ve gone through, every failure I’ve experienced has been for a reason. It wasn’t suffering for suffering’s sake. There was something I had to learn from each of those experiences. So you fail, and you learn, and you get smarter, and you fail at different things, and you learn, and you get smarter still. But you never quit. There is a time to quit, eventually, but if you quit before it’s time to quit, it’s undignified. And if you give up, and never try anything again, you are a loser. And I don’t use that word lightly, because of the connotations.

Writing is a particular source of suffering. Sometimes when I think about my middling writing success, I think about my favorite writer of all time: Barry Hannah, the greatest writer who ever lived, who never sold more than 7,000 copies of any of his books. And yet, most of the world’s great writers consider Barry Hannah to be their favorite writer. At the time of writing, this Substack has 5,426 subscribers. It gets a huge amount of engagement—read rates in the high 60s, dozens upon dozens of likes, but it doesn’t grow. And somewhere out there, some 25-year-old nincompoop has clickbaited and growth-hacked his way to 50,000 subscribers. So I keep doing what I am doing, and plow forward with the idea that if you just keep putting in the time and writing something approximating literature, then good things will happen.

In 2016, leading up to the release date of All the Evil of This World, I got 100 galleys printed and sent them out to luminaries in print, TV, and Twitter. I might as well have been told to go fuck myself. Nobody helped. At one point, I sent a Twitter direct message to an editor at Fortune, angling for a review, but I accidentally referred to him as an editor at Forbes in the DM. He took a screenshot and tweeted it, ridiculing me. My heart was pounding. My ears were hot. This book was shaping up to be another failure, and this asshole was mocking me. I was sitting in my office, and I remember talking to myself—I never talk to myself. I said, get back on the horse, and set about sending out more cold DMs and emails. None of it hit. The book generated a huge amount of controversy, resulted in scores of negative reviews on Amazon, and never sold more than 3,000 copies.

Framing: I consider it my greatest achievement, and I’m not kidding.

Nothing I have done has ever gone hockey stick, and I have done a lot of things. I have a third book coming out, and a fourth. I have high hopes for the fourth. But who knows—maybe it will be yet another failure. People close to me know that I am always working on a bunch of projects simultaneously in the hopes that something will take off. Nothing ever does. But I keep trying. I never give up. And there has been a great deal of suffering along the way.

The corollary to all of this is that suffering is how we grow. Look at any successful person, and they have scars. There is an old saying: “After twenty years, he was an overnight success.” Whenever we see a successful person, we don’t see the years, even decades of work that goes into it. And as for as the 25-year-old nincompoops go, that success is transitory. They have never experienced love. They have never experienced pain. And the first time life throws them a curveball, they’ll shrivel up and blow away. Successful people give off the impression that life is easy. But nothing could be further from the truth. They are sitting on top of a big pile of failures.

Life hands you a bag of shit, sometimes. Bad things do happen randomly, though not very often. It’s about how you clean up the mess. For as many professional failures as I’ve had, my life has been relatively free of tragedy. No car accidents, no cancer, no unexpected deaths of family members. I’ve been lucky, and some people have real problems. It really is all about your attitude. And remember, if you’re going through hell, keep going.