How To Survive Failure

This newsletter is my process of writing a self-help book, tentatively titled How To Make Money: Financial Advice For Poets.

Obviously, none of this should be taken too seriously.

When I was 13 (almost 14), a couple of weeks after my mother died, I ran away from home and I never went back. The story of that year, my eighth grade, is complicated and I wrote about it here. But the summary is that I mostly slept outside, and I learned a terrible lesson: That I could survive.

When you walk away and it works out, sometimes you get in the habit of walking away too soon. If you think you don’t need people you might not value relationships as much as you should and you might not develop the skills to succeed in a group environment.

Life is a group environment.

Someone once told me, or I made it up, that every story is a love story or a story about loneliness. It takes a long time to realize that there are no good stories about loneliness (except maybe Taxi Driver).

We don’t think enough about the problems with the lessons we learn. Or that a lesson can be useful for a time but eventually you have to learn new lessons. The new lessons might contradict the old lessons. That’s just how it is.

This is the difference between growing and getting stuck. As I get older (I’m almost 50!) I’m amazed by this; I’m struck by the fact that I’ve written 8 books, all of them very autobiographical, and yet I realize new things about myself all the time. I literally don’t know myself at all. I think most people have this experience, finding out that they were wrong about things when they were younger. The difference, when you’re a writer, or if you write the way I do, is that I’ve written my mistakes down. I’ve been wrong over and over, and it’s very well documented.

I want to give some examples of this, of why it’s important to be wrong and why it’s important to believe in things deeply and why it’s important to change your mind and change it back again.

I’ve never been good at learning, but I’ve had strange bursts of confidence that enabled me to get things done between crippling bouts of depression. Which is how I wrote my first 3 books. The problem is that they weren’t very good. They were good enough for someone to publish but not by much. Then, at the same time I sold my books, I was awarded a Stegner Fellowship to Stanford where I came in contact with other writers and I learned to appreciate the books they read. I was the only writer that hadn’t studied writing before so I was hoovering everything this incredibly talented group had picked up from the best creative writing programs in the country. In particular I fell in love with Raymond Carver and Mary Gaitskill and then Jesus Son by Denis Johnson, which I kept on my desk for 2 years. And I came to hold a set of beliefs of what good writing was, and wasn’t.

I believed in minimalism. I was against adverbs, adjectives, and backstory. I was against explaining and narration. I was never going to tell you why a character did something, all that mattered was that it was possible. I hope you can see where this is going. Leaning into this sort of literary fundamentalism I wrote my first good novel, Happy Baby. The lesson, in retrospect, is that to write a good novel you have to have strong beliefs. But also, any strong beliefs about art are inherently wrong.

That’s the dilemma. You have to believe in something, but truth is ephemeral.

I wrote a book which I still think might be my best, but then I couldn’t write anything, for years. There was nowhere for me to go, I’d written myself into a creative dead end. Years later I finally got out of it by taking up non-fiction and writing The Adderall Diaries, a book that is full of tangents and non-conclusions. A year after writing The Adderall Diaries I started a popular web magazine, which, similar to my writing trajectory, was good until it wasn’t. And a year or two after that I discovered the writer Roberto Bolano.

Now I just read Bolano novels and stories over and over again (it helps to have a terrible memory). And occasionally non-fiction if I want to learn about something new. Bolano will destroy any notions you might have formed about what constitutes good literature.

So back to the original example. When you’re 14 you can survive on your own. You can sleep on the streets in a Chicago winter. But I wouldn’t be able to do that now. Not even in Southern Florida. Running away was a good decision but learning that I didn’t need people was the wrong lesson. If you think you know things that other people don’t know it can be hard to learn from other people’s experience. Which means you’re going to have to make all the mistakes yourself.

That’s what I did. The result was that most of my books were published without an agent on small presses. I signed bad contracts. I directed a successful feature film with a bunch of famous people but couldn’t turn it into a career because I was too busy fighting with agents and producers and not trusting people. I had advantages obviously: white, male, confident in spite of myself. But I never learned how to be an insider, which is where the real money is.

And the benefit of all that is I got a lot done I would never have gotten done if I had waited. Those lessons enabled me write books and make movies and create political organizations. I stopped American Apparel from opening in the Mission District in San Francisco. Rush Limbaugh did a whole segment about me. But if you’re in the Mission now you can see an American Apparel would fit right in. It might even be an improvement.

I’m going too long again, and not getting to the point I wanted to make. Here are two important lessons I learned from my four years in various Chicago group homes as a ward of the state that are still objectively true 35 years later.

When I first entered the system I was locked in a public mental hospital for 3 months. This was not a good place and you would only end up there if you were a ward of the state which meant, by definition, you didn’t have any advocates. But I went to synagogue while I was in the mental hospital. I was the only Jewish kid in synagogue (ok, 1/2 Jewish). Most of the other kids were black and we were all there for the same reason: it was on the adult ward so we could smoke and also the Rabbi brought cake.

A year later, when I was kicked out of a very rough group home on Chicago’s South Side I got picked up for a home with the Jewish Children’s Bureau. Because of that Rabbi. This is the equivalent of failing out of Junior College and being offered a full scholarship to Harvard. It’s not a thing that ever happens. And it no doubt saved my life.

Did I ever thank the Rabbi? I did not.

The lesson there is not everything is in your control, but go to Synagogue. They say there are no atheists in foxholes; there are also no atheists in Alcoholics Anonymous.

While in the JCB, after failing two years of high school, I decided to quit drugs and make an effort to graduate on time. It’s not hard to get good grades in a group home school. What was miraculous was the attention (from adults!) and resources I received when I started to do well. There are tons of resources for kids who are wards of the state when they do well. I didn’t have to pay for college, someone helped me get an after school job, the group home lifted my curfew. When I speak at juvenile detention centers, something I don’t do anymore, but did, for a while, I would always point this out. Everybody wants to be on a winning team. Start helping yourself and you’ll be amazed what others will do for you. It’s absolutely the best lesson a kid can learn. I tell the kids that the end result of all this was to meet Michael Jordan and get to fill up a free shopping cart (actually several) at the Nike Employee store. There’s no better way to inspire wayward children than free Nikes.

Of course, when I spoke with adult volunteers I would say that kids needs consistency, and second, and third, and fourth chances. You tailor the message.

And that’s how you survive. Except it’s complicated. None of that stopped me from overdosing on heroin when I was 24 and making any number of mistakes along the way. But the lessons remain the same. Just don’t learn them too well. And change your mind often.


p.s. My next letter is going to be much less self-centered. I have interviews set-up with a real estate wholesaler and an options trader, so hopefully I’ll be bringing some practical insights in the near future. I’m going to write at least 2 more letter before delving much into my personal story again. For balance.

p.s 2 There are so many new subscribers after my last letter. I thought, I’ll never be able to write another letter. What’s interesting is the new subscribers (and you are the majority) are actually interested in Self Help topics, which is what I am most interested in writing about. People who are interested in self-improvement are nicer than people who are interested in politics. So thank you for being here. You’re nice!

If you’d like to catch up on previous topics, depending on your personal interest, this is how the previous issues break down.

Fixing Stuff:

8: How To Fix A Sink 13: How To Fix A Shower And A Bed


12: How To Get Paid For Your Art (this one is pretty obvious) 7: How To Publish A Book 6. How To Make A Movie (this one is very practical, actually)

Real Estate:

14: The BRRRR Method 11: Appreciation 10: Cash Flow 9: How To Buy A House

And then the earlier ones which are mostly basic financial stuff for poets, things like micro-marketing, collaboration, and if you go back to the first issue I lay out how to make $10,000 a month in passive income.

p.s. 3

I’m going to come up with more benefits for paid subscribers. Maybe full interviews I do with the subjects of some of these letters. But currently paid subscribers are allowed free consulting on any of the topics covered in these newsletters.

Thank you for being here. Please share this newsletter on social media. Likes and comments are very much appreciated, it’s what keeps me going.