Understanding failure

I failed at the first two jobs I held.

It’s something that’s bugged me for a long time. I don’t think a year goes by that I don’t reflect on that. I’ve had other failures since then — and many more successes — but there was something fundamental and epic about these first two failures, and it’s only with distance and time that I’ve fully understood them.

My first job out of college was as an assistant at Viking-Penguin Books. I was shared by two departments, subsidiary rights and special sales. Essentially, I was a secretary. I did not understand that when I accepted the job.

That was the first problem.

I had graduated from a top liberal arts college with a degree in English and a passion for creative writing and editing. I had been selected as writing tutor to the freshman class, by my own professors — a paid position — and was editor of my college newspaper. I was into it, and I was serious.

That was the second problem.

People who are serious about writing and editing should not go into the book publishing industry. It’s like serious painters going to work for art dealers (which was exactly my roommate’s situation), or serious chefs going to work for sausage factories.

The third problem was, I had no idea what it cost to live in New York, and assumed a top publisher would pay me a living wage. Admittedly, this was something I should have been able to divine on my own, but I’ll give 22 year old me a break.

The only thing I walked away from a basic budgeting class with was that I was supposed to spend 25% of my net income on rent. In the fall of 1988, as an employee of Viking-Penguin, that was $250. So, naturally, I was paying double that to split a one bedroom with two other guys. Fortunately one of them was never there, so it was just me and one other guy in a 350 square foot space. I got the couch. It was what I would politely call a hovel on the Upper West Side, by far the worst living conditions I’d ever experienced, growing up in Texas and the Midwest in apartments, rental houses, and nice houses we owned or built ourselves. Even my lowest living conditions — a 30 year old rental house in East Texas — were far superior to this apartment in New York. I felt sick every day I came “home,” so I started going out and drinking what little money I had left.

I spent most of my work day filing, typing, sending teletypes — really, those five foot tall typewriting robots with paper tape spool feeders that go WHACK WHACK WHACK when breaking news comes in, though in our case they were used to communicate with someone in France — and looking for more interesting things to do.

Sometimes I read the slush pile — what was then still called “over the transom” manuscripts — fancy talk for stuff we didn’t ask for and were never, ever going to publish. Some of the submissions were from the mentally ill, people with complex, paranoid fantasies involving Jews and the Illuminati. At first it was interesting, but soon it disturbed me. The people who wrote these missives were probably on the same subway trains I rode.

We regularly got bomb threats, because Viking had published THE SATANIC VERSES by Salman Rushdie the month before I came aboard, and the Ayatollah Khomeini had put a fatwa (death sentence) on the author and publishers [NYTimes/books]. We’d clear the building, and the FBI would send dogs to our cubicles to sniff for bomb chemicals. At first it was terrifying — I imagined the bricks smashing through my body as I jostled down the fire escape stairwell — but eventually it just became an excuse to go to D’Agostinos or a bookstore and head home early, which I immediately left to go drinking.

The truth is, I was not a good employee. I was sad, disinterested, and angry. However, looking back with a little kindness on 22 year old me, I can see why.

First, it was not a good job for someone with a creative mind, because there was nothing creative to do. This was my fault. I should have known myself better.

Second, it was the worst job possible for someone who cared about books. Don’t go into the industry of something you love. This is no one’s fault. It’s natural to be attracted, and it’s not an industry’s job to amuse artists. Their job is to make profitable products.

Third, it didn’t pay a living wage. There was a reason Jackie O was an editor at Random House: She didn’t need the money. (The other reasons were: she was connected and she didn’t need to be an assistant first.) This was my fault for accepting the job without knowing what I would need to earn to live comfortably in that city. I simply thought that because other people did it, I could, too. This philosophy works fine for eating exotic foods in other countries, but is not a good approach for career decisions.

I was asked to leave, and I agreed. It wasn’t dramatic. I hadn’t screwed anything up, missed a deadline, or (shudder) mis-filed something. It was just that I was no longer pleasant to be around. The truth is, I needed the push. I had no idea how to get out of my death spiral. I remember feeling relieved.

I should have left New York, and publishing, right then.

What kept me there was ego. I hadn’t accomplished anything. I had been a secretary for a few months — a bad one, at that — and wanted to do something meaningful before I left. So, I followed up my first failure with another — I became an editorial assistant at Simon & Schuster.

[Part two, soon.]

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