Careers in the arts are tough. So much so they are actually a series of part-time freelance gigs wrapped in the word “vocation.” Ones with no employee benefits, and retirement is whatever you can save when not eating Ramen.

I’m at a weird place in my career as a writer, teacher, and historian. For four years I’ve tried to do EVERYTHING to make money and generate opportunities. It’s led to amazing stuff happening. New book series with rave reviews, with the sequel coming out in the next year. Major history project completed and debuting this summer. I also secured a contract gig teaching Creative Writing classes for Google employees! Yes, that Google.

So, how the hell did that happen?

Simple! Fear, imposter syndrome, and poverty.

Easy to replicate, no? Okay, here’s the story.

The Gutters was all about the seventeen years I spent trying different stuff, pursuing interests, and living a life of failures, stupidity, success, and achievement. But within at least one of my professions (history) there had been the allure of stability: academia. When I got my doctorate, however, the academy had changed. I won’t bore you with common knowledge, but a sustainable living with benefits as an academic in the USA is for the 1%, primarily those from the top five schools. I wanted that stability. I wanted to write big, contextually rich, detailed and depth-oriented books on esoteric topics that pushed human knowledge a smidge. I wanted to teach big and small classes and advise on grad theses. I wanted to fall asleep in faculty meetings.

That was the map my mentors had given me. And it was fifteen years dead in the water when I graduated. I got part time, no-guarantee adjunct work. But not enough to live. The old map would kill me.

I had to make my own map to survive America.

This map was part lottery, part strategy, and part saying “yes!” to everything (riffing on Chris Hardwick’s Confidence Theory). I’ve talked about all the jobs I had before my life calmed the hell down, but among the most important and the one I resisted the most was teaching writing.

See, in 2013, I considered myself a failure as a writer. No career. No book deals. Just a bunch of ebooks and short story sales. What the fuck could I teach anyone? I couldn’t even teach history! Imposter syndrome, depression, and grief stained my thinking.

But when you’re running out of canned goods to eat, you can’t be precious. You need to try. My only rule in life is if you do nothing, nothing will happen. I didn’t want to fail, but I also wanted to eat.

So an adult-learning annex gave me a shot when they didn’t have to, thanks to having history teaching experience and being vetted by a friend, Nick Mamatas, who is a far better writer than I. Lots of mistakes were made getting that class running, but I also discovered I had a knack for giving students intensive and helpful feedback on themes, symbols, and motivations in their work.

Writing from the Heart became my flagship class for four years. It helped keep me alive. I used everything I’d learned reading shitty writing books, going to Odyssey, doing improv, living my own personal experiences, and listening to the experiences of writers whom I loved and some whom I hated (a common phrase I use is “X wrote a writing book, which is shit but had this nugget of wisdom”) to make this class special and valuable. I turned it into the kind of class I would have loved if I’d just been starting out. And I give my students everything I got as a teacher. I never phone it in. I look pretty ragged when it’s done, but I want to give my students all I can!

And one day, one of my students tossed my name in the hat of his employer as someone who is a great teacher for beginners. That lead to a chance to teach at Google for their employees.

This is the gift of unintended consequences. Of making connections because you bust your ass and give folks the best of what you can offer. And done with zero expectation that it would lead to anything beyond the task at hand. And it would never have happened if I’d kept listening to that black static in my head that I wasn’t good enough to teach a class I was clearly born to teach (because I made the sumbitch).

That voice was stymied because of the harder reality of being poor in America. I had to be cool with failure. I had to be cool with shame, embarrassment, and worse. And I had to keep hustling, in case it burned out. But I couldn’t afford to not try. My ego wasn’t important. It didn’t matter an iota. I needed to eat.

Creating this class was not on the old map I’d made for myself. But when the BE-AN-ACADEMIC map turned to dust, I had to make another. My own. It doesn’t look like anyone else’s because how could it? How many left-wing military historian, creative writing, pulp novelist, improv-and-sketch comedy performers do you know?

I had to make my own because the circumstances of my life have no single model. I’ve had to follow a dozen paths to make my own. Thus, my map has shifted and changed over the years. It must change. Nothing is certain in a freelance life, and my successes have allowed me to close off some sections of the map (like teaching high school and some online learning) to make room for others.

I’m keeping this in mind because I feel the same kind of fear emerging as I try and grow another part of the map. When my life crashed, I was an unemployed historian and short story writer. Right now, I’m a published novelist and popular historian who teaches at Johns Hopkins University and Google.

Yes, that’s a brag. But unlike most who succeed, it doesn’t prove the system works. And it could vanish in a heartbeat or an earthquake. So I want to make it better before another wave of uncertainty crashes. And my old tools and strategies might be getting in the way. When you’ve got nothing to lose, you have no choice but to try everything. But when things find purchase, how do you keep good stuff happening?

How do you grow when all your guts and instincts are still in survival mode, demanding you work until you pass out? How do you pick your battles, rather than fight a nine-front war of five jobs? How do you review the data of four years of successes and holy-crap-failures to make things better?

You make a new map.

And that scares the shit out of me.


Help Jay sleep at night by buying HEX-RATED, the debut novel in his new series THE BRIMSTONE FILES, or FXXK WRITING: A GUIDE FOR FRUSTRATED ARTISTS