How to leave.
A story about dreams.
To my fellow outlaws, outcast and misfits,
I have been getting a lot of message about “how I made it.” There are a few stories in the archive that are my early days in Los Angeles, but I have never written something on the sole idea of having a dream.
So without further ado, away we go!
I have found in my fifty-second year to heaven that to achieve something, to become something, to hold a dream in your hands, you must leave. You must leave your home, your family, your friends, and sometimes yourself. And when you come back to any of those, they will have changed, just like you, all new and old on your temporary return to what used to be.
But it is hard to leave. So hard, most folks never do it, even though they know to stay is to surrender the dream. Surrender to what? Comfort? Familiarity? The devil you know?
“I’m moving to Los Angeles to pursue a career in the entertainment industry,” I told my father-in-law.
“You know anybody out there?” he asked, the former Chicago detective scanning my face for any sign of weakness.
A year earlier I got discovered by an LA agent at the Chicago Comedy Festival. He kept asking me to move to Los Angeles, but I wanted to stay in Chicago. I had great access to all the shows in my hometown, where I could perform every night. I was also a Teamster during the day, driving trucks for the city of Chicago, with health care and a pension. Why would I want to move?
“If you want to play for the Pittsburgh Pirates, you gotta move to Pittsburgh,” the LA agent explained. “And the game is played out here.”
I had to leave everything I knew, everything I thought I was, to become somebody new, to become somebody I never met yet, to become something I did not know or fully understand.
I had to leave.
When I told people I was leaving Chicago for LA to work in entertainment, the room went quiet in a particular way. A few said it to my face. Most waited until I walked out. The question was always some version of the same thing: how do you leave a city job for something like that?
The honest answer was that it felt like I’d die if I didn’t go. Not dramatically. Quietly. The part of you that still believes in something, going dark. For good. I wasn’t being theatrical about it. It felt true in the way that things feel true when you’re standing inside them, when you know that staying means surrendering to fear and calling it practicality. I didn’t want to spend the rest of my life in a building I walked into because I was afraid, looking out a window at a city that used to feel like possibility.
I wanted to feel alive. I was willing to bet everything I had that there was still a version of me that could.
On my last day with the city, I said good-bye to my fellow Teamsters, who I love to this day. Everybody wished me well and just as I was about to leave, Hockey Joe, who up to the week prior had been all smiles, barged into the foreman’s office and started screaming, “You’re such a big shot, huh? You think you’re gonna go out to LA and do what? Be some kind of star? You’re gonna go out there and get your dick in and then what? You’re gonna come crawling back here with your tail between your legs like a fucking failure, then let’s see who’s got your back.”
Then he stormed out.
We had a going away party with my family. They smiled and wished me well. All while looking at me like I was insane, like I was marching out to the end of my life, to an irreversible fate of failure and destruction.
They were partially right. I was marching out to the end of one life and the beginning of a new one.
My first month in LA, I slept on my childhood best friend’s floor during the week and in my rental car on the weekends until I found a one bedroom in the valley. Then my wife moved out. She cried for two weeks straight. She missed Chicago and she missed her family.
“I hate this place,” she said.
At the end of the first two weeks, the agent who told me to move out quit the business and nobody at the agency would take my calls. That same day I got the letter to start the fire academy back in Chicago. All I had to do was fly back home and I could be a fireman. My mind raced, luring me back to safety.
“Fuck this city. Move back home. Get on the fire department. You’ll work 88 days out of the year, pull down a 100K, have health insurance, and you can write and perform whenever you’re not working.”
But there was more than fear taunting me. I was also an alcoholic, disappearing for days, often coming to in alleys and dumpsters.
So to live, to breathe, to survive, I had to add a new dream to the list, a dream that would have to be the center of all the other dreams: sobriety. I thought giving up the drink would be impossible, just like my other dreams, but it turns out it only felt impossible. I got sober and six weeks later my wife got pregnant. My wife was a reluctant passenger in the pursuit of my dream and now there was a child.
I ruined everything. I ruined her life and I was about to ruin the life of this little child. For what? A dream? Why did I ever have the audacity to dream? How could I ever think or believe I could afford to dream?



