A Decade in Chicago, Ten Years of Mastering Disappointment
“Trouble creates a capacity to handle it.”
—Oliver Wendell Holmes
I pulled up to my girlfriend’s apartment in the mid-afternoon. My left arm was exceptionally darker than my right from hanging it out of the car window during my week-and-a-half drive from Las Vegas to Chicago. I reeked of road dirt, midwest wind, beef jerky and Red Bull. I hadn’t shaved or showered in six days and I needed to take a crap desperately.
Finally, after a decade of imagining it, I had arrived in Chicago. The Big City. Home. Although I didn’t look the part, I was ready to take the place by storm. Within three months, it was clear that instead, Chicago was going to bend me over its knee and spank my ass red with the rotten corpse femur of Daddy Daley while I helplessly, and more and more self-destructively, took the beating like a frightened little bitch.
It’s not quite fair that I called Chicago home upon my arrival. I’d never lived in Chicago proper. I grew up in Flossmoor and my only real experiences in Chicago involved punk shows at the Fireside Bowl, trips to the museums and Loop theatre productions, a few fancy dinners downtown, the Christmas windows and elves at Marshall Field’s, Passover in the ballroom at the Carlyle and White Sox baseball games. I visited Chicago a lot. And I never longed to live there. The thought never crossed my mind.
But when I moved to Las Vegas to attend college, Chicago instantly became a destination for me—my home for which I pined. Throughout all the emo-fueled heartbreak I experienced in my late teens through my late twenties, the longing for Chicago was always present among them. Why? Because Las Vegas wasn’t a real city. Because Chicago had a useful public transportation system (which I’d never used while growing up in the south suburbs). Because Chicago had Mike Royko (even though he was quite dead before I moved to Vegas). Basically, it was because I was a young blowhard who refused to be content with his station in life and took some strange joy in chest pounding around Las Vegas because I was from the third largest city in the Union and we had two major league baseball teams. How many did Las Vegas have? None. So there.
Yeah, I was an asshole. More importantly, I was wrong.
There was nothing so terrible with Las Vegas. I just needed to get used to it, find my place, make my home. And I did. The decade there was, unsurprisingly, a fantastic decade. I was in my most formative years, 18–28. I made some of my best friends. I had some of the strangest, wildest and funniest experiences that, when I think back on them, are almost hard to believe. Hell, it’s why I think the Hangover movies are so stupid. I lived a version of all three and my version was weirder, had more celebrity encounters and people actually died. Eat shit Hollywood. I digress… I worked a lot of different jobs. I became a writer and a radio deejay. I built a radio station at UNLV, I did a lot of standup comedy and hosted my own room. I had a lot of sex. I witnessed that frontier town grow at an insanely fast pace around me. I bought a home with a pool in the backyard. I swam naked in that pool and became a responsible homeowner. A lot happened while I lived in Las Vegas and I ended up having a great time essentially achieving manhood—adulthood—there.
But Chicago was always in my sights. Once I got past my angsty bullshit, Chicago became a destination because it was, actually, a bigger city. There were larger institutions I wanted to get my radio and writing and comedic skills in front of. And yeah, the majority of my family was in Chicago. The goal became reasonable and truly righteous.
So as the decade in Las Vegas neared, I took inventory of my life. I was making decent money. I was working a lot, writing for a lot of different publications. My standup was going well. I was as confident as I’d probably ever been. I concluded that this was the time to make my move. It had been 10 years. I had momentum. Now was when I had to propel myself to the next stage, which was Chicago.
It’s important to note here that the final catalyst to the move came in the form of a woman. And don’t they always? A few months before the move, I started a long-distance relationship with an old college friend of mine who still had family in Vegas but currently lived in Chicago as an aggrandized corporate drone at one of those big aggrandized companies downtown. We were both excited at the prospect of what the relationship could be, so with my confidence in full swing and a girl waiting for me at the other end, I gave my day gig two-weeks’ notice, broke the news to my friends, arranged for my best friend to live in my house until I could sell it, stuffed my VW Golf with as much as I could and headed out.
The one thing I didn’t to do was line up work for when I arrived in Chicago. But I wasn’t worried about that. I'd get something. How could I not? Who wouldn't want me? I was talented and a successes. Instead of rushing there or being professionally and financially prepared, I’d take a lengthy road trip by myself stopping along the way to visit a few friends in California, scoot up into the Pacific Northwest, maybe peek into Canada, scoot through the northern states and come on down via Wisconsin. I would see some things, meet some people. Bask in America. It would be my last youthful hurrah before finding a job and becoming Chicago’s greatest import since Al Capone.
What I didn’t know and couldn’t have planned for was that the economy and the tarot cards of my life were about to take a total shit right on my face.
Everything is terrible
I pulled up to that girlfriend’s high rise apartment on Lake Shore Drive on June 8, 2007. The market for creatives, such as myself, was starting to seize. Shortly thereafter, the housing market stalled on its ascent and then plummeted. I struggled to find a job and opted to take my house in Vegas off the market. I humped real hard for freelance work but the pay was horrendous. I did a bundle of stories for RedEye and Metromix, mostly covering bars and restaurants. I actually lost money on these stories. They didn’t reimburse for the meals so between that and the parking, and the bus and train rides, and the requests to re-write and re-re-write so that the story was void of all writer influence, it just wasn’t worth it. On top of that, RedEye rejected several of my pitches only to hand them over to their staff writers. I’m not alone in this experience. Fuck the RedEye. It is all that is wrong with journalism.
I struggled to get my byline anywhere else. The other publications in town either weren’t accepting freelancers or weren’t paying freelancers. Marketing and advertising positions weren’t available. I signed up with a few of those talent placement companies that brokers freelancers out to companies, and in my interview with one agent, I was told, “There just aren’t any jobs right now.” I didn’t have the kind of connections and clout I had in Las Vegas. This was hard work, which I didn’t mind, but I felt more and more that I didn’t know how to hustle because I was getting nowhere.
I was forced to take an inside sales job at CareerBuilder, which is the height of irony, because CareerBuilder for me was career purgatory. And when the financial market collapsed in 2008, kicking off the Great Recession, CareerBuilder laid me off. As the suit from the corporate office broke the news to us that Friday afternoon, he encouraged us to use the CareerBuilder services in our searches for new jobs. I laughed and told him that I already had my resume on Monster.com.
On top of all that, the relationship with the live-in girlfriend was rotten and emotionally abusive. She was awful to me and I was awful to be around. Shortly before I arrived in June, my parents finalized their divorce. Navigating those strange and choppy waters was hard on my sensitive little heart. I was unemployed. I had no money and no prospects. There were times when she was understanding but mostly she would berate me for not earning enough or being able to get steady work. She once attempted to prove to me just how much of a failure I was by saying, “You’ve been fired from every freelance job you’ve had.” I explained to her that there’s a difference between being fired from, and completing a freelance job. The two are mutually exclusive. But what did she know? This was a girl who was making $175,000 at age 28. Her understanding of the struggles of a new writer living in Chicago while the economy was crumbling all around was non existent. But like I said, I was awful to be around because I was miserable at every turn. And she did little to help. Unless you consider helping accusing me of abandoning her and possibly cheating when I would be out late performing standup at open mics in quiet bars occupied by seven other male comics.
Keep your chin up and your head down, I like to say. It’s good advice. It’s not something you’d find on a faux distressed wood sign for sale at Target, but it’s rational advice. Heh, perhaps you won’t find it on one of those stupid signs because it’s rational advice.
So why didn’t I leave her? Looking back on it with several years of hindsight that arrived almost the moment we finally broke up, I can tell you that it was because I needed a place to live. She covered my share of the rent—and gave me shit about it—when I couldn’t afford it. If we broke up, I’d have to live with my dad in Flossmoor. And that wasn’t an option. It had become a broken home and my nerves were no longer steeled. I was fragile. The thought of it depressed me even more. Moving in with my dad in the house where I grew up would be undeniable proof that I had failed. Lying to myself about the condition of this relationship with that girl was the morphine that staved off just enough pain to keep me living.
Those first three years in Chicago were hard. I spent a lot of time in a hard state of loneliness. Never alone, but lonely. Depressed, hopeless, aimless and rudderless. Unemployed, convincing myself I should continue to love a girl because I needed a place to live in the city, void of all confidence, I realized that I had made a huge mistake in coming here. And then things got worse.
My dog died. My grandfather died. And then my best friend died. Yeah, the one living in my house. It was a drunken screw up on his part but one that shattered me. That was the final chink in my tinfoil armor.
There was not enough booze in all of Cook County to calm my sadness, anger and fear. Finally walking out on the girlfriend was the turning point. Yes, there were little wins along the way. I hooked up with The Second City as I’d done in Las Vegas. I made some friends beyond the too rich, too soon bummers that were the friends of that girlfriend. I wrote some shows. But with the girlfriend out of the way, I was free to struggle without reservation or accountability. And that made all the difference.
A few months later, that stupid resume on Monster actually landed me a decent-paying gig. It was full-time and in Aurora, but it was money. It forced me to quit the drinking habit. It gave me a bit of confidence.
New freelance opportunities were being discovered. A magazine publisher asked me to be the founding editor of Chicago Health magazine. There were more Second City shows and others beyond that. I got a small book deal. And when that Aurora job laid me off, I had enough freelance work to keep going without it. Plus, I had been through the shit. It was hardly a set back. I made more friends—artists and writers and photographers, musicians and actors—interesting people with interesting desires and stories. I hooked up with creative agencies. I found selfless purpose in helping others through Gilda’s Club Chicago, which admitting to like that makes it not so selfless, but you get my point. Slowly, the reason I had come to Chicago was revealing itself as happening.
Becoming the Master
I am, of course, condensing the story of my last (first?) decade in Chicago. The point that I’m trying to make is that when I arrived here 10 years ago, I gauged the time in weeks, then months and then years. It’s still difficult for me to say that I moved here 10 years ago because it doesn’t feel like it’s been that long. At times it feels like it’s been longer. But then, other times it feels much shorter. And in a way, I’m right on both accounts. Longer because of how slowly those first three years dragged on. How nearly every day was a trudge through waist-high drying concrete mixed with clay, mud and human shit. And then shorter because those first three years are easy to separate from the latter seven. Because I didn’t really arrive in Chicago until 2010. Not the me that I’m proud of or enjoy. Mostly, anyway.
It’s hard to look back on the 2007–2009 years of my life. When I do, I’m still shaken. There’s a kind of PTSD that I carry with me, and sometimes I catch a glimpse of the parts of me that those years beat down and distorted. The good parts of me. I tend to be a little gun shy when it comes to certain things now. Like getting married. My poor, long-suffering Katie. She was the victim in a war that began and ended before her time. I recognize the failure that leading with emotions brings to most situations. This has caused me to be less apt to recognize and, at times, respect emotions at all. Those years made me a touch sociopathic, maybe. I don’t know. Perhaps it’s just scar tissue. Yeah, that’s it.
But it also made me certain of one thing, and that's that everyone is living with deep, thick scar tissue. There are things that occurred years ago, decades ago that we are still processing, still reeling from, still trying to make our way back to the light after having been sucked down into the darkest dark. We get rattled. Those first three years shook me like a San Francisco earthquake.
But things are OK. For now. I know that terror lurks around every corner. At any moment, we can lose things important to us like our friends, our pets, our family, our jobs, ourselves. But if we are prepared for the horrible, we can seek out the fantastic. It’s hard to not get weighed down by the muck and to keep your head above the shit line. Keep your chin up and your head down, I like to say. It’s good advice. It’s not something you’d find on a faux distressed wood sign for sale at Target, but it’s rational advice. Heh, perhaps you won’t find it on one of those stupid signs because it’s rational advice.
I have to remind myself of this because sometimes I get worried that successful moments, joyful moments, long-term exciting contentment will evade me eternally. It can make it difficult for me to be around. (My poor, long-suffering Katie.) It can make it even more difficult to be me because that kind of fear, being afraid like that, is me at my worst. Fear in any form quickly leads us to our worst.
I have to keep my chin up and my head down. Think things through but never settle, and avoid complacency. Things can always be worse but they can always be better, too. Riding that fine line to the end without coming off the rails and crashing down on either side is the only way you’ll ever master disappointment. It's not always easy, but not always easy after long enough becomes a lot less hard.