I moved to Chicago in 1999. Twenty years later, a retrospective

In early 1999, I was dating a girl from college. She was a middle school English teacher, but back in college and in her high school years, she did a lot of acting.

In 1999, I was working at a weekly newspaper as a multi-hatted advertising sales, graphic designer, paper distributer and lackey. My ambitions were to make films and become a photographer.

In college, I ended up on stage for three different plays. I loved it. I likely sucked at it. But it was a rush. It was fun. And there was a kiss scene with the girl I liked. It was a great way for a shy kid from North Carolina to exact revenge on some of the idiosyncrasies I was bred to exhibit: things like a southern drawl, nervousness, painful paralyzation to think on my feet, etc.

In grade school, I remember teachers who — from the chalkboard — taught us to think that “when” and “win” or “then” and “than” or “ten” and “tin” are all pronounced as rhymes. It took a painful amount of coercion for me to finally understand, if I asked for a “pen” and received a “pin”, it was because of poor, lazy pronunciation.

We were both barely a year and a half out of college, when my girlfriend’s best friend visited from Cleveland, Ohio. We talked endlessly about our aspirations, and her best friend invited me to be her roommate in Chicago where she planned to move that coming summer.

“Chicago,” she said with a wag of her finger. “Chicago is a big city with lots to offer. And if LA or NY is too intimidating, it’s a great place to springboard into the two largest cities for creatives.”

What happened, though, was I dragged my feet, because the thought of telling my parents I was moving to Chicago to live with a strange girl I really didn’t know was nauseating. My background was strictly prohibitive of this kind of liberal minded ideology.

I think, because I would likely eventually move to Chicago, my then girlfriend pounced on the opportunity to move to Chicago with her best friend, pioneering a path for my eventuality to sign a lease there in the future.

As fate would have it, my good friends in North Carolina — the first lesbian couple I ever met who owned a frame store — introduced me to one Patrick O’Conner. Patrick was a stereotypical Irish ginger who grew up in Illinois, attended four years at Northwestern and whose divorced mother lived in North Carolina where he was living for a short period. We met and became friends. He aspired to journalism but loved movies, too.

By October, he visited Chicago on a mission to find an apartment. He signed a lease for a two bedroom in the swanky Lakeview neighborhood that would begin December 1, 1999. We were to be roommates.

I quit my job. Packed up a mattress and my clothes. My $5000 computer that was built for video editing, with a fresh copy of Final Cut Pro 1.0 on it and Patrick O’Conner and I caravanned to Chicago. He pulled a small UHaul. I drove my blue Honda Accord Coupe.

Twenty years later, I revel in the successes and continued failures that blotch together to make a never ending canvas painting that is my life. I’ve let my temper get the best of me. And I’ve let my personality flourish with experiences. I worked for the Kennedy family. I collaborated with comedians, many of whom you are probably familiar with today. I lived in the Philippines. I started my own company. I drank too much. Didn’t drink at all. I finished walking away from the faith that I was brought up in.

Twenty years later, I look back at a landscape of mountainous failures, piled high. Corpse mountains of all the dead bodies of whim, caprice and absent mindedness. Steam rises from them baking in the hot sun. Intermixed, there are hills of success. Perhaps not nearly as impressive, but somehow the failures push them up to appear stronger.

Twenty years later, I’m married to my best friend of almost 20 years. We share our time between Chicago and North Carolina. We are so fortunate to do what we do with each other. I’ve been able to surround myself with creative, intelligent friends who care deeply about us both.

Twenty years later, we are the owners of our company. We strive to excellence. We don’t settle. I refuse to compromise for anything less than superlative work.

Twenty years later, we have two darling dogs. We fought for fertility. Babies refused every opportunity. Not a day passes that we both don’t wonder what we would have been like as parents. But then again, it has afforded us a selfishly grand life of two residences, International travel, and a freedom-filled luxury of a relatively worry-free passage through time.

This life is so good, I often have to pinch myself. Nope, I’m not living in a dream.

But — in a way — I am. And it’s lovely.

With all things life living, we dream and we have nightmares. Sometimes we don’t dream at all. Ennui is par for the course. And when I muffle the noise of a hyperbolic news cycle packed to the gills with dystopian apocalypse, the singsong of songbirds tinkles in my ears.

This life is the cutest little puppy you can ever imagine. You see them and melt. And then they shit all over the floor and worms wriggle out. You take them to be professionally cured. One second they induce an eruption of body-shaking laughter. The next, you want to grab them by the nape and throw them in the trash for shitting for the third time in the foyer and also eating half of it. If life didn’t have that doe-eyed luster and the reminder of how soothing it is to listen to their breathing, while they sleep soundly and you worry you’ll roll over and crush them in the darkness of night, we wouldn’t want a puppy inflicting a fecal filled piles on our finely finished flooring.

It’s the good, the bad, the ugly and the forgiveness of self, of others, and of the mysterious ways that build up the mountains in the landscape of your hindsight that are compiled and form your present. My present anyway. And I love it.

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