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Greg Baugues

lives in New York and serves on the developer evangelism team at Twilio.

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Today is my eleventh Chicago birthday.

I moved to Chicago on March 22nd, 2005. But that’s not the day I celebrate. I celebrate March 23rd: the first day I woke up on a used futon mattress on the floor of a shitty apartment in a great city with a chance to start over.

I failed out of college two years earlier. I didn’t know it at the time, but I was suffering from bipolar disorder. I moved back in with my parents in Indianapolis and started doing freelance web development. I thought that maybe if I spent my days doing something I enjoyed instead of school that life would get better. It didn’t.

I only had one real client: a guy named Andrew out of New Jersey who needed a lead management system for his roll-off containers business (“street dumpsters” to the lay person). I’d find out a few years later that there were (unsurprisingly?) some mob connections.

My M.O. was to agree to a deadline, try in vain to start working on his project all week – staying up until 6am saying, “I’ll start in 15 minutes” or “Just one more episode of the West Wing.” At best I’d start at 2am the night before it was due. Typically I’d just sail past the deadline, then start dodging Andrew’s calls and emails, being too ashamed to admit that I had nothing to show for a week’s “work.” After a few days he’d start calling the house phone, which my dad would answer, so I’d have to leave the house in the morning and spend all day at Panera and Barnes & Noble, trying to stay out until after my dad went to bed so that I could avoid answering questions about Andrew and the $400 car payment that I owed my parents but hadn’t made in months.

Eventually, I’d get the work done. Guilt would push me to agree to do more for no more pay. This was before I knew the words “scope creep.” The project lasted over a year and I made less than $4000.

In January, my best-friend at the time, Jie, convinced me to make the three-hour drive to Chicago to hang out with a friend who was in his second year of law school at the University of Chicago. After fighting through the Friday traffic – traffic that had previously convinced me I wanted nothing with living in the Big City – we met Gao in Hyde Park on the second floor cafe of a Borders, back when that was a thing.

Gao was sitting at one of the five chess boards set up on the long wooden. Aside from Gao, Jie, and myself, the only person at the boards who wasn’t a middle aged black man was a white guy, about my age, with dreads down to the middle of his back. He wore baggy track pants and a noticeably torn and hoodie. His lisp made it obvious that he had grown up in a part of town very different than my white middle-class neighborhood in Indianapolis.

His name was Jason, and he was not only winning his games, but dominating them. Turns out he and Gao knew each other well. After Borders, Jason hopped in the car and played tour guide for the rest of the night, taking us to a hip-hop club called Subterranean in the not-yet-fully-gentrified neighborhood of Wicker Park.

For the rest of the night, Jason and I sat shoulder to shoulder, chain smoking and having one of the most intelligent, thoughtful and philosophical conversations I’d had in years, despite the fact that he ended nearly every sentence with, “knaw wha’ I mean?”

When the club closed at 1am, we drove to Greek Town, just across the expressway from the skyscrapers of the Loop. It was an authentic Gyro place. I ordered a hamburger and fries. It’d be a couple years before I was comfortable trying any kind of ethnic food.

We didn’t get back to Hyde Park until 4am. Jie and I slept on the floor of Gao’s 200 sqft. studio apartment. On our drive home, I kept thinking, “I would never meet anyone like Jason in Indianapolis.”

A few weeks later, I got into a car accident. Still clinging to the obligation of completing college before starting my “real life”, I set out to drive two hours to the University of Illinois to retrieve my transcript in an attempt to transfer credits to Indiana University’s Indy campus. I didn’t tell my parents that I was making the trip. I hadn’t been totally transparent about how I really didn’t have a plan for completing school. I’d eventually lie to them and tell them that I graduated from IU despite having attended only half-a-dozen classes there.

Before my trip even started, I hit a patch of black-ice while merging into traffic from the on-ramp of the expressway. My car did a 360 across both lanes, somehow missed all the other cars and collided with the dividing wall, fortunately at low-enough speed that my airbags didn’t deploy (or perhaps they simply malfunctioned). I was facing the wrong direction, but my car was drivable. I drove back the wrong way down the on-ramp, pulled over at the nearest gas station and called my parents.

That crash was a catalyst. Something about being stopped cold in an attempt to revisit the place that represented my greatest failure while on a desperate errand to continue the path that I was “supposed” to be on.

I needed a clean slate. I didn’t know what I wanted to do with my life, but I knew that there would be more opportunity to figure that out in Chicago – and once I figured it out, more opportunity to do it. I figured the worse case scenario was that I’d run out of money and move back home with my parents, which meant that I was currently living in the worst case scenario.

I had nothing to lose.

I started looking at apartments on Craigslist and left a few voicemails. A few weeks later I took a Greyhound up to the city for a scouting trip. Minutes before pulling into Union Station a landlord named William Restrepo called me. In a thick Colombian accent, he asked if I was still looking for a place. I told him I was. He told me to take the Blue Line to the Damen stop, just around the corner from Subterranean. He told me he’d pick me up there and show me a couple of his places.

When I got off the train, William was waiting in his F-350, the most impractical vehicle I’ve ever seen anyone drive in this city. I climbed into this stranger’s truck and we drove half-a-mile down the street to 2321 W North Avenue – one block east of Western Ave, commonly considered to be the dividing line between the “good” and “bad” parts of town.

As soon as I walked into the place, I knew it was my future home. It was a four bedroom apartment on the top floor of a three-flat. William rented out each bedroom individually. The stairway opened up directly into the living room. It had so much character: hardwood floors, an ugly orange paint job, original woodwork, and bay windows that overlooked the busy North avenue where we’d spend many nights watching Johns get busted for solicitation. The furniture was tattered. The shower was a trickle. The kitchen was ugly green tile. No dishwasher. No laundry. No A/C. It reeked of smoke, which was fine, because I smoked and smoking in the comfort of my own home seemed a bit of a novelty.

For $400 per month, I got the largest bedroom of the four. William had kicked out its previous occupant when he caught the kid selling coke. William also flushed the kid’s stash down the toilet, which struck my roommates as a bit… dangerous. But these things didn’t concern William as much as they did us gringos. The room had been vacant ever since. The window pane had a hole the size of a fist. William offered to cover it with plastic.

A few weeks later I packed my car as full as I could get it, still imbued with the suburban mentality that more is better. I had $1,200 from my last check from Andrew. I had no job and few Chicago contacts save for a recently-married ex-girlfriend.

I remember weeping on the drive that afternoon while listening to Switchfoot’s I Dare You to Move:

Welcome to the fallout Welcome to resistance The tension is here Tension is here Between who you are and who you could be Between how it is and how it should be

I dare you to move I dare you to move I dare you to lift yourself lift yourself right up off the floor I dare you to move I dare you to move Like today never happened Today never happened before

I remember telling myself, “Never again.” This was a new start. I wasn’t going to fall back into the same tar pit that I had fallen into at school, and then again back at home.

I met William at his home in Humboldt Park – many blocks on the wrong side of Western. Instead of a lease, he gave me a legal pad and said, “Can you write, ‘I will give William $400 per month and stay in the apartment for at least three months”? I wrote a check for first month’s rent, plus another $400 for security deposit.

William noticed that I was wearing sandals on this chilly March day. He asked “Where are your socks?” I smirked and told him that I had long ago run out clean ones. He reached into his dresser and said, “I give you socks.” There was no point in arguing. I wore that pair for the next week. He asked if I had a bed. I told him I didn’t. He gave me his spare futon mattress.

I remember having a small bout of panic as I drove to my apartment. I remember asking myself, “What did I just do?” I reminded myself that, worst case scenario, I end up back where I was yesterday. Looking back, I’m not sure that was an accurate assessment.

I drove back to 2321 and met my three roommates. August was a law student who taught classical guitar on the side. Mike was a die-hard WhiteSox fan (they’d win the Series later that year) who grew up in Bridgeport, waited tables at the ESPN Club and, like me, had gone through the Walt Disney World College Program. Marty, a massage therapist, was a decade older and wiser than any of us and spent a lot of time secluded in his room, smoking cigarettes, drinking Old Styles that he chilled outside his window sill, and watching Telemundo on his 13” TV to improve his Spanish.

Before retiring for the evening, we all climbed the rickety ladder to the roof – the most redeeming aspect of the building – to stare at the skyline and smoke a little weed from a one-hitter. I had smoked weed maybe three times prior to that. It soon became a daily habit for the next few years.

That was March 22nd.

At 6:30am on March 23rd, I woke up from my futon mattress on the floor. The sunshine, so bright, spilled in through the undressed window, crept across the hardwood, and fell over my eyes.

I asked myself, “What am I going to do today?”

“Anything I want.”

“What am I going to do for the rest of my life?”

“Anything I want.”

I didn’t go to college because I wanted to. I went because that’s what you’re supposed to do. I didn’t move back home because I wanted to. I moved back home because I had nowhere else to go. Until that morning, my life had been, at most, minor deviations from a path largely decided by circumstance and the expectations of others. Moving to Chicago was the first time that I had swum against the current.

I wrote this in my journal:

I was reborn in Chicago. I became a man in Chicago. I have been forged by Chicago. This great city has, indeed, given me opportunities to figure out what I want to do with my life. Opportunities that I never would have had back home. This great city has given me a wife, a daughter, a best-man, friends of all backgrounds and professions, a dream career, and more rich experiences that my ever-foggier memory can recall.

I celebrate March 23rd as if it were my birthday. In many ways, it is.



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