Now that I had a place to live, the next logical step was to find gainful employment. I combed the want-ads in the morning paper, hoping to find a position as a bartender. I had some bartending experience under my belt—those two summers that I’d spend frowning behind the bar at the seafood restaurant while reading Russian novels and begrudgingly serving $1.25 drafts to old drunks. And I owned a copy of Mr. Boston’s Official Bartender’s & Party Guide, a small, crimson colored book that was bound in what appeared to be the hide of a defeated hellhound. The book taught me the difference between dry and sweet vermouth. It taught me how to make Slow Comfortable Screws, Cape Cods, Manhattans, and Tokyo Teas. I was the greatest bartender in the world, as long as I had the MBOBPG with me.

As I got dressed in my sharp, can’t-miss bartender outfit—white Oxford shirt with the sleeves rolled to the elbows, topped with an unbuttoned suit vest—I imagined that a rumor was already circulating about me through the Chicago bar and nightclub scene, that people were talking about me and my bartending skills. “I hear this guy can make anything,” one fictional nightclub owner said to another fictional nightclub owner. “He’s like the Jesus of bartending. He waves his fingers around, and poof, it’s ambrosia time.”

“He was down in the minors the last couple of years,” the second fictional nightclub owner responded, “bartending in some backwater town in upstate New York, squandering his talents. What a shame. But he’s here now. This kid, I’m telling you, is ready for the big time. Chicago is lucky to have him.”

I tucked the MBOBPG into my back pocket and headed off for my first round of interviews with the words “Chicago is lucky to have him” running through my head.

A manager at a bar on Division Street told me that, sure, I had experience, but I didn’t have any “Chicago experience.” This was the third time a manager had informed me that “Chicago experience” was a necessity for getting hired. “You won’t find anything in Chicago, at least not anything in a respectable place of business, unless you have Chicago experience,” she said. I asked her to please tell me how one gets Chicago experience in a city where no one will hire you unless you have Chicago experience. “Now that’s the million-dollar question—am I right?” she said. She promised to keep my resume on file, which I eventually would come to realize is the Midwesterner’s polite way of saying, “Please leave now and never come back.”

The next day I found an ad for an upscale oyster bar that was opening on Michigan Avenue. “Are You A Bartending Superstar? Then You Could Work For Us!” I phoned the number in the ad and spoke with a man named Tad. He told me to be at the restaurant at 3 p.m. on Thursday. Because I was still woefully green when it came to the Chicago Public Transit System, I boarded an uptown bus instead of a downtown bus and wound up arriving 20 minutes late for my interview. I walked into the still-under-construction restaurant and found Tad. He wore a Pee Wee Herman suit and frowned at me over the top of a clipboard. “Do you see these other people?” He pointed to a group of men who, to my great disappointment, all appeared to be taller and better dressed than I was. “These people were here on time today,” he said, somehow yelling and whispering at the same time.

Tad told me that I had two options at this point. I could leave now, or I could wait until they’d interviewed everyone else. Then, depending on their mood, they might consider interviewing the guy who showed up 20 minutes late and obviously wasn’t serious enough about this job to get there on time. “But I’m not making any promises,” he said.

Tad expected me to blow my stack and leave in a huff. I wouldn’t give him the satisfaction. Instead, I’d call Tad’s bluff and wait out the storm. I’d show him how tenacious I could be. I’d sit down, shut up, and not make any excuses for myself. Then, when I got my chance, I’d dazzle Tad and his fellow managers with my engaging personality and my bartending skills. I’d do something bold, like ask them if I could fix a round of Tokyo Teas (the recipe for which I would have to discreetly look up in the MBOBPG) from behind the still half-finished bar. “Poof, it’s ambrosia time,” I’d say as I delivered the drinks. (While lost on the bus earlier, I’d decided that “poof, it’s ambrosia time” would be my bartending catchphrase.) I was an underdog in this situation, which was fine by me, because I loved being the underdog more than anything in the world. “Count me out at your own risk, Tad,” I thought. “Count me out and it’ll be your damn funeral.”

I shot Tad several defiant looks across the room, which he may or may not have received. Then I waded into the milling group of my rivals. Up close, these people were even more attractive and put-together than they were from a distance. It was as if the menswear section of the JC Penny catalogue had come to life all around me. Two construction workers carried a large mirror into the room and leaned it against the far wall. I could see my reflection in the mirror. In the middle of this group of put-together, handsome men, I spotted a simian-like being wearing a can’t-miss vest-shirt combo that I was horrified to recognize as myself. The expression on my face wasn’t one of defiance, as I’d intended it to be. Instead, I looked angry and pale and desperate.

It was then that I felt the full weight of the futility of it all. I needed to find a job, sure, but I recognized this for what it was: a losing proposition. In the end, I did what Tad had expected me to do all along: I left. I’d lasted all of 10 minutes. I walked out of the half-finished restaurant, horrified that Tad’s told-you-so eyes were watching me go, and even more horrified when I realized that Tad probably wasn’t looking at me at all.

The next day I found an ad looking for bartenders of all skill levels to work at “Chicago’s hottest new nightclub” which was slated to open in Lincoln Park. This time I managed to get on the right city bus. When I arrived I was ushered into a small, darkened auditorium and was instructed to find a seat. Others filed in and filled the seats around me. A few minutes later, a bald man with a goatee took the stage. A headset-microphone apparatus sat on the side of his head like an exotic bug. He bid us all a good morning, then told us that coffee and danish would be served after a brief demonstration. “First things first. Who’s hungover this morning? Come on, let’s see the hands,” he asked playfully. I was, in truth, slightly hungover after having picked up a six-pack on the way home after my oyster bar debacle from the previous day. Maybe a few days earlier I would have fallen for this man’s trick. But I was becoming savvier and more cynical. I was getting more adept at spotting traps and pitfalls before I stepped into them. The few people who were bold enough to raise their hands and titter, as far as I was concerned, might as well have held up signs with the words “DO NOT HIRE ME—I AM A DRUNK” painted on them. I kept my hand down, where it belonged, and rolled my eyes in the direction of all the hand-raisers. “Fools,” I thought.

The goateed man, to my surprise, began juggling a bottle of liquor exactly like Tom Cruise does in the 1988 movie Cocktail. “In the sexy world of restaurants and bars, no one is more powerful than the bartender, am I right?” the man said. He skillfully grabbed a second bottle and tossed it into the air. Now he was juggling two bottles simultaneously. “The bartender is the one who keeps the good times flowing all night long. Am I right? He’s the one who knows everything and sees everything. He’s the oracle of good times. He’s the keeper of the fun.” At this moment, to punctuate the word “fun,” both bottles simultaneously came to abrupt halts in his hands, both necks facing downward. Dual liquor streams coursed into the glass in front of him. A couple of people broke into polite applause.

I realized in this moment that I had been duped, that I had fallen into the biggest trap yet. There wasn’t any new nightclub opening in Lincoln Park. I recognized this for what it was: an underhanded way to coerce vulnerable people into taking a two week $199 bartending course. A woman began distributing pamphlets to the audience. “Walk into any bar or nightclub with a degree from the Royalton Bartending Academy, and you’ll get your dream job—we guarantee it,” the bald man said. A dozen people promptly got up and left. I was about to join them when the man said something that sent a chill up my back and made me sit back down. “Have you ever been told during interviews that you lack ‘Chicago experience’? That has to be frustrating—am I right? Well, a degree from Royalton Bartending Academy is exactly the type of ‘Chicago experience’ your future employers are looking for.”

That’s when I noticed the names of several bars that I’d interviewed at earlier in the week, including the one on Division Street, listed as “patrons of the Royalton Bartending Academy” on the back of the pamphlet in front of me. All the wind went out of me.

I eventually pulled myself together and vacated the premises. Though I’d been tempted for a few weak moments, I still had too much stubborn pride to sign up for the $199 Royalton Bartending Academy course. On the way home, I walked by a videogame store. Feeling doomed and unable to control myself, I purchased a copy of Contra III: Alien Wars for the Super Nintendo for $69.99. I had no money, and should have been spending every waking moment trying to find work instead of playing videogames. Yet, here I was self-destructing in the dumbest, most predictable way imaginable. I went home and drank a six-pack and played the game until I fell asleep on my futon with the controller in my hand.

I no doubt hoped to wake up back in my own bed, back in my old room back in my parents’ house, exactly like Dorothy does at the end of The Wizard Of Oz. I’d wake up to the sounds of my father building a fire in the wood stove—the crumpling of the paper, the roar as the match made everything go up in flames. But the next morning, as soon as I opened my eyes, Whitney Houston was telling me from a neighboring apartment that she would always love me. And I knew, right away, that I was a long way from home.