THE BLOG
07/04/2009 05:12 am ET | Updated May 25, 2011

Chicago For Dummies: What Our Newest Residents Can Expect

Summer's here, which means Chicago is filling up with young Midwestern college grads, looking for work and adventure.

I hope the lads and lasses aren't reading the Huffington Post for advice, but just in case they are, I have a cautionary tale to tell about the city as I found it when I was their age -- and as it found me.

I moved to Oak Park fresh out of Kent State University, back in 1992. The economy wasn't great then either, and so the adventure came easier than the work.

Especially as dumb as I was.

For instance, I assumed there were only two kinds of El trains: the To train, and the Fro train; boy, was I surprised when I got on what I thought was the Fro train but which turned out to be a third train entirely, headed for destinations unknown.

The trains proved to be a test of savvy that I failed again and again. Once on the Lake Street line I drunkenly lost my watch to a man in a shell game. Another time I became hopelessly and sheepishly stuck in an El-platform turnstile, with my golf clubs.

My attempts to find work also demanded more judgment than I had acquired.

I was shocked and frustrated by Chicago's disinterest in my shiny bachelor's degree in English. After being told by my advisor that I was one of the best poets at Kent State, I was turned down for a job at Bowler's Journal on Michigan Avenue because I didn't have much bowling experience.

Another interviewer for some kind of advertising job asked me, "How'd you like to make a million dollars this year?" I left, because I honestly did not want to make a million dollars that year.

I was initially grateful to land a minimum-wage job as the "night waterman," in charge of irrigating an area golf course from dusk until dawn. Night after night spent under what I remember to be a bare light bulb, staring into the slightly deranged eyes of my partner, a sad laid-off accountant, relief turned into horror. I didn't finish out the first week.

And then there was the "marketing" position that I interviewed for, out in a far west suburb. Dozens of interviewees and a five-minute interview during which it was ascertained that I had two eyes, a nose and a mouth. On the strength of those qualifications, I was told to report at 7:00 the next morning for an all-day "tryout" for the job.

The next morning I showed up in the only business attire I owned, an unfortunately chosen camel's hair coat my dad had bought me on my last day in Ohio. It was already 75 or 80 degrees.

I was introduced to the young marketing executive who would serve as my guide for the day. Hector greeted me warmly and asked for my help in packing cargo from a small warehouse into the back of his blue Ford Escort. Pink and light blue stuffed bears on this side, boxes full of black genuine plastic folders with built-in calculators on that. As we drove toward the city he didn't get into the secrets of marketing. He talked a lot about the power of positive thinking, the importance of never giving up, the need not to take no for an answer.

I was open to all of it, and listening so intently to my new marketing mentor that by the time he parked the car on a gritty street, we might as well have been in Memphis for all I knew. (Much later I would later learn we were in Berwyn, within walking distance of my apartment in Oak Park.)

Without ceremony, Hector opened the hatch and handed me an armful of stuffed bears and a box of the plastic folders. He took some bears and folders for himself and we headed into the first storefront we found open.

Barbershops, shoe stores, florists, taverns, gas stations, greasy spoons -- proprietors, customers, mail carriers happening along -- Hector tried first to sell them a bear, and if they weren't interested, he offered a folder. But often -- amazingly often, I thought -- they were interested. And many of them were interested in each of the disparate items. Three bears for my grandchildren -- two pink and one blue -- and a folder for my nephew. (Can I interest you in a unicycle?)

The early-morning boozers bought bears out of guilt, the frustrated young bowling-alley operator fed his ambition a folder.

Hector did all the marketing, I humped the stuff and learned.

By 11 a.m. it was 90 degrees. I was melting in that camel's hair jacket, and trying to figure out how I would break it to Hector that although I very much admired his positive attitude, I didn't think I was cut out for this work. I was too negative a guy, I told him over a hot dog and fries.

He seemed to take it well at first, but after lunch he pointed at a Dunkin' Donuts across the street from his car and coldly told me to wait there until he sold the rest of the carful. By now it had dawned on my Eliot Ness that this was some kind of pyramid scheme, and that Hector had lost out on a commission by failing to inspire me to become a marketing executive like him.

And I was sorry I had let him down.

But I still hadn't the foggiest idea where in Chicago's vast reaches I was, and I had no idea how I might find out. So I spent the afternoon staring hard at the blue Escort, needlessly afraid Hector would jump in and drive off, leaving me to fend for my utterly helpless self.

My summer-long festival of foolish trust and misplaced mistrust finally came to an end when, I found a job at a publisher named Ragan Communications, and went to work for a guy who understood naive young writers.

In a memoir, Larry Ragan wrote about his own first job. Just out of the service, in the middle of the post-war boom year of 1946, he went to work for the U.S. Dental Co., in the triangular Coyote building at North, Milwaukee and Damen.

"This company sold false teeth by mail," Ragan begins. "I worked there as a sales correspondent. There is no other way to put it: I was dumb. What blindness prevents us from avoiding such dumb decisions...."

Dear dummies: Welcome to Chicago. It's good to have you here.