The Book of Jobs Part 3 was originally published in Reglar Wiglar #24.
This issue completes my decades-in-the-making “Jobs Trilogy” where I recount every job I have ever held regardless of the duration of said occupation. How does it all end? Does it end? Well, for the past year and a half I have been able to support myself full-time as a freelance writer. It was, after all, a writing degree I earned at Columbia College all those years ago.
If you’ve read the previous two issues, you know there were many food service, telemarketing, and miscellaneous bullshit jobs in between. Some lasted a few days, one lasted the better part of a decade.
What they all had in common, to a certain degree, is that they all sucked in many ways. Some much, much more than others. There’s a lot to get through, so let’s get to it, shall we?

Slingin’ Veggie Hash
I left fast food — excuse me, quick service food — behind in June of 1994 (see Part 2), but before I put in my two weeks’ notice at that nut asylum, I hit the pavement, Reader classifieds in hand. With a few years of restaurant experience under my belt, I thought I could get a job on the line somewhere. I headed to the vegetarian Chicago Diner on North Halsted Street.
Even though I had been gorging myself daily on Italian beef and sausages, mozz sticks, and hot dogs straight out of the pan, and animal fat was probably being secreted from my sweat glands, I was hired. I started my new job less than 12 hours after my last shift at Fazzio’s ended. There were many beers at Delilah’s with my now former co-workers in that short interval.
Before the Diner, I had never gone completely meatless for any length of time, but my eating habits changed as a result of working there. I felt healthier than I had in years, maybe ever. That dietary change has lasted going on three decades.
Tofu You
The job wasn’t all a bed of tofu, however. The line was stressful, the work hard, the personalities encountered abundantly challenging, the money lacking, and my living situation shitty.
On the plus side, during my three-year stint at the Diner, I published the Reglar Wiglar with regularity while also writing for a few local music magazines. I started a band with my coworkers (Team Satan) and made lifelong friends. There were some nights we stayed up until the sun came up, listening to and arguing about music, drinking beer, not sleeping, and still going to work the next day.
Even so, one day you wake up and, it’s not that you just can’t do it anymore, but you see that day coming and there’s no way to prevent it. After three years of “slinging veggie hash for the man,” it was time to move on. I did my usual routine of lining up the next gig, putting in notice, and hitting the bricks. I found a job as a line cook at The Dellwood Pickle in Andersonville not far from where I was living in Uptown.
In a Pickle
Contrary to what image the name might conjure up in your mind, the Dellwood Pickle was not a deli, it did not serve pickles, and it was not located in Dellwood as such a neighborhood does not exist in Chicago. That was just the name the original owners bestowed upon their restaurant. The Pickle was a small neighborhood storefront bistro popular with the locals in Andersonville. As an employee, the owner had bought the Pickle from her bosses.
I was hired to work the line, which was a six-burner stove with an attached flat top and a salamander grill. I cooked Alfredo sauce and pasta, blackened catfish, Ahi tuna, salmon, burgers, and chicken breasts. It was a fast-paced line and it felt good when it was hopping.
Pickled Pink
The Pickle opened for dinner at 5 p.m. six days a week and did brunch on Sunday mornings. It was a comfort knowing you would never be called in to work a lunch shift or to be scheduled on a Monday ever. It was well run and things rarely went off the rails. If you got in the weeds you didn’t stay there long. This was due to the constant, calming presence of an owner who never yelled or freaked out. She also took the staff on a field trip every summer to Great America or an Indiana water park or to play bingo in some church basement.
Of course, once I got three years in I was done. I dropped to part-time and took another part-time job at the Beat Kitchen in Roscoe Village where a couple of my bandmates and ex-Diner employees had relocated. I eventually dropped down to just the Sunday brunch shift. When brunch was over, I would ride my bike from Andersonville down to Roscoe Village, a distance of about four miles, and close the Beat Kitchen.
Inside the Box
One job I returned to a few times in the mid-90s was at Victory Gardens Theater in Lincoln Park. My sister was the general manager of this non-profit live theater and they occasionally needed help with subscription renewals, ticket sales, and data entry. I was highly unsuccessful at selling subscriptions, but I did sit in the box office for a few months in the fall of 1997.
The Always… Patsy Cline show moved to one of VG’s theater spaces that year. It was a very popular show and the box office could get pretty hectic. All phone lines would light up at once and stay that way for hours, requiring me to answer the phone with “Victory Gardens, please hold,” on down the queue, then return to the top to take ticket orders and enter them into a DOS-based software system. It was just another job in what was becoming a growing list of temporary part-time gigs.
Beat Kitchen
I worked at the Beat Kitchen for about six months in 1998. At the time, the owner was booking some of the worst bands in the city. The kitchen was adjacent to the music room, so not only was it bad, it was loud. Really loud. There were some characters in the kitchen too, of course. Like Bad Ronnie, for example. Bad Ronnie was a painter and white rapper from Detroit who would talk about his various art and music projects for the entirety of a shift, stopping only to retreat downstairs where he had a small bong hidden in the ceiling of the basement.
The BK was a good place to hang out after work. We played Lounge Ax in a highly amateur softball game, which we somehow managed to win. Both teams featured the most unathletic humans in the city at that time. I got a double which may have been the first hit of my life. Wilco’s Jeff Tweedy, who is married to Lounge Ax co-owner, Sue Miller, competed wearing an old-timey baseball uniform. Bad Ronnie made a kid cry by taking away his bat.
Shoveling Dough
The kitchen was very laid back. It never got really busy that I recall. I worked the pantry and pizza side and did a lot of prep work. There is a heartbreaking truth about the pizza cook. Once you have lovingly rolled out and shaped the dough, layered on the sauce and toppings, and slid the pizza shovel underneath, there is no greater feeling of defeat than seeing that pizza destroyed when the middle of the pie sticks to the shovel as you attempt to slide it in, thus sending the ingredients into the oven to quickly burn and churn out smoke. You think you’ve sprinkled enough cornmeal on there, but you haven’t. You haven’t.
After six months of working two restaurant jobs and being perpetually broke, I reached a breaking point. One night, while taking out a few heavy bags of dripping, disgusting garbage, I decided I had had enough of this stinking, freaking, bitchass restaurant business.
That’s Classified
The longest employment stint in my entire career was four months shy of eight years. Not only that but at 28 years old it was my first M-F, 9-5 gig. I wasn’t sure I could do it but I adjusted fairly quickly and soon adapted to the routine and appreciated the reliable paycheck. I was a Classified Ad Rep for the Chicago Reader—the weekly alternative newspaper I had used to find countless jobs and apartments. Never before had I perks like full medical and dental insurance, paid vacation and sick days, regular pay raises, year-end bonuses, profit sharing, et cetera.
The job enabled me to pay off my student loan many years early. I also no longer needed roommates to survive and got a sweet deal on a two-bedroom apartment in Logan Square. I turned one bedroom into an office where I published this zine and ran the RoosterCow record label.
Job Not Wanted
The downside: it was a customer service job with lots of time spent on the phone talking to dumb and/or angry people. It was also very repetitive. We dealt with Chicago’s many landlords and real estate companies/agents, employers of all stripes, and ran thousands of free ‘for sale’ and ‘wanted’ classified ads. And then there were the “adult services” advertisers about which I could devote an entire issue to, but probably won’t.
All in all, it was a good company to work for until the Internet decimated the newspaper industry and Craig’s List destroyed the classifieds gravy train with particular relish. After eight years, change was in the air and it wasn’t good. I got out before the paper sold (several times) and went into bankruptcy. A department that once staffed about a dozen people 12 years ago has now been reduced to one person, last time I checked.
Suck Co.
Remember my four-day stint on that river boat (RW#23)? I like to refer to that gig as the Second Worst Job I’ve Ever Had. My five weeks at an advertising agency trumped it due only to the duration of the ordeal. In 2006, I left the scruffy classified crew behind in an attempt to move up the ladder, or “sell out”, as it were.
I got a tip from a relative who had a friend who had a daughter who worked at the downtown ad agency I like to refer to as Suck Co. Through that connection, I was hired on as an editor, although I was basically a glorified proofreader with only one person under me; the actual proofreader.

Sad Man
Along with four production people, our team was tasked with creating a never-ending stream of newspaper ad inserts for a big box retailer. The client, who shall remain nameless, had recently gone through a management “shake-up”. They continually changed their style rules as well as the products they featured, as well as the price.
My average work day was from 8:30 a.m. to one or two the following morning. Mondays and Fridays I could expect to be out of there as early as 9:30 or 10 p.m. The amount of actual productive hours during a day was probably less than half of those 13- to 16- hour days. The rest of the time I spent in a semi-comatose state staring at my computer screen drinking several quarts of coffee per day in between horrible meals sourced by Suck Co. from some of the South Loop’s worst restaurants.
Suck Co. seemed to be a horribly managed company. One incident that I remember with particular amusement (but at the time, disgust) was a request from the Vice President of Who the Fuck Knows. One morning this VP sent an email to everyone on the very tired and overworked team asking that we list all the office supplies and equipment we used in the course of a day. The point of this I guess was… who the fuck knows?
Emergency Inventory
Having neither the time nor inclination to take inventory of staplers and paperclips on this particular day, I ignored the email. Later an intern-type person hand-delivered to me a copy of the email printed on very nice paper and inserted in a very fancy envelope. Why it was so important for this VP to know that I used a stapler, a computer, pens, pencils, and a calculator — and needed to know right now! — was beyond my comprehension. Three weeks in and I couldn’t take the lack of sleep, the bad restaurant food, and the total and complete absurdity of it all. I put in my two weeks’ notice. I had no clue where I would work next.
Unemployment
Yes, I took a plunge without a parachute, choosing instead to rely on good fortune and my own perceived craftiness to save me. As much as I looked forward to an extended vacation, it was too angst-ridden to be enjoyed for long. I filled out a lot of job applications and emailed a shit ton of résumés.
I don’t remember how many job interviews I went on. One employer whom I was lucky enough to get an interview (in a group interview with nine other prospective hires) informed us that he had received almost 500 responses to his ad. I realized my résumé is comprised of a creative writing degree and a lot of restaurant work. This did not leave me many options.
Thank Craig
I searched Craigslist every day. I was able to get a work-from-home job that I can now barely remember. It involved writing copy for a company that tried to get people to sign up for online for-profit college courses. It paid less than minimum wage, was very confusing, and also sucked in addition to that. I also helped a friend demo a two-flat he bought in East Garfield Park and did a stage at a restaurant in Wrigleyville.
A stage (pronounced staj) is a tryout or brief internship—basically a shift you work for free. It’s French. I did not go to culinary school, I just worked in a bunch of kitchens. I can follow recipes and do what I’m told.
Having never done a stage previously, and when asked to stage I had no idea what that meant but learned quickly. My arrival was an hour before dinner service at this particular place. I walked in and met the chef. He asked me to make a peach cobbler then disappeared leaving me alone in a messy kitchen with dirty pots and pans stacked high in the sink. I was confused as to what I was supposed to do. There was no recipe memorized. I had no idea how to find a single ingredient in this chaotic kitchen.
I went into the dining room looking for the chef only to find him sitting at the bar getting a neck massage from one of the servers. When I found out it would be only the two of us working in the kitchen that night, all my fight-or-flight senses started tingling and I booked it the hell out of there.
Lollapaloozer
After quitting Suck Co., so confident was I that a new job was directly around the corner, I was actually worried about not having enough time off to enjoy a bit of a vacation. Ha! The manager of the Virgin Megastore (old college friend and former roommate) hooked me up with a four-day task setting up and dismantling their pop-up store at the 2006 Lollapalooza.
It also involved using a golf cart to pick up bands and musicians from various backstage areas and driving them to Virgin’s autograph tent. They were long days and breaking down shelves and tents and packing up unsold product after four days in the hot sun was a task not completed until the early Monday morning hours. I also caught a case of what I called Lolla-fluenza—a weird viral chest cold thing that I probably contracted after being forced to use porta potties along with roughly 65,000 other disgusting humans.
I forget who most of the precious cargo was that I delivered safely to their destinations, but I do remember carting Common, Flaming Lips, Iron and Wine, Killing Hannah, Lady Sovereign, et cetera. When I woke up at some point that Monday, I was sick as a dog and officially unemployed.
Thai Lagoon
After being unemployed for two months, I took a job as a restaurant manager at a Thai restaurant in Wicker Park. I did not relish the thought of returning to the hospitality industry, nor did I relish the thought of managing a group of people I had never met. It was a challenge, to say the least.
My commute to work involved taking a bus at exactly the time three different high schools on Kimball Avenue let out. Being exposed daily to large groups of teenagers in a confined space is the only way to fully appreciate them.
I also found myself waiting tables at this new gig. First here and there to help out, then with increasing frequency. In addition to managerial duties and waiting, I was also a phone order taker, counterperson/food packer, host, cashier, busser, janitor, and occasional dishwasher. I did everything but cook.
Turn Heel
Waiting tables felt like a betrayal to my brothers and sisters in the back of the house, but that is what desperate times call for. Waiting money is much better than kitchen money. The drawback is, and this is huge, cooks do not have to deal directly with customers. There is a nice barrier there with the servers in the middle. Does this make the disparity in compensation fair? Maybe not, but it’s a tradeoff to be sure.
Three years in and I got my three-year itch right on schedule. I left to spend the summer of 2010 in Greektown, after which I returned to the Thai place for another three years strictly as a server, then eventually just to host, pack food, and take phone and counter orders. Eventually, the restaurant sold and new owners came in, but by that point, I had decided, after nearly a quarter century in Chicago, I needed to leave for a while. Quite possibly forever.
New Jacked City
During the summer of 2008, I got a job as a delivery driver for New City. Similar to newspapers across the country, New City had slimmed down considerably since the height of the weekly alternative heyday. I mostly did the University of Chicago route in Hyde Park but occasionally the West Loop route as well. That route included University Village, South Loop, Pilsen, and Chinatown — a huge pain in the ass during the evening rush hour.
I eventually got pretty efficient at the Hyde Park route. Every Wednesday morning I took the Kimball bus to the Blue Line train to the New City office on Chicago Avenue. I grabbed the keys to a beat-to-hell rental van, drove it to the printers where they forklifted a pallet or two of newspapers into the back and off I went down the expressway in a metal can with shitty brakes and several tons of newsprint sliding around the back.

The pay was low. The traffic, parking, and everything that goes along with it, sucked. Probably the worst day was getting my fully-loaded van towed while I ran into a Starbucks on Clybourn Ave. I was warned the previous week by a good citizen who informed me that a tow truck was always lurking nearby ready to rush in and tow cars from the one spot in the small parking lot that was designated ‘no parking’.
My cell phone was in the van so I used the phone of the bike repair shop adjacent to the lot to find out the van’s destination. The bike shop workers told me that vehicles got towed from that single spot all day long. It’s the perfect hustle and the kind of completely legal shakedown the city of Chicago approves of and models its own behavior on.
Going Greek
If ever there was a job I was completely committed to walking out on mid-shift, it was this summer gig waiting tables on the rooftop patio of a Greektown restaurant. It’s definitely a runner-up for Second Worst Job Ever, but it’s gonna have to be satisfied with its number three spot for now. This was mostly due to an insane manager who I’ll call Stavros, which was not his name.
I will spare you the tricks of the trade that management used to pinch pennies and fleece customers. I’ll focus instead on Stavros, whose hard-ass style had winnowed the wait and bus staff down to a skeleton crew by mid-July, forcing the survivors to work six and sometimes seven days a week.
Anger Issues
One of Stavros’ biggest freak-outs occurred after he returned from a trip to Greece that he insisted he did not want to take because, according to him, he does not take vacations. He was in an especially nasty mood this day. In his absence, the dining room manager, Kiki, filled in for him. Under her brief rooftop reign, she instructed the servers to quarter the lemons instead of halving them. When Stavros returned to an entire case of lemons cut in this fashion, he went berserk demanding an explanation. After I told him, ‘twas Kiki gave the order, he screamed the following sentence six inches from my face: “Kiki can tell you how to cut lemons WHEN SHE OPENS HER OWN RESTAURANT DOWN THE FUCKING STREET!”
Despite his anger issues, Stavros really could turn on the charm when he wanted to and customers loved him when he did. When he wasn’t “on” however, he looked like a sad, defeated man. Toward summer’s end, he asked me if I wanted to stay on and work in the dining room downstairs after the patio closed for the season. I was elated to tell him that I was already going back to my old job at the Thai place, which, thank Zeus I did.

Apocalypse Lao
In 2012 I moved to Wisconsin. I was maybe going to make good on my long-threatened move into a trailer in the woods. Madison is as far as I got. While still in Chicago, I took a bus north to interview for an inside sales job at one of the city’s many weekly newspapers.
I would not get that job, but I had brought some food service résumés with me just in case. On a walk around the east side neighborhood where I was staying, I spotted a help wanted sign in the window of a Southeast Asian restaurant. I dropped off a résumé, took a bus back to Chicago, and promptly forgot about it. A month later I got a call from the owner, took a bus north to interview, and was hired on the spot. Despite my experience, however, training lasted four weeks. Four weeks of a lot of work and no tips. Four weeks after six years of SE Asian restaurant experience — experience so recent that my last work day in Chicago was four days before my first work day in Madison.
Jack of All
Servers were required to not only wait tables, but simultaneously take phone and counter orders, pack food, seat customers, and bartenders, all for $3.25 per hour plus tips. One hundred percent of the takeout tips went to the kitchen as did ten percent of our waiting tips. This egalitarian approach meant a lot of work for everyone and not much money for anyone.
My short commute to work evened things out a bit. I could walk there in four minutes flat. After two years, a year earlier than my average of three, I was done. I left to work full-time on a temporary writing project, but returned about a year later to do deliveries on weekends. Being a delivery driver can be great — cruising around town listening to classic rock, away from the insanity back at the restaurant — it can also be the worst: traffic, wrong orders, food containers breaking mid-transit, customers who somehow manage to not answer the door for their delivery which happened more times than I ever could have imagined (cell phone died, was walking the dog, jumped in the shower, et cetera.)
The Install Crew
Art installer is a job title I never thought I’d have on my résumé, but the brother of a friend hooked me up with this job at a museum on State Street in downtown Madison. It was temporary full-time work for roughly three installs per year for each of the museum’s three galleries.
I slapped multiple coats of paint on walls floor to ceiling, loaded and unloaded crates from trucks, packed and unpacked valuable art under the watchful eyes of traveling registrars, dealt with the whims of temperamental artists, and drove a scissor lift into a wall more than once. Returning home each afternoon, I was tired and sore, sometimes bruised and battered. I had just enough time to soak in a hot bath before my shift at the restaurant began. Thankfully, the installs only lasted four to five weeks.
I usually did not attend the openings of the shows I worked on. I did not want to be in the company of civilians who had no idea about the sweating, bleeding, and cursing that went into the show. The few times I did attend, instead of looking at the art I focused instead on barely visible blemishes on the walls, tiny nails holes that didn’t get spackled, drops of dried paint on the floor that didn’t get scraped, and questioned the levelness of every hanging frame.

Fair in the Square
The museum also hosted an annual art fair in Capitol Square every summer. During this time, the install crew transforms into the ice crew and is tasked with delivering 20-pound bags of ice to ice caddies, as well as hot dogs, brats, buns, and condiments to the concession stands located at different spots around the square.
It’s a 45-hour workweek packed into three and a half days and it can be brutal in the hot summer sun. To help cope, we created a themed playlist to blast out of the rented pickup truck as the “Icy Bunch” pulled up to concession stands. Depending on the particular commodities on the truck, you might hear “Ice Ice Baby” by Vanilla Ice or Foreigner’s “Cold as Ice”. But also “First Bratwurst of Summer” by Those Darn Accordions, LMFAO’s “Hot Dog” and if you were lucky, “Hot Cross Buns” sung by a creepy children’s choir.

Let’s Do Brunch
After quitting the Lao place, I worked on a writing project creating descriptions for every bike trail in the state of Wisconsin. It was temporary, only lasting about a month, after which I still had a collection of low-paying writing gigs and my installs at the museum about three times a year. I felt a little vulnerable financially.
While perusing Craig’s List one day, I spied an ad for a brunch cook at a vegetarian restaurant a few blocks away from my apartment in the Schenk-Atwood neighborhood on the city’s east side. I sent an email to the address listed in the ad detailing my restaurant experience and was hired sight unseen. I worked as a brunch cook mainly, but also as a sub for when other cooks didn’t feel like showing up. Of course, knowing that there was someone to cover for them increased the frequency of these occurrences.

Coincidentally, the restaurant occupied the former space of a dive bar my band had played at roughly ten years earlier. It was called Mr. Blue’s Anchor Inn then. It was also nearly 20 years to the month that I started at the veggie Chicago Diner (see above) and it was staffed by a similar batch of twenty-somethings, many of whom were working through hangovers. And just like old days, the work was hard and the pay low. After six months, when the cook I replaced wanted his old shift back, I gave it up gladly.
Freelance = Freedom?
Since 1993, I had been writing things that were published somewhere on a semi-regular basis. I also created most of the content for 20 issues of this zine, interviewed and wrote articles for the Illinois Entertainer, rock show reviews for the Chicago Tribune, and concert listings and venue reviews for websites (remember CitySearch?).
Since the Internet has killed many once-decent-paying writing jobs, I have taken every ridiculous writing gig you could imagine. I’ve been “passionate” about every boring subject conceivable sometimes for less than two cents per word. I have written reviews for products I’ve never tried (that’s most product reviews people — skip the 5-star reviews and go to the 1-stars, those are the only real ones).
Down on the Content Farm
I’ve written for content farms and writers’ mills and cranked out product descriptions, trivia questions, apartment ads, and blog posts for roofing contractors, dentists, and stamp collectors. I’ve been seriously underpaid to write e-books with assigned titles such as Strength Training For Fat Loss: Little Known Secrets For Muscle Building and Fat Burning. I churned out press releases for a PR company in L.A. that ended up paying less than McDonald’s when you factor in the time versus pay. I’m past that now, but it has been a struggle.
Freelancing is a hustle, simple and plain. Now I write about the retail produce and deli industries and blog about Chevys, Mazdas, and Toyotas, even though I’ve never owned a car.
The best part, however, is that I work from home. There are no obnoxious coworkers to tolerate, no long commutes, no soul-sapping drudgery. I set my own hours and two-hour lunch breaks are routine. I am a slave to deadlines, but I’m used to that now. Deadlines are how shit gets done.
I don’t know if I’ll ever work for someone else again, but who knows, I might even be back in the restaurant industry someday. Wouldn’t that be a kick in the huevos? Surely it would.
This Concludes the Book of Jobs
Did you miss parts 1 and 2 of the Book of Jobs? Start here.