Every Job I’ve Ever Had: McDonald’s, Hospital Housekeeper, Real Estate, Editing

Photo credit: Aranami, CC BY 2.0.

When I was 14, my dad drove me to our local McDonald’s and told me to fill out an application. You can work when you’re 14 in Michigan, and my dad pretty much hammered it into my skull that if I can be working then I should be working. It’s probably why I’ve been able to make it as a writer. The concept of not working is kind of a foreign one to me. As such, I’ve developed a deep distrust of those who’ve never had to work a low-wage job. See why below.


I started out as a cashier, eventually graduating to the drive-thru and, once I’d earned my stripes, the kitchen. This was in the late ’90s, when there wasn’t much pressure on fast food chains to regulate the quality of its food, so things were pretty lax. Everything was frozen, quality control was lacking, and policies were routinely implemented but not upheld. As such, the job served as something of a playground for my friends and me. We’d wear fake name tags, stage wrestling matches in the freezer, and, if the mood was right, make out in the basement break room. It probably doesn’t come as much of a surprise that I was never promoted in my three years there  —  management has never been an interest or a forte of mine  —  but I did meet several close friends there, as well as my first girlfriend.

All in all, though, I’m really grateful that my dad forced me to work there. Working in food service is humbling as hell and, despite its reputation, a strong way of reinforcing the basics of a work ethic. As much as I messed around, I made it my beeswax to get to work on time and finish any job that I started. The extra cash was nice, too. I used it to buy my first car.

Retail Associate

I was still at McDonald’s when I got a job at Eddie Bauer. I was sick of coming home with grease burns and longing to work somewhere where I wouldn’t be looked at like a total degenerate by the customers. Enter Eddie Bauer, literally the least cool store in the mall. Remember that South Park episode where they find a caveman and know it’s from the early ’90s because it’s wearing Eddie Bauer? That was pretty much the perception when I worked there.

Basically, I manned the register, helped people on the floor, and folded and folded and folded. Most days were tremendously dull and I passed time by counting down how long it would be until “Last Train to Clarksville” played on our corporate soundtrack, which looped every three hours. For at least a year I worked there on weekday evenings and at McDonald’s on weekends. I honestly have no clue why I did that. I had no freakin’ life. Really, I think my dad just groomed such a fear of unemployment in me that my mindset was that, when it came to jobs, the more the merrier.

Cashier (again)

I quit Eddie Bauer to work as a cashier at Sam’s Club the summer before I went to college. My buddy’s mom was the manager and the pay was several dollars more an hour than I had made at McDonald’s or Eddie Bauer. The days were long, the customers annoying, and the blue vests so, so ugly — but I worked alongside two of my best friends and saved more money than I’d ever saved before. Also, that free membership was a godsend.

Hospital Housekeeper

For two summers in college I lived with my parents and worked as a housekeeper at the hospital where my mom worked. This was a gross, nasty job, but it paid twice what I’d ever been paid before. I worked mostly with guys twice my age, some of whom were using the gig as a stop-gap after getting laid off at much more lucrative jobs. It was enlightening in that way; they loved having a kid around they could use to bounce their wisdom off. My fondest memories are of all of us sitting in the smoking tent  —  I didn’t smoke  —  trading stories as the moon rose and our shifts dwindled down.

My first summer I worked second shift (3:30 p.m. to midnight) and my second I worked first (7 a.m. to 3:30 p.m.), but both were equally gross. I lugged around garbage, baled cardboard, buffed floors, and tidied the lobby on a riding vacuum (by far the best job). We didn’t handle syringes, organs, or toxic waste or anything, but we saw plenty of it  —  blood, tissue, afterbirth, you name it  —  and occasionally had to lug around the biohazard bins in which they were packaged. One time the compactor broke and a backup dumpster was dropped in the middle of the loading zone. We had to carry hundreds of bags of garbage across the loading zone in 100-degree weather, tossing them up and into the dumpster as their contents dripped back down on us.

One day, a co-worker grabbed a garbage bag and stuck himself on a used needle. He ended up being hospitalized for a month.

I wrote a play about it all a few years later. It was a love story, weirdly.

I’ll always remember one of the older women asking why I smiled so much, and another answering, “He knows he won’t be here for the rest of his life.”

Transition Specialist

There’s a bullshit title. One summer I stayed in my college town to do theater but still needed a job. I ended up getting one at the local Walmart, who were hiring boatloads of people to help implement a new design strategy. Basically, we built shelves and display cases and moved products from one part of the store to another. It was the worst job I’ve ever had, and I literally just told you about lugging garbage in 100-degree weather. Everyone was miserable, and worked to ensure you also were miserable. I was there for two months, I think.

Cashier (AGAIN)

I got dumped right after I graduated college. It was an important relationship, having spanned multiple years and some major life changes I don’t need to get into, so I was completely and utterly despondent that summer. I was going to grad school in the fall, but Dad demanded I get a job anyway, which ultimately ended up being a good thing. I needed something to distract me from my broken heart and I needed money to fund my need for booze. The economy was in the toilet, however, and the only place that would hire me for the summer was a local grocery store, where I again manned a register. It was humiliating, being a college grad and all, so I pretty much kept my head down, writing story ideas on scraps of blank receipt paper.

In a way, it was this job more than any other that taught me to bury myself in work in times of distress. Getting out of bed and pulling into that parking lot every day was awful, but it’s better to be busy when you’re sad. If there’s one thing my dad’s emphasis on discipline taught me over the years, it’s that.

Also, I ended up buying a children’s book from the grocery store bargain bin that eventually inspired my favorite tattoo, so there’s that.

Box Office Manager

I sold tickets for my grad school’s theater. I was horrible at it. I told you, I’m not a good manager.

Theater Instructor

I taught several introductory theater classes in grad school. I was good at that. It was difficult, since my classes were often the first exposure a lot of students  —  many of whom came from low-income, inner-city families  —  had to theater or a critical approach to the arts. You can’t win over everybody, but watching particular students find inspiration in Shakespeare or Our Town was lovely. It wasn’t lovely enough to make want to navigate the hellscape that is professional academia, but I’m glad I did it.

Ticketing Assistant

The first job I got when I moved to Chicago was at Chicago Shakespeare Theatre. I was actually aiming for a position in education administration, but the economy was at its lowest point and everyone was working below their pay grade. Basically, I took ticket orders over the phone while navigating what is absolutely the most unnecessarily complicated ticketing software on the damn planet. I also worked the actual shows, which was much more pleasant. At the time, at least, I was still charmed by the gentle, intoxicating buzz of watching an audience prepare for live theater. I quit after six weeks, though. My boss was a nightmare, my coworkers were weirdly snobby, and the work was awful.

I got to hold their Tony Award, though, so that was cool.


As I struggled to figure out how to make sustainable income without having to retreat to the cash register, I found some early success as a playwright after getting commissioned by a major Chicago theater. It was dumb luck  —  I’d interviewed for another position at the theater and didn’t get it, but I intrigued the artistic director enough in our interviews that he came out to see a show I had self-produced, which led to the commission. I’ve never been able to make a living as a playwright (no playwright does, FYI), but it was around this time that I actually began making money off of my work. I’ve been lucky enough that it’s remained a somewhat steady source of side income over the last eight or nine years.

Education Intern

I liked teaching, but not academia, so I figured I might want to work in education within a theater. As a way into that field, I ended up interning at the Goodman Theatre, which was a thankless, but ultimately enriching experience. The pay was comically small considering the hours I put in, but I liked my boss and co-workers and got to work with a number of underfunded schools in the Chicago area. I also wrote and designed several of the study guides we put out, and even did so on a freelance basis now and then after the internship was over. They didn’t have a job for me when it was done, but nobody did. Jobs were unicorns back then. I also realized I didn’t really like education administration. I didn’t know what I liked.

Catering Driver

Did I mention nobody was hiring? I got a job as a caterer at an Italian restaurant my buddies worked at and I literally can’t think of a better way to a) familiarize one’s self with the streets of north, south, east, and westside Chicago and b) learn how to drive like a Chicagoan. One of my bosses was a cokehead and the other was a misogynistic bully who called me a “girly boy.” Hilariously, this is the only job I was fired from.

Group Sales and Communications Assistant

I got fired because I was also working part-time for a prominent Chicago dance company as a ticketing administrator with an emphasis on group sales. Here’s the thing, though: I had no clue how to do group sales and no desire to learn. All I wanted to do was write, and the higher-ups started letting me pen press releases and the occasional bit of marketing for them, which is why I’ve added the “communications assistant” bit up top (that was never an official title, but I earned it, damnit!). My direct boss didn’t like me doing all this writing for the company, as I was supposed to be selling group tickets, which I absolutely wasn’t doing. I think I quit right before she was going to fire me. I wouldn’t have blamed her. Ticketing was not my thing.

True story, though: This is where my freelance writing career actually began. After sending out a PR blast (another duty my boss hated that I had), I connected with the guy who ran Chicago’s Gaper’s Block webzine. Through that correspondence, I ended up becoming a contributor. It’s so weird, how we find our way into our eventual careers.

Faculty and Grader Coordinator

I quit the dance company because I got a temp job at the National Association of Realtors (gonna gloss over that one for brevity’s sake) that eventually led to a gig with the Institute of Real Estate Management (IREM). By this point I knew I didn’t want to work in arts administration. There’s no money in it and, despite what they’ll tell you, pretty much everyone is overworked and miserable. I just wanted a steady, unobtrusive job to keep me afloat as I wrote plays. And this job was perfect.

What is a faculty and grader coordinator? Well, basically, IREM worked to facilitate classes and testing for realtors working towards particular certifications. We also helped train realtors to become teachers in the field of real estate. My job was to work with those teachers to schedule who would teach what class, assist in the grading process, and complete a whole bunch of other duties that I can’t even remember anymore. Was it boring? Dear god, yes, but I worked with friends, never took my work home, and the boss I had there remains the best boss I’ve ever had.


I was only at IREM five or so months before I got the opportunity to basically “audition” to be a writer at Groupon. This was when Groupon was just getting popular and the NYT was publishing trend pieces about its creative writing staff — which meant that a lot of writers wanted to work for Groupon. It also helped that they weren’t looking for traditional copywriters, which was good for me since I didn’t have any traditional copywriting experience. They wanted creative people. I had to write three sample deals and do an interview, but I eventually got the job. They told us later that they only hired, like, 3 percent of the people who applied or something, so that was nice.

I wrote about spas and diners and laser hair removal and tanning and laptops. I wrote more bad jokes than you can imagine. We made a move into serving up supplementary content and started interviewing chefs and celebrities and musicians, and that was fun for a while. I did social media. I did trainings. I led “humor” and “voice” workshops. But mostly, I wrote — and most of that writing wasn’t the soul-crushing, corporate kind. In a broad sense, it was all I ever wanted out of a career.

I ended up being with the company for roughly five years, during which I watched it transform from disorganized millennial playground to business casual corporation. That’s not a criticism; it’s easy to rose-color the early “Wild West” days, but that shift was necessary for the company if it wanted to make sustainable cash. And it’s not as if the conditions were untenable when I left in late 2016; we still had a keg in the office. But the sense that us writers and editors served no real purpose anymore was beginning to weigh on me. It all began, really, soon after the company went public in late 2011. That’s when the copy got shorter, the jokes began falling by the wayside, and the ranks began disintegrating with no new hires to take their place.

Leaving was really hard for me, especially considering I did so to be a full-time freelancer, a decision about which my dad was none too thrilled. Giving up my vinyl habit was tough, too. But I had stayed far longer than I wanted to, mainly due to my devotion to the concept of steady, pleasant employment. I mean, I used to lug around biohazard bins.

Freelance Writer

Though I worked with Gaper’s Block and a few other small publications, I began freelancing in earnest when I linked up with Consequence of Sound through a mutual friend in 2013. In between my work at Groupon and my evenings writing and producing plays, I reviewed albums and concerts and festivals and penned articles about indie folk and pop punk. Working with them led me to The A.V. Club, with whom I’ve written about TV, film, music, podcasts, and just about everything else media-related. I worked with both for years before I felt comfortable relying on them for a steady income  —  it’s no secret that media companies aren’t rolling in dough  —  and though they both continue to serve as my main outlets, I also pad my pockets by writing for trade magazines and dabbling in sponsored content.

I’m still writing plays, too, but I’m very lucky in that I’ve channeled the passion I once had for them into my freelance work, which allows me its own kind of creativity. If not for that, and the fact that I haven’t stopped working since I was 14, I don’t think I could maintain the hustle.

Randall Colburn writes about music, film, TV, food, and podcasts for Consequence of Sound, The A.V. Club, Blumhouse.com, Splitsider, and more. Follow him on Twitter: @randallcolburn

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