The summer of 2005 was a fine time to be 26 and an even finer time to have a dream. All around me, people were going big by purchasing homes or committing as heavily as they could to can’t-miss ventures or, in a lot of cases, reinventing themselves entirely: friends and colleagues were moving into two-, three- and four-bedroom “smart investments” all across Chicagoland while locked in an arms race with people “chasing the dream” in oddball lines of work to see who could “live more fully.” I, wise young man that I was, set my heart on joining the ranks of the latter.
My university mandated that I declare a major during my sophomore year of college, as though any 18- or 19-year-old has any real idea of what he or she wants to do with his or her life, or even what can be done with such a thing to begin with. In my case, it was simple: computers are easy and pay well, while writing is hard and generally does not. The Business Computer Systems program seemed like something I’d have been stupid not to go into, and I stand by that, but five years into the post-collegiate workplace the low effort and good money weren’t what they once seemed.
It’s funny to think about, considering all that has happened to the industry since, but this was also an exciting time in the media industry. Technology had arrived, yes, but there was still a sense of exploration to it; companies were thinking of their adaptation to these new tools and platforms in terms of bumps in the road, not enterprise-altering sinkholes. There was still so much promise. So much potential. So much opportunity. But that was all so, so very long ago.
GRE Study Guide: $30
As I still enjoyed the luxuries of being young and untethered, still free to roll the dice on a big move, I decided I would break the shackles of corporate life. No longer would I be Andrew Reilly, Systems Analyst but instead Andrew Reilly, Writer. What kind of writer, I would figure out later. “Travel writer, probably” was a fairly common answer of mine, as though that were the easiest way in the world to make a living.
Financially, this seemed like a good moment for a leap of faith. I had about two years’ worth of living expenses sitting in the bank and my only real liability—the $10,000 I still owed on my bachelor’s degree (I am still shaking my head over this)—would be deferred while I was back in school; on the more ethereal side of the ledger, there was also plenty of inspiration and motivation to be found in the platitudes of real-life acquaintances and online strangers. (It is amazing what miracles the confirmation bias will work for us when we need it to.) I would quit my job, go back to school full-time, get a master’s degree in journalism and get to work chronicling the world (or sports, or ￼music, or whatever, you know, I’d figure it out later) the way I was so sure it needed me to. Until then, I could survive: I grew up poor, so being broke would be a piece of cake, right? This was how it was done, right? First school, then skills, then the job: simple, right?
GRE Exam: $100
I forget how I scored, but I do remember taking the day off of work to take the test. That night, my beloved White Sox won the World Series for the first and perhaps last time in my life, and the next day I had to battle my way through arguably the most hungover Thursday any cubicle jockey has ever experienced. Totally awesome. Totally worth it.
Grad School Applications: $200 plus $1.40
Thinking I would be well-served learning a new craft or a new city, but not both at the same time, I decided to target a pair of journalism schools in Chicago. Yes, yes, New York was and remains the capitol of Where It’s At for the media industry, but Chicago had opportunities too, from the Old Guard Distinguished Paper to the Scrappy Neighborhood Justice Bulletins to the Respected Alt-Weekly but, most of all, my then-favorite publication and semi-secret dream employer and its fancy loft office just north of downtown: The Esteemed Culture Publication. This, I thought, was worth sticking around to pursue.
The extra $1.40 was to cover postage on letters of recommendation from a pair of former managers (that said, demanding payment for the right to be judged is a fucking scam, and I salute our institutions of higher learning for continuing to get away with it).
Two-Day Pass for the 2006 American Society Of Journalists And Authors Conference at the Grand Hyatt: $175 plus $150 for flight to New York City and another $125 per night in each of two very low-starred hotels in Manhattan (one night apiece)
I had been accepted into one (but not both) of those journalism programs but, for all my bluster and research, still hadn’t actually met anyone who made their living off of the written word, and it seemed wise to seek their advice—all I had to do was confirm these people actually existed.
Like an idiot, I didn’t reserve a hotel room in advance, but a supremely affordable place on 31st had a vacancy as I walked in off the street though, as I was informed repeatedly at check-in, “Just for one night.”
“Why only one night?” I asked.
The hotel clerk just shook his head. “There’s a conference in town,” he explained. “Bunch of writers up at the Grand Hyatt. I can get you into our other hotel tomorrow night—also for just one night. Same conference.” That I was competing with the supposed top of this profession for rooms in the both the cheapest and second-
￼cheapest hotels in Manhattan probably should have been a sign. But this was not a time for signs.
Unknown Number Of Drinks At My Going Away Party: $100 (maybe)
Yes, I got extremely intoxicated and yes, I made a complete ass of myself and yes, if you were about to start what you imagined would be an entirely new life you would have done the exact same thing.
New Laptop: $1,077
My old desktop PC probably had another year left in it but, let’s face it, those coffee shops and bars just weren’t going to write in themselves.
The M.A. program would only take three semesters if I went full-time. In hindsight, I consider this one of my luckier breaks.
CTA Fare One Resourceful Afternoon: $1.75 plus $0.25 for a transfer
By virtue of having been the first person to respond to their ad on Craigslist, I was “hired” as an editorial intern for the summer and fall at the Esteemed Culture Publication. (“Hired” is in quotes here because it didn’t pay, and because the interview itself consisted of three questions:
1. Why did you go back to school?
2. You know what, this is stupid. When can you start?
3. Why’d you wear a suit to interview here?
1. I just wanted a change of pace. ["Well, I hope it wasn’t for the money," the hiring editor added.]
2. Today’s Friday. How’s Monday?
3. Never hurts to overdress for an interview, I guess. [To which a different editor, who shared an office with the hiring editor, chimed in, "It can when you’re interviewing here." And yes, perhaps it also should have been a sign that two heads of a famous publication shared an office.]
But during my time with them, they gave me a free copy of their sister publication’s latest book, and some T-shirts, and an advance copy of the excellent Porcupine Tree album that came out that year, so in my view it all evened out.)
Anyway, one of the perks of my internship was the opportunity to contribute to a new section (“vertical,” to throw out some industry parlance) of the Esteemed Culture ￼Publication, garnering those precious bylines and clips along the way—and yes, I did agree with them that this was a “perk.” Clips, as far as I understood, were still the primary currency of the industry, even as actual currency was becoming less and less so.
For one particular feature they needed photographs of certain areas of Chicago. Would I be interested in shooting them and getting a photo credit in the print edition of the Esteemed Culture Publication? Yes. Yes I would.
Leaving the office I realized I had two dollars left on my CTA card and zero dollars in the budget above that for a few days, meaning the only smart route for this assignment was to take the L from the Esteemed Culture Publication’s office all the way to the end of the line, jump off and run like hell to the location, shoot away, run like even more hell back to the train station to beat the clock on the transfer window, then take the L all the way back downtown so I could transfer for free to a different line and ride out to the other location. When all was said and done, my editor commended me on the pictures, and to this day I still relish my copy of that print edition. But at the time, all I could think was I don’t know if this is rock bottom but it better pay off someday and also that here, in the height of a Chicago summer and five miles away from my neighborhood, it was going to be a long, long walk home.
Brake System For A Nissan Maxima: $1,100
I lived, worked, and went to school all in the city of Chicago. Why the hell did I still have my car? And why didn’t I think to drive it more than once every 10 weeks?
Additional Living Expenses: $10,000 (estimated)
Here’s the thing: that money I thought would last two years? It didn’t last two years. Not even close. Hello, second round of student loans.
Dry Cleaning, Early 2008: $10
There’s an old sci-fi trope about a man shopping for a bomb shelter who happens to be at the local hardware store/survival shop in his city’s bustling downtown, checking out the inside of this year’s model, when the bomb actually does go off outside, decimating civilization and leaving him stranded to ask out loud to no one at all, “Where is everybody?”
As a graduate student from 2006 to 2008, I had become that man: I had left behind a thriving world, finished on time, and emerged into the face of a demolished job market. It wasn’t just media that was hit, of course—but it was also especially media that was hit. So as I was sending off resumes and clips to anyone and any place that would read them, a Downtown Startup was also looking to hire a copywriter on contract for a few months. My only suit was wrinkled from a friend’s wedding a few weeks prior but something told me I really, really needed to look like an adult here.
Three Separate Lunches Eaten Quickly During Assorted Parts Of 2008, 2009, and 2010 Because I Had To Get Back To The Office: $30 (estimated)
The Esteemed Cultural Publication needed, at different times, an assistant editor, a copy editor, an associate editor, and a replacement for the local editor and I, having been freelancing for the Esteemed Cultural Publication for several years now, assumed on each occasion that the job was mine to lose and, on each occasion, was laughably wrong. We’re going in another direction, but would you still be interested in contributing? Yes, I said each time until finally, realizing mine would never be the direction in which they were headed, I said no.
I should add that, while it is small comfort that those positions, let alone that arm of the Esteemed Cultural Publication, no longer exist, it is actually somewhat more sobering that despite its massive readership, tremendous brand strength, and influence in any number of national conversations, not even the Esteemed Cultural Publication could expand its reach in the face of the new media economics. But this is the way things were headed, and to a large extent remains the way it is going.
Lunch That One Afternoon In July Of 2010: $9
The National Music Magazine I both read and respected needed a copy editor and by now I had clips, I had references, I had skills—this, as far as I was concerned, was a lock.
The hiring process consisted mainly of a joint interview with both editors, one of whom was a veritable encyclopedia of music and the other perhaps the most staggeringly beautiful woman with whom I have ever shared a conference table. Afterwards, on my way back to my “normal” job, I stopped in an excellent sandwich shop nearby for a turkey and swiss on a pretzel roll. Later I would be told I was “extremely overqualified” for the position, but they would love to bring me on as an unpaid contributor. Once again proving both my economic and professional savvy, I accepted their offer. The National Music Magazine has folded and re-launched twice in the time since.
Three Beers: $20 (including tip)
By the autumn of 2010 I was 31 years old and still very much in debt, and it was becoming clearer by the day that It Just Wasn’t Happening. Yes, the Esteemed Cultural Publication was just one outlet, but other opportunities were drying up around the city (and other cities, too). The Old Guard Distinguished Paper was wallowing in a bankruptcy nightmare from which it would eventually emerge, but only as a shell of its former self; The Respected Alt-Weekly was bought by The National Chain and later sold to our local Other Major Daily; the Neighborhood Justice Bulletins were largely shuttered—and let’s not even talk about what became of the Free Entertainment ￼Publications. For a while I had very seriously entertained the notion of chucking it all, moving to New York and rolling the dice one last time, but every time I looked at what I would need to pull that off without another job lined up and the possibility of starting over yet again, my tens of thousands of dollars of student loan debt just weighed me down even more—almost as much as the laughable cost of simply getting the keys to a New York apartment. (Seriously, I tip my hat to you New Yorkers for putting up with it.)
As a writer/software engineer friend of mine put it one evening after another 9-to-5 at our respective jobs, “You think I like programming? No, of course not. But how the fuck am I going to pay my rent with fiction and chapbooks?”
And there it was, my new moment of clarity: journalism had become the new poetry. It was adored but widely cheapened; valuable but largely unprofitable. Along the way, I had dug myself deeper into the hole and burned through essentially every dollar I had for what was at best a very worthwhile spiritual investment, at worst a very expensive vacation from adulthood. Maybe neither of those things. Maybe both.
In hindsight there are probably things I could have done differently. Move to New York for graduate school, or right after graduate school, or instead of going to graduate school.
Get better at schmoozing. Or budgeting. Be more aggressive.
Save up more money when I was 23 so I could afford to be broke further into my 30s. Research the industry’s prospects more thoroughly beforehand. Swallow my pride and work for a publication I didn’t want to work for. Or, alternately, don’t go into journalism in the first place. No shame in being a systems analyst.
But it is telling that among the group with whom I went through graduate school, almost everyone else has in their own way reached the same conclusion: Dana had moved to Chicago from Ohio to be a political reporter, and after graduate school went on to become a nurse; Lee had come in from Michigan with a bachelor’s in political science, semi-joking that after finishing up here he’d go for a doctorate in philosophy and “hit the trifecta of useless college degrees,” and the last anyone heard he was teaching English in South Korea; Karen went straight into corporate consulting and moved to Atlanta.
Of the 18 of us who went through that program together, only two currently work in media.
One could argue that my little excursion was just a reminder that some odds were never meant to be beaten, and that sometimes the real adventure is not in the journey, but in the detours and byways. One could also argue the whole endeavor—and countless others like it—was really just my way of postponing the inevitable, and that the arrogance and obliviousness of youth are no match for the wisdom only hard time in the real world can impart.
I wouldn’t disagree with either of those statements, at least not in any substantial manner, though I would posit that it could have been much, much worse. I ended up (eventually) in a very good job with excellent benefits that affords me the opportunity to live in a spacious, well-lit apartment in a great neighborhood in a major American city. Last fall, after years of perpetual calculation and some perhaps-too-aggressive checks made out to The Man, I finally paid off the entirety of my student loan debt.
But, most importantly, since first making that leap all those years ago, I have found myself involved in some creative and artistic endeavors that have paid intrinsic dividends worth far beyond what money can buy or measure, and along the way have also met and befriended some of the most interesting and inspiring people on the face of the earth.
Perhaps I didn’t end up with exactly the life or career I wanted, but I did end up with fine enough versions of those things just the same and that, ultimately, is the lesson that only time and experience can teach about anything worth chasing: first we dream, and then we wake. What happens in between will be what beckons, but what happens afterward will be what counts.
Andrew Reilly’s work has appeared in a number of fine publications. He lives in Chicago.
Photo provided by the author.