A Story about Status and Freedom

I had a journalism career that lasted about two and a half years.

It began when I co-founded a monthly magazine my junior year of college called BLADU. The experience gave me something to focus my energy on, which was good, because most of my college life was dedicated to seeing how high I could get my blood-alcohol content on a budget of $70 a week (answer: pretty high). And running a magazine, even a sophomoric magazine full of typos, was no small task.

The magazine wasn’t great, but it wasn’t the worst thing to come out of the college, either. Some people read it. I know this because we got into trouble with the school’s administration, its fraternities, and nearly every organization on campus that took itself seriously every time a new issue came out.

One of our proudest moments was when we called the school’s president, whose name was Richard, “President Dick,” because he insisted that one of the school’s janitors call him “President [insert last name here].” Our school was tiny and informal. That kind of pretentiousness didn’t sit well with us. So we did our part to keep his ego in check.

The magazine gave me a voice I had never had before. I liked it.

I liked it enough that I decided I wanted to try to do it on a broader scale. So I applied to every magazine and newspaper that had an internship program, and I got rejected to them all, except for one.

The Zephyr was a weekly “alternative” newspaper run out the back of a Sav-A-Buk blinds store in Galesburg, Illinois. When I asked the editor of the paper, Norm Winick, if I could do an internship with him, he responded by email about a half a minute later telling me to come by the store next Tuesday at 5 pm.

That’s when he closed down the Sav-A-Buk blinds store and started editing. At 5 pm, only about 25% of the paper was usually ready to go. By around 11 pm or midnight, save a few crises, The Zephyr was done and ready to send to the printer.

There was no bureaucracy at The Zephyr. With only two to three dedicated staff, along with a few irregulars, things just got done. The process was to write, edit, and then submit. Errors got printed and imperfections happened. But our words made it into print every week, and a few people even read them.

My ambitions exceeded those of The Zephyr, so I leveraged my work at the alternative weekly into an internship at the local daily paper, the Galesburg Register-Mail. Unlike The Zephyr, the Register-Mail had a paid staff of editors and reporters, covering all the local things: high school basketball, Kiwanis club meetings, companies opening and closing.

In Galesburg, they were mostly closing. Though not technically in the rust belt, the term fits. Its population has been in steady decline over the last fifty years. Its economy was and is based on railroads and heavy industry and the late 90s were not a good time for either. It was a sad time in a sad town.

But working at the local daily was a decent job. There weren’t many paying jobs for educated people in Galesburg, so the editors and writers felt fortunate to be working there, even if the pay was terrible. As with all small-town newspapers, there was tension between the publishers and the editorial staff, and that bred a certain cynicism—something that was notably absent from my experience at The Zephyr. But the spirit in the newsroom was mostly positive.

This internship was the last semester of my senior year, and I didn’t want to spend the rest of my life in Galesburg. So I went looking for newspaper jobs around the country. I applied for jobs in Daytona, Florida, Sandusky, Ohio, and everywhere in between. The end of college came, and I did not get so much as a single interview.

Just as I was about to pack my car and leave for home, the journalism advisor on campus told me about a last-minute internship program at the Chicago Sun-Times. I applied, and somehow, got accepted for an interview. I put on my only clean button-up shirt, my Jerry Garcia tie, and my dad’s old sport coat and left for the big city.

The editor who was hiring for the position was a bit of an eccentric from Mississippi. He did not come from a privileged background, and so he gave negative weight in his hiring process to journalism students from prestigious masters programs at Northwestern and Columbia.

He planned to hire two interns based on a rigorous, three-hour long copy-editing test. He figured you couldn’t bullshit three hours of trap words like restaurateur, minuscule, and Filipino. After three hours of his test, he would know whether you had the chops to copy edit.

I took the test, and my score was the second best (he was very clear about the fact that the top score was much better than mine).[1] Much to my surprise (and as I later came to learn, the surprise of the other copy editors in the newsroom), I got the internship over the piles of masters students who were much more qualified.

I was over the moon; I was certain I had made it.

Chicago seemed impossibly big after four years living in Galesburg. And I was totally in over my head at the internship, and everyone around me knew it. But I learned a lot in a short time. My trajectory, from college magazine editor to Podunk alternative weekly, to small-town daily, to the Chicago Sun-Times, seemed only to direct me skyward. If I had managed this position at age 22, there was no limit to my career.

But after the first few weeks of excitement, I started to cop on to a very different kind of vibe around the newsroom. At the Register-Mail, most of the staff was looking to move on to better places. At the Sun-Times, many of the people working there were likely to be there for the rest of their career. It was a union paper, and it paid reasonably well. Most people who were there were there to stay.

Everyone was always friendly and kind to me, but the prevailing sentiment at the paper was a sense of bitterness. There was a deep disconnect in the vision of the paper that the staff wanted to create and what was actually being produced. Most of the editors and writers wanted to be serious journalists, producing something akin to the New York Times or the Washington Post. But most felt that what the publishers (then Conrad Black, who later spent time in jail for fraud and embezzlement) were driving for was tabloid trash and frivolous puff pieces.

I was having a great time and enjoying the ride. But everyone around me seemed cynical about what we were doing. There was no sense of pride or purpose. Way less so than the Register-Mail or The Zephyr.

This was not what I was expecting.

Still, my goal then was to be a professional writer. The editing was just something I did to get my foot in the door. So when an opportunity presented itself in the newsroom to cover the annual Jimmy Buffett concert, I couldn’t have been more thrilled. I didn’t know anything about Buffett and wasn’t a fan of his music, but it was an opportunity to get my first byline at the Sun-Times.

I drove out to the show, which was an hour outside of town, came back home at close to midnight, and then spent the night working on the review, which was due at 10 am the next morning. I didn’t sleep a minute, agonizing over every word. I didn’t know how many chances I’d have to write for the Sun-Times, so I wanted to prove with that first chance that I was worthy.

I’ll always remember my intro: “Jimmy Buffett was born on Christmas day in 1946, which makes sense, because for his legions of boozy and eager “Parrothead” fans, he might as well be the Messiah.”

But the next day, when I opened up the paper and read the first line of my review, instead it said: “Jimmy Buffett was born on Christmas day in 1946. For his legions of fans, his music is a gift.”

And so it went for nearly every sentence in the review. My name was there next to the article, but every bit of energy and personality I had tried to put into the article was gone. Nothing about the finished product was a reflection of me. I had published something that had made its way into a million homes, but it had ceased to be an act of self-expression.

I had moved up the career ladder going from The Zephyr to the Sun-Times, but at a cost of a total loss of autonomy. I wrote a few more articles in the next couple of months, but it was mostly the same thing. The only way to get published was to completely neuter what I had believed was interesting about what I was saying.

And so it was, six months after starting at the Sun-Times, I felt the sense of bitterness and cynicism that others felt working there. I could get published somewhere lots of people would read what I had to say, or I could write what I thought was interesting, but I couldn’t do both.


Norm Winick at The Zephyr died about seven years ago. And The Zephyr died with him.

But I’ve been thinking a lot about my experience there recently. Back then, as an ambitious 22-year-old, I thought I knew a thing or two about what I wanted to do and where I was going. About the way I’d be able to shape the world in my career. And I was wrong about almost all of it.

Back then, I thought that it was ridiculous that he ran the newspaper out of the back of a blinds store. Norm would have been hard-pressed to concoct a less prestigious facade for his media empire. But while most people on the surface would probably choose to work at the Sun-Times over an alternative weekly run out of the back of a discount window treatments store in Nowheresville, Illinois, nowadays, I’m not so sure.[2]

Status is nice. Getting recognition for what you do is wonderful. But it’s no replacement for having the ability to direct what you do in your work and in your life.[3]

There are some people who are lucky enough to have status and freedom. To do whatever they want and still get recognized for it. If you can pull that off, definitely do that. That sounds nice. But if you have to choose just one, to choose between status and freedom, the 40-year-old version of me is starting to think that maybe Norm was on to something at the Sav-A-Buk blinds store.

[1] Reading over this blog post after I published, I spotted at least a half dozen errors and inconsistencies. I’m clearly not that good of a copy editor.

[2] Daniel Pink in his book Drive talks about three principles that are usually present when people enjoy their work: Mastery, Autonomy, and Purpose. That’s all well in good, but as with most self-help books, it doesn’t provide much guidance in what to do when those aims are in tension. Life is all about the trade-offs. There was greater opportunity for mastery at the Sun-Times than at the Register-Mail or the Zephyr, but the autonomy and purpose were entirely absent.

[3] It’s a little too neat to say that I gave up on journalism when I noticed that I had to give up creative freedom just to make enough money to pay the rent. But that’s mostly true. In reality, I figured if I was going to spend the majority of my time and energy selling out, I might as well actually sell out in a way that makes decent money. And that’s when I decided to become a lawyer.