Adobe-full-color Adobe-white Adobe-black logo-white Adobe-full Adobe Behance arrow-down arrow-down 2 arrow-right arrow-right 2 Line Created with Sketch. close-tablet-03 close-tablet-05 comment dropdown-close dropdown-open facebook instagram linkedin rss search share twitter

Personal Growth

The Creative Conundrum: Pursue Your Art or Get a “Real Job”

Every creative has found themselves at the same career crossroads. One path leads where their heart desires. The other leads to "real" jobs. Mike Sager has stood there, and he reflects on why he dropped out of Georgetown Law School to live the creative life.

I could have been a lawyer.

I could have been a guy who wakes up early every morning and shaves and wears a tie and commutes; a guy with a regular pay check and cushy benefits who argues for a livinginstead of a guy who works at home in his sweats, filling blank pages with words.

This is what I remind myself. . .

Whenever another one of the countless story ideas I’ve submitted over the past forty years is unceremoniously rejected, “Thanks but no thanks.”

Whenever I’m chasing a client for a check—some multimillion-dollar corporation with a newsstand circ of ten million, which uses my work immediately but takes nine months to pay.

Whenever I’m making rushed, last minute changes to a story I finished months ago because the editor in chief has finally gotten around to reading it.  (They call this a top edit. I always wonder: Does that mean I’m the bottom?)

I could have been a lawyer. I could have been a lawyer. I could have been a lawyer. Instead of a guy who creates.


I guess I always wanted to be an artist. I suffered the early afflictions of being a kid who was loved too much. I felt special. I wanted other people to know. I figured out after a while that it isn’t enough just to tell them. You have to do something. You have to demonstrate. You have to create something that leaves an impression.

When I was in middle school, I thought it was music. I had long hair and a knockoff Les Paul electric guitar. I wrote songs and I sang.  I remember taking an aptitude test, bubbling in any choice that seemed to indicate my innate musicality. Some people said I was a pretty good lead guitarist. I definitely met more girls. But I couldn’t remember the chords to the songs—I had them written down in a notebook on top of my amp. Neither could I read nor transpose music very well—like spelling and remembering multiplication tables, the mathematical, memorization stuff just wouldn’t stick. And frankly, despite endless pleasant hours of practice, my fingers weren’t long or agile enough to spider along the fretboard and make the sounds I was hearing in my head. I wanted to be special, but no matter how hard I worked, this wasn’t my milieu. (Someone made that pretty clear when they unplugged my amp during a solo at the school talent show.)

In high school I channeled my creativity (and need for recognition) into sports. The expression of one’s artful self through physicality is not limited to dance. Anyone who has played or followed a sport knows about the grace of competitive movement. A drop step and strong move to the basket; a change of direction in the open field, a headfake, a perfectly-executed forearm smash into the corner.  I pushed myself as far as a 5-foot 3-inch, 135-pounder could go. 

Along the way there was a dalliance with photography. I had a good eye for composition. I even won an award in a contest sponsored by the local newspaper. But in those days, photography required a darkroom and a lot of trays full of smelly solutions. The deeper I got into it, the more it started to feel like chemistry. My brain and my heart couldn’t talk to my fingers without going through a whole lot of technical stuff.

And then, during my junior year of college, an older fraternity brother bequeathed to me the editorship of the college literary magazine. He was due to bring out an issue. Soon to graduate, he’d lost interest. If the budget weren’t spent, the money would revert to the university’s coffers. Gathering together a rag-tag bunch of friends, pulling together resources from the English department, my frat, and the newspaper, we brought together an issue.

The night of production remains a Technicolor blur. What I remember is being in the college’s newspaper offices with a room full of novices, each of us equipped with an X-Acto knife, as publishing dictated in those days. Nobody knew what we were doing. I spent the night going from person to person, working with each to solve this problem and that. It was frustrating and difficult, but it was glorious, too. All of us in a room together, stretching our creative muscles, working to make something from nothing. It felt like one of those old movies starring Mickey Rooney and Judy Garland—we were like neighborhood kids who’d decided to put on a musical. Singing and dancing to the music of our own creation, we committed art.

After that I was asked to join the newspaper. I became a columnist and an editor. Almost every night, during the hours after all of my frat brothers had gone to bed, I found myself sitting in a chair at the poker table in the living room, typing my latest piece.

In writing, I’d finally found an outlet for the creativity I wanted to express. My mother always said I was a good bullshitter. Maybe that talent served me well. At any rate, by using words, I found that I was able to say the things I wanted to say—although it would take many years before everything sounded on the page the way I heard it in my head.

More than anything, I loved the process of writing. I loved the building of words into sentences, sentences into paragraphs, and so on. I loved the rhythms and the sounds. I loved the revisions, killing your darlings to create better ones. Frankly, I loved everything about itplaying the keyboard, reading to myself in a low monotone that is not quite humming and not quite talking about loud. The keys go clicka clack. Twenty-six neutral symbols are willfully recombined. Text appears. It fills the page. And then the next. 

Over time, the accomplishment of output was my demonstration of self worth. Before me were the results of my creative being made whole. Nobody could argue with that.


You might wonder. If I loved writing so much, how did I end up in law school?

Having a profession to fall back on was my parent’s suggestion. It seemed like a logical plan. I had no clue how to become a writer, and nobody around me knew either. The play: Go to law school; get an important high-paying job; branch out into writing in my spare time, work up to making it a vocation. Surely it would be a way to distinguish myself from the hordes of other people who wanted to be writers, too.

Of course, this entailed actually having to show up at law school for three straight years.

I’ve never been good at doing things I don’t love, but I didn’t know this yet. I’d chosen law school not because I liked it or wanted to do it—I’d interned for a lawyer my junior year of college and loathed almost every minute—but because it seemed the mature course of action. I was now an adult, and that’s what adults did, right? Make a plan and stick with it no matter what.

I lasted three weeks.

More Posts by Mike Sager

Mike Sager is a bestselling author and award-winning journalist. A longtime writer-at-large for Esquire, he has been called “the Beat poet of American journalism, that rare reporter who can make literature out of shabby reality.” Since 2012 he has also been the publisher of The Sager Group, a consortium of multi-media artists and writers, with the intent of empowering those who make art.

Comments (19)
blog comments powered by Disqus

More articles on Personal Growth

Two pairs of hands playing a piano.
Illustration by the Project Twins