The Simpsons Poster Mistake: A Lesson About Creativity as a Career
This article originally appeared in my weekly newsletter, Damn the Best Practices. Get one new story every Monday morning to be better than best practices. Subscribe here.
I went to college with a grand total of 2,200 students. That wasn’t my graduating class. That was the entire school.
During the summer before my freshman year, I made a stupid mistake just thinking about those 2,200 students.
Founded in 1823, Trinity College in Hartford lauds its history more than anyone has lauded anything since humans began lauding stuff. (I believe it was in 1823.) Plaques on benches and sidewalks commemorate people who were very important and famous at one point, we swear. Buildings that I can only describe as Hogwartsian surround the campus. (Okay, I can describe them in other ways. I just don’t want to. My newsletter. My rules.) School gatherings pummel you with pomp and overflow with circumstance. (Oh, what circumstance!) Songs about the college reference things that, if we’re being honest, I didn’t quite understand. (Did they just say “azure” and “betwixt” in the same sentence? And, wait, so the elm tree is special because … reasons?) Trinity is old and beautiful and regal and likes to remind you as much.
Prior to my freshman year, my 18-year-old self didn’t care about any of that. I felt like I had been tossed into a Cuisinart of Emotions the moment I graduated high school. Things felt so … uncertain.
To make matters worse, my metaphorical unsure footing was met by a literal version. I was on crutches all summer long thanks to yet another ankle injury from the strain of basketball games and cross country meets. So rather than dreaming of gorgeous green quads and prestigious people whose ranks I might someday join, I spent the summer before college hobbling after my mom at Target and Home Depot. I really needed a confidence boost.
And then I saw it: The Poster. On a black and purple background, a serious-looking Homer Simpson sat on a motorcycle, dressed in a black leather jacket and aviators.
“Born to Ride” it said.
I immediately bought it. I planned to hang it in my dorm room, and that’s exactly what I did. The poster sat above my bed all year.
But here’s the thing: I’d never even watched The Simpsons. (“You never watched The Simpsons?!”) Nope. I bought the poster purely to project an image to others. I was cool and confident and part of the mainstream culture and Oh God please like me and be my friend Oh God please.
The behavior seems childish, and yet we do this all the time as fully grown makers and marketers. Like younger me, our brains often feel blended to bits from the emotions of our jobs, and we hobble towards the finish line of the latest big push. In moments where we can really use a boost of confidence, it’s so tempting to do or say whatever we feel others will like or accept. We try to project an image — an image of comformity. (I think this is where clickbait headlines went from a tactic used by a few annoying publications to ubiquitous nuisance. Many editors, feeling rather Cuisinarted themselves, removed their own sensibilities in their decisions in favor of whatever others say drives traffic.)
In moments of uncertainty, we often cling to best practices that have become the hallmarks of our profession because … reasons.
At the time I bought that poster, I think I knew what I was doing. I wasn’t buying it for me. I was buying it for others. Today, that poster has morphed. It’s the inflated numbers I cite when someone asks how many newsletter subscribers I have. (I say 2,000. It’s 1,700. And now I’m stressed…) It’s the big smile and the confident quip when someone asks how my client work is going. (“Great!” I say. “Hard … and lonely,” I think.) Just like I bought the poster for others, I’m giving answers about my career for others too.
But I’m not building my career for others. I’m building it for me. Aren’t you?
Think about your own moments like this. Ever oversell what you do or how you’re doing? Ever feel proud to know the latest trend or tactic experts are writing about? Ever bury your personality quirks or your true feelings about the industry or your true feelings about the latest project others seem keen on creating?
Blah. I get it. But that’s not where we should start our thinking process.
Great friends don’t care about the posters on your wall. They require your true self. Likewise, great work requires you to be fully present and engaged. As creators, we should start with what WE love building, who WE are, and what WE believe. Then and only then should we set about finding others who appreciate that and want that too. Finding that overlap is what a fulfilling career really is.
At Trinity, I didn’t love the pomp and circumstance. I’m sure you can guess that by now. I found it stuffy and archaic. It seemed to be the embodiment of the paths so many alumni had taken before me: work in finance, buy the boat, summer on the Vineyard, and talk constantly and proudly about your alma mater.
That’s what I was “supposed to do.” But I realized that the trappings of the school and the implied idea of a life well lived were merely options of “what works.” Sometimes people really do want the job in finance and the identity that’s defined by their college. Sometimes people really are big fans of the Simpsons.
Me? Not so much. In fact, not at all.
We love to laud the successes of the past, from old alumni to new entrepreneurs. However, when we do so, we tend to create a canon of the traits and tropes and tendencies required to find success. When we obsess over them, we often remove the self. We conflate what worked for others with what works for us. What others did in the past or what they expect of us today become crutches on which we lean when confidence wavers and we feel bruised and broken. As a result, we spent far less time trying to understand ourselves and how we might bring our core beliefs and traits to our work. Or our dorm rooms.
Buying and hanging that stupid poster is one of my biggest life regrets. The act itself wasn’t so bad so much as what it represented: my obsession with what others wanted from me rather than what I wanted from myself.
I implore you, no matter how uncertain you may feel in your work: Don’t buy that poster. Don’t obsess over what you’re supposed to do or say or believe because others declare that success looks a certain way.
Remember why you do the work you do. Remember why you like to create stuff in the first place.
It’s your room. Decorate it however you want.
It’s your career. Make it your own.
Founder of Unthinkable Media. Believer that exceptional work happens when you find and follow what makes you an exception. Ex-Google, HubSpot, NextView (VC). Speaks on stages and into microphones for a living. What a weird and wonderful life. #MakeShowsNotPieces