Paint by Numbers vs Blank Canvas Careers
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 somewhat hilarious, somewhat troubling mistake as I sat around 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 bet it was in 1823.) Plaques on benches and sidewalks commemorate people who were very important and famous at one point, they 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 writing. My rules.)
School gatherings pummel you with pomp and overflow with circumstance. (OH, the circumstance!) Songs about the college reference things that, if I'm being honest, I didn’t quite understand despite my very expensive degree in the exact language they were supposedly speaking. (Did they just say “azure” and “betwixt” in the same sentence? And wait, hold on, why is this elm tree important to sing about again?)
Trinity is old and beautiful ... and very eager to remind you.
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 found myself on crutches for most of the summer thanks to yet another ankle injury in my illustrious career as a runner and basketball player. Rather than dreaming of gorgeous green quads and prestigious people whose ranks I might someday join, I spent the summer before college crutching after my mom at Target as we shopped for supplies.
I really needed a confidence boost.
And then, as I hobbled around Target, I saw it: The Poster.
On a black and purple background, a serious-looking Homer Simpson sat on a motorcycle, wearing a black leather jacket and aviator sunglasses.
The words BORN TO RIDE ran across the bottom of the poster.
I immediately grabbed 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 an episode of The Simpsons.
JAY, YOU'VE NEVER WATCHED THE--I've never watched The Simpsons, no. It's fine. You'll get over it. Chill out.
I'd never watched an episode. Not-a-one. Nor did I have some strange love for the character Homer enough to buy a giant picture of his round yellow face. Yet that's exactly what I did. Why?
To fit in.
To convey an image of myself to others. See? I am cool and confident and part of the mainstream culture and please like me and be my friend Oh God please.
Blah.
The words "personal brand" had thankfully not entered the lexicon at that point, but I think we just witnessed a young Jay making a desperate attempt to build a personal brand. (Fun fact: "a desperate attempt to build a personal brand" is also known as "an attempt to build a personal brand.")
(Look, I have feelings about that damn phrase and the gross behaviors it creates.)
Anyway, I bought the Homer Simpson poster and plastered it on my dorm room wall. And since the two-person room was so small I could have lied down and touched both walls without stretching out my arms, a single poster on the wall was like 20% of the wall space. You couldn't miss it. I was practically screaming at others to notice it. To notice ME.
The move seems childish, but of course, we do something similar as fully grown professionals all the time.
* * *
Like Sweet Baby Jay, we often feel our emotions have been blended to bits by our jobs. We sprint, then run, then jog, then walk, then wheeze, then collapse and lurch ourselves barely over the finish line ... only to realize there's a new quarter, a new project, a new goal, a new deadline to meet or problem to solve. Sometimes, it's all we can do just to stagger to our feet again. It’s then that the voices in our head start to creep in: "Just settle. Just do it that old, boring, outdated way. Nobody would question it. Just cheat and hack and coerce your way into your audience’s lives. Forget about service. Forget about craft. Forget about the hard but meaningful work. Take yourself off the hook, take the easy way out, and just take, take, take, take because that's what business people DO to WIN."
In these moments, when we feel like we're just eking by, or else we really need a win or a confidence boost, it’s so tempting to do something dangerous: conform.
We try to send the message to others that we think, say, and do what they expect us to think, say, and do -- regardless of what our intuition is urging us to BE.
When I bought that poster, I remember, I knew exactly what I was doing. I was trying to seem like I was the kind of person others expected or would accept, despite who I actually was. The whole time, I knew I was doing that. Isn't that such a tragedy?
That poor, Sweet Baby Jay ... standing there, leaning against his crutches, wondering if he'd see his best friends from high school much at all again, hoping freshman year of college would be okay. That eight-pound, six-ounce Baby Jay, praying it would all work out in the end, needing something to grab onto. Why not grab a poster ... with a character he didn't care about ... from a show he never watched ... with a slogan that made no sense?
BORN TO RIDE? Not so much.
BORN TO FIT IN? It sure felt like it at the time.
I bought that poster for others, and I can tell you with confidence that I knew exactly what I was doing at that time. How can I be so sure? Because today, I'm constantly reminded of that damn poster and how it made me feel to buy it and hang it.
I'm reminded when I inflate the number of subscribers to my newsletter. (I say 3,000. It's 2,600. Now I'm stressed just writing this, because neither number seems good enough.) (And NOW I'm stressed because, wait Jay, aren't you the guy who talks about resonance over reach?)
I'm reminded whenever someone asks how my work is going. ("Great!" I say. "Insanely hard. Super lonely. Really tough to balance with two kids," I think.)
I'm reminded when my conviction in my ideas or my mission falters, or when I tweet something that sounds more like the meme of the moment than myself.
I'm reminded each and every time I show up in a way that is immediately trying to appeal to OTHERS, rather than in a way that's reflective of who I really am.
In those moments, I see that damn poster once again.
The thing is, I’m not building my career for others. I’m building it for myself.
Aren’t you?
Think about your own moments similar to mine.
Have you ever hyped something you knew wasn't worthy of that much shouting?
Have you ever pursued some kind of vanity metric despite knowing it wasn't actually impactful to your business?
Have you ever buried your personality quirks in order to assume the posture you thought others wanted from you?
Have you ever thought something was broken or bad or backwards about a company, an industry norm, an expert others seem to love, but you stuffed that down to pay lip service to how others felt instead? ("Oh, Douchey McTwitterthread? They're great! Yep! DEFINITELY. What a thought leader!")
Have you ever stood there ... in need of a win ... and maybe a bit more confidence ... and maybe a goddamn break from it all ... and so you showed up as someone other than your true self, just to get by?
Yeah.
Me too.
But I think there's good news for us, and for that innocent baby Jay. (I like to picture him wearing one of those tuxedo t-shirts.)
The good news is this: Great friends don’t care about the posters on your wall. They require your true self. Great work is the same way. It requires your true self. Your actual beliefs, coming through forcefully. Don't couch them. Your actual quirks, coming out from where they've been hiding. Don’t bury them.
Your work. Your way.
Your career. Your choice.
Your life. Your script.
* * *
At Trinity, I didn’t love the pomp and circumstance. I’m sure you already guessed that. While I understood why some might enjoy it, I found it stuffy and archaic and overly didactic. A symptom of an institution that was rapidly drifting further and further out of touch. All the trappings seemed to be visual (or musical) representations of the traditional career path so many alumni walked before me: graduate from college, work in finance, buy a boat, summer on Martha's Vineyard, wear lots of pastel Polo shirts, and forever talk loudly and proudly about your beloved alma mater.
(Singing drunkenly) "Ohhhh, beneath the azure sky and betwixt the winter and spring season, there sits an elm tree which matters for some reason..."
(Again, I wasn't paying TOTAL attention to the song.)
The well-worn career path was on offer, wrapped in a bow, handed to me upon arrival at Trinity.
CAREER IN A BOX. (Warning: Do not think outside of it.)
But what "one" is supposed to do is rarely what you are supposed to do. People around you -- even people similar to you -- are not YOU. However, finding out what path works best for you is squarely on your shoulders. It's on each of us. We're completely on the hook to figure it out and pursue it. Nobody else will do it for us. Nobody else is coming.
Maybe you really want to open the CAREER IN A BOX. After all, some people love working in finance or whatever career path their college often promoted to them. That's great! Do it with gusto.
Some people like knowing each step ahead of them. Fantastic! The important part is that you know that about yourself.
But while some people want a paint-by-numbers career straight from the box, it wasn’t for me. I worked for brands like Google and HubSpot — organizations someone like me is "supposed to" work for.
I was miserable.
I realized -- thanks in no small part to lots of thrashing in the wrong jobs in my 20s -- I want a blank canvas career instead of paint-by-numbers. And if I don't like how this painting starts to look, I'll just toss it aside and grab a new canvas.
Maybe you're part of a circle of loving friends who do exactly what you do, or maybe your loved ones don't exactly understand what your work. (That's me, as you might suspect. A description of my four closest friends and I sound like the setup to a bad joke. "A doctor, a lawyer, a teacher, an accountant, and a [whatever the hell Jay is] walk into a bar...")
Because you can't really use a single word to sum up my work, though I say "writer" most often.
"Whatever the hell Jay is."
What I "is" is me.
(I did it, Dad. I wrote the best sentence of my life.)
What I am... is me. It's all I can be. It's all I'll ever be. So I may as well stop lying to myself and get on with being it. They say "to each their own," so we each may as well own it. If you really love the pomp and circumstance, sing the song. If you really love The Simpsons, buy the poster. But do it for yourself, not someone else, and not because you were told it's what you're "supposed to do."
The expectations of others become crutches on which we lean when our confidence wavers. In moments of uncertainty or struggle, it's tempting to stuff down our quirks and our convictions and show up to work (or our dorm rooms) acting like someone else.
I regretted buying that poster the moment I bought it. I regretted hanging it on my wall the moment I hung it. I regret it all now, even still. But it wasn't until now that I really understood why I did all that. I did it because I was scared and trying to hide behind a version of a person I thought others would readily accept. I wanted people at school to like me, so I tried to come across as someone who had more traits that I assumed were likable.
In our work, when we want to succeed, we try to look or sound like we possess the traits or accomplishments or metrics of someone we assume others will view as successful. We start doing what others expect from us, rather than what we expect from ourselves.
I implore you, no matter how uncertain or scared or stressed you feel, don’t buy that poster. Don’t obsess over what someone like you is “supposed to do.” Obsess over what YOU are supposed to do. Figuring out what that is might be a lifelong pursuit, but it's well worth a lifetime to pursue it.
Know who you are. Know why you do this work.
It’s your room.
Decorate it however you want.
It’s your career.
Do it your way.