If you were to ask me ten years ago what I’d be doing now, it wouldn’t involve copywriting, public relations, and corporate reputations. Back then my future was communes, arts bacchanals, and late-night graffiti runs. But here I am; button-up shirts, dress boots, the word “executive” in my job title. And even though the white collar pays, I sometimes feel like a fraud. Like, every weekday from 9 to 5.

There’s no guidebook laying out the path from fringe culture to mainstream professionalism. Or how to find career success without sacrificing your values. Google is clueless for “Top ten ways for a counterculturalist to succeed in the modern workplace.” So that’s what I’m going to start doing with this blog: I’m going to write the guidebook.

I want to get good at my job, truly. I’ve had moderate success as an artist and low-level communications professional, but for the first time in my life, I found something I want to get good at, something I can grow in. And though my career is particular, I think the lessons are universal. I’ll talk about what I’m reading, what I’m learning, and how I’m learning it. I’ll talk about my successes and failures. I’ll talk about the dumb shit people say, and the smart shit you can do to fight it.

Learning how to be “professional” when you came up through counterculture is sort of like showing up at a black tie gala wearing nothing but a Sex Pistols shirt and a strap-on. You’d have a good Vine clip but after your seven seconds it’s back to stealing wi-fi from your upstairs neighbor and wiping coffee grounds from the day-old bagels behind Dunkin Donuts. Which I’ve done more recently than I’d like to admit.

In other words, when you’ve moved into the professional world outside the normal middle-class pipeline, it’s tough. Really tough. Like, tough enough to make you miss living paycheck-to-paycheck. Which isn’t easy, but at least it feels holy, especially when it complements your countercultural credos: art for art’s sake, blessed are the meek, and other platitudes.jpg.

While lots of people have no other option but paycheck living, a smart percentage of artists and other creatives—especially those with college degrees and above-average work training—choose this lifestyle on romantic principle. At least that’s what was doing (or thought I was doing, anyway).

But as I’ve cycled through various jobs, ranging from the shipping docks of a stuffed animal warehouse to myriad offices washed in yellow fluorescence, I started to realize my romanticism was largely a mask for my fear. Because, if I’m being honest, the grown-up world of business is Pretty. Fucking. Terrifying. And I say this as someone with two bachelor’s degrees, a master’s degree, a 401k, and a few good dress shirts.

This professional fear comes from an acute strain of Impostor Syndrome. As a nascent professional, I feel disingenuous more often than not. Partly because it’s also Pretty Fucking Terrifying to willfully let your ideas be challenged and changed. Especially if those ideas had a deep-rooted dogma opposed to any kind of mainstream habituation. As a teenager I took social cues from Karl Marx and Noam Chomsky, political cues from Adbusters and CrimethInc, and business cues from Black Flag and Minor Threat. Industry, infrastructure, finance, marketing, science, and commerce were nothing more than gated communities for the petite bourgeoisie (until I realized that even counterculture is a target market).

I’ll always be sympathetic to counterculture, but the ongoing conversation between it and the so-called mainstream has always polemical. When you come into these ideas as a teenager, it’s easy to become devout. And the longer you stay with your party, the harder it is to leave. Which is why many never do. But no matter what side you’re on, drawing such a hard line between Us and Them never helps with the long game. The more I learn, the more I realize that there are no sides in this game. Only positions and perspectives.

And lately, my perspective has been changing. For the first time ever, I’ve found something I want to get good at. Something that pays well. That I can build a career in. That I can learn from and gain influence in. That I can learn about and master. That I can use to actually help others. Some call it selling out. I call it growing up.

Growth doesn’t happen without some pain. And lately my pain has involved bringing my past ideas and beliefs to bear on my present “professional” goals. Some learn how to be professional from their parents. Others learn it from the system. And a few just have a knack. As a K-12 homeschooler with deeply religious parents, I grew up outside the system. Counterculture was my belief, identity, and eventually, a thin lifeline of small paychecks from low-level jobs barely keeping me on this side of student loan default.

In other words, I’m learning to be professional; to be “successful” in a practical sense. To bring my romanticism to bear on our culture of pragmatism, and to bring my pragmatism to bear on my idealism. How to preserve my values and fine new ones. And even how to build my skills, plan, and share.

And though I’m writing all of this as an informal documentary, I also know there are others out there like me, asking Google questions it can’t answer. I believe we can learn new things—even if they challenge our old ideas—and still preserve our humanity. So let’s get better, together.

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