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How the biggest risk of my life paid off

On February 24 of this year, I left my job.

I wasn’t a casualty of the economy, and I wasn’t decamping for a better position (not immediately, at least). I left because I was worn out by a job I wasn’t suited for, in a line of work I didn’t want to pursue long-term. I left because months of trying to maneuver into a more satisfying role—either internally or externally—had come up empty, and because my existing role was a big reason behind that futility. I wasn’t learning the sort of skills I desired.

I was approaching my 30th birthday, with a resume that looked nothing like the person I wanted to be. And the longer I stuck around, the longer that ersatz resume got, the deeper that false impression sunk in. I needed to make a change. I needed to take a risk. Even if that meant giving up a steady, well-paying job and plunging into the lousiest labor market in years.

See, I wanted to be a writer. I don’t even mean I wanted to be a WRITER of Great and Important Works. I wasn’t deluding myself that I was Fitzgerald or Kafka, or even Barton Fink. I just wanted my job to involve writing, editing—generally shuffling around English words and the various dots and dashes and jauntily curved markings which keep ’em in line.

Plenty of businesses need copywriters, after all. With a little bit of background in journalism, an MBA, and (if I do say so) a decent proclivity for wordsmithery, I knew I could succeed in that line of work. Problem was, I didn’t have any way of proving it. Thus the decision to leave my job: instead of stagnating, I’d devote myself full time to building up a portfolio.

Not to bury the lede too much farther, but: It worked. Last week I started as a copywriter for Vodori, a web marketing and consulting agency right in my neighborhood of Lincoln Park. It took nine months, most of my savings, a good deal of hustling, a little luck, and more than one moment of sheer panic.

I’m not rambling on about all of this to boast. My hope is that I might be able to offer a kernel of hope and a few bits of advice to anyone who finds themselves grappling with a situation similar to how I spent most of 2011.

  • Do what you love: Suddenly unemployed and finding myself with a wee bit of spare time on my hands, I needed an outlet to start writing again on a regular basis—to shake off the rust and relearn some self-discipline. So I started up my TV criticism blog, The Vast Wasteland, under the aegis of the Chicago Now blog network.

I had no designs on becoming a professional critic (okay, it might’ve been in the back of my mind, but only as a long-shot). But through that I found professional contacts (as well as a slew of Twitter friends), and I sharpened my skills—all of which was a byproduct of simply writing for fun.

Lesson: do what you enjoy because you enjoy it, do it often, do it well. Sooner or later, someone may even pay you for it.

  • Actually, fuck it, do everything you possibly can: I revamped my blog. I printed up business cards. I got myself on the Groupon freelancer roster, contributing around 10 daily deal write-ups per week. I wrote local interest features. I joined a regular roundtable at StoryStudio, a terrific writers’ workshop. I signed up for temp work, and lucked into an ideal gig doing communications work at the American Medical Association. I was open to any and every opportunity for putting words on a page in exchange for a paycheck. And then one day, somehow, I had myself a decent little batch of clips.

(Oh, I also talked to a handful of companies that weren’t a good fit or whose potential for work fizzled out, enrolled with staffing firms I never heard from again, and sent out dozens of job applications that vanished in the ether. Sometimes it really is about throwing noodles at the wall.)

  • Just don’t try to do it alone: Remember that exposure I mentioned above? It paid off when a local publicist, Dana Kaye, contacted me about interviewing actress/author Amber Benson. I kept in touch with Dana, and that relationship eventually led (directly and indirectly) to other pieces and other freelance clients. I met another client through my StoryStudio workshops. At least half of my freelance output is attributable to knowing people who either had a gig or knew someone who did.

I hear many of you saying, “Ugh. Networking. IS THE WORST.” I agree. It doesn’t come easily to me in the slightest, but fuck all if it doesn’t work. Think of it like hitting the gym: You can hate the effort all you want, but it’s hard to argue with the results.

Granted, none of this is terribly original advice. Still, it bore fruit for me, and if nothing else you can rest assured that these clichés have become clichés for a reason: sometimes they work.

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