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Every so often, maybe six or so times a year, I get an email from someone asking if I’d be willing to talk to them about how to successfully leave academia.

While it is briefly flattering to think someone sees me as successful, and I’m always willing to have a conversation to try to help someone who needs it, I can’t say that I have any particular step-by-step plan of attack to offer. For one thing, I’ve never been entirely inside academia, so the difficulty of leaving behind something I’d specifically trained for, something I think more traditional academics struggle with mightily, was not part of my personal calculus.

But I do have some general advice rooted in some wisdom I received as a much younger man.

Many years ago, I was working as a paralegal for a massive Chicago-based law firm, a job I had no intention of staying in more than a year, but which I had been doing for 14 months. This failure to escape was causing me distress.

I conceived of three possible exits:

  1. To just give in and go to law school already. (What else was a guy with an English degree supposed to do?)
  2. To pursue a graduate degree in creative writing.
  3. To somehow get myself cast on season three of MTV’s The Real World.[1]

We had an administrative assistant within my work group who was 30 years my senior (or a little older than I am now) whom I gravitated to for advice, and whose insights about navigating the workplace and had proven invariably sensible. She had seen some stuff in her life, having emigrated as a young child from rural Mississippi to Chicago so her veteran father could take advantage of the GI Bill in ways that a Black man in Mississippi could not at the time.

She’d been at the firm for more than 30 years, starting there in the literal typing pool after finishing her associate degree, working her way up to a job with a supervising senior paralegal who was nice and fair and didn’t work anyone too hard.

The position I held, project assistant, was filled almost exclusively by the young and ambitious looking to bank some money and make connections before starting law school. There was a hierarchy based on whom you worked for, because the thought was a recommendation from a heavy hitter might carry some weight on a law school application.

Lots of project assistants worked late to demonstrate their preparation for the grind of being a lawyer at a top corporate law firm. I did it because after seven hours on the clock you were paid time and a half, and if you stayed past 7:30 p.m. you got a free taxi home and a $7 meal voucher.[2] Every hour we worked was billed to a client at a rate far above our cost, so no one at the firm was bothered in the slightest if we milked the system.

Unlike the project assistants, our administrative assistant left every day at 5 p.m. This was her top priority for work happiness. “Best job I ever had,” she once told me. “I got a life that isn’t here.”

As I told her about my various possibilities, she listened, bemused.

She asked if I wanted to be famous, or on TV, and I said “no,” so The Real World was dismissed as “nonsense,” which it was, independent of the impossible odds of getting cast on the show.[3]

She asked if I wanted to be a lawyer. I said, “Not really,” but that my dad and brother were lawyers and as we witnessed from the attorneys that surrounded us, it clearly paid well. [4] She asked me if I wanted to do what lawyers do.

“Hell, no,” I said. Certainly not those lawyers, anyway.

She asked about graduate school in creative writing. I said that I didn’t know if I could get in, but I had a professor who would probably help me and that I thought I might be good enough. She asked if I liked writing and I told her how that sometimes, when I was supposed to be working, I was instead writing short stories on legal pads at my desk and then mailing them (along with notes about how much I missed her) to my girlfriend, who was starting veterinary school downstate.

I also said how impossible a career as a writer seemed, and that after two or three years of school I’d be right back where I started, needing some kind of path toward a job with career potential. Shouldn’t I just give in to the inevitable and go to law school?

She gave me the best advice I’ve ever received, and advice I’ve never forgotten, even if I haven’t always followed it.

Run towards, young man, not from.

This advice was rooted in her family story. Her father had chosen Chicago because he knew of an apprentice program his GI Bill funds would cover that had a better-than-living wage at the end of it. Rather than simply running from his home, he ran toward opportunity, and it paid off as much as possible for his children and then his children’s children.

Grad school in creative writing it was. For three years, I didn’t worry about what was next, because I was doing precisely what I most wanted to be doing, deeply connected to the work on a daily basis.

Upon finishing grad school, the next thing I ran toward was building a life with the young woman to whom I’d been sending my short stories. That meant getting a good-enough-paying job to live independently and put money aside. The specifics of the work were not important, but I was fortunate to fall into a job as a market researcher for which I was well suited.

Our next phase was to run toward something my now-wife wanted to do -- get more training to become a veterinary specialist -- which brought me back into the classroom and set me on a trajectory as a contingent college instructor.[5]

I’ve reached quite a few dead ends on my path, and inevitably, my best move in each case was to stick it out at that terminus long enough to find something specific to run toward.

Sometimes the thing I started running toward had only a short time horizon, six months maybe, but I’ve found the act of starting that journey often brought forth more possibilities.

I left teaching full-time five and a half years ago and still don’t have a specific new career beyond being a guy who writes and does a lot of other stuff related to writing, but it’s working out pretty well. There’s some anxiety associated with not having an employer and a steady paycheck attached to a year-end W-2, but the psychological benefits of having something to run toward are considerable.

Run toward, not from, is essentially advice to engage with your agency, to move in the direction of freedom as best you’re able. I can’t say it’s 100 percent guaranteed, but as a place to start, it ain’t bad.

[1] Old-school fans of the show will remember it as the San Francisco cast, the one with Puck and AIDS activist Pedro Zamora.

[2] I made considerably more in that job in 1992 than any full-time teaching position I ever held, not even adjusting for inflation.

[3] I did make it past some kind of initial cut, having filled out a 20-plus-page questionnaire and then being invited to send in a tape of myself doing whatever it is I did. Having woken up to the fact that it was nonsense by this time, I never took that next step.

[4] The starting salaries for new associates when I worked there in the early ’90s were around $80,000 a year. They’re double that now.

[5] She did her internship year at our undergraduate alma mater, the University of Illinois. I applied for jobs as a lecturer and as a night security guard. The security guard would’ve paid slightly more, but the lecturer job was the right call.

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