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Advice / Career Paths / Career Change

The Road Less Traveled: Navigating a Non-Traditional Career Path

You finally did it: You found your passion. You quit your stable job or declared an artsy major and chose to climb the untamed trail of Robert Frost instead of driving the corporate freeway to success.

Now what?

Unlike the attorneys and accountants you know, your trajectory isn’t neatly outlined in an employee handbook. Instead, you’ll have to create your own roadmap. You’ll draw on all of your resources, employ a bit of trial and error, doubt yourself (then learn to trust yourself), and do it all while the people around you tell you, “you can’t.”

If you’re taking a non-traditional career path, you’ll probably hear from friends, family, colleagues, and maybe even your own head that you’ll never make money or find a job. But, take it from me: It’s all worth it to make your crazy dream a reality. I know, because I, too, chose to climb this bruising yet beautiful trail.

From Finance to Freelance

Upon leaving college, I followed the path of least resistance to Finance. It was a good job, a stable job. It made my mother, the biggest proponent of the corporate highway, proud.

I spent seven years battling the boys’ club where superiors blew off harassment with a wink and nudge and my only function was to charm our clients, then make them richer. At the end of the day, I came home depleted, depressed, and uninspired.

So I started a blog.

I was desperate to find my passion, so I took one-week challenges from my friends and family and spent my days in some of the strangest and most uncomfortable situations I could dream up. I have a severe case of stage fright and yet performed five minutes of stand-up comedy and sang karaoke. I have issues with body image (including a brief tour of duty as an anorexic) and I posed nude for a figure drawing class. I’m not an affectionate person, and I gave away free hugs in San Francisco and Dublin, Ireland.

And in the process of experiencing, observing, recording, and writing, I found my passion: writing. It was all I wanted to do.

I tried to cultivate this skill while maintaining my job, but the trajectory of my career was coming to a head, and I had to make a decision. Was I going to stay on my current path and invest more time and energy into a profession that left me empty, or was I going to pursue a dream that made me whole?

So, six months after starting the blog, I quit my finance job, and announced that I was going to become “a writer,” even though I had no idea what that meant. I wrote for practically free, and I moved home to save money and cried more than once on my parents couch.

But you know what? It all worked out. Two years later, I’m a successful freelance writer who lives in her own apartment and can claim The Atlantic on her resume. I’m also turning my blog into a book.

Negative Nancy and Her Two Sisters

That said, it wasn’t exactly easy. I quickly learned that, when choosing to bushwhack your way to a more fulfilling life, you’ll likely encounter boulders and fallen trees. I fought bitterly with my mother, who favors obligations and paid bills over creative pursuits, and I met with writers who told me the trail was fraught with potholes, ditches, and dead-ends. I was constantly stressed about my non-income, and I dealt with crippling self-doubt.

But, in the process of following my dreams, I learned to climb over those roadblocks. Now, looking back, here’s advice I’d give to anyone considering a similar path.

Roadblock 1: Detractors

You will always have people who tell you, “You can,” and people who tell you, “You can’t.” My advice: Keep the “cans” on speed dial. In the beginning, my self-confidence was fragile, and it was important to surround myself with the people who supported my decision and keep my contact with those who didn’t to a minimum.

But, I also learned to stop arguing with the “can’ts.” When I was first confronted by people who had concerns about my path, my knee-jerk reaction was to stomp my foot and throw a tantrum. Obviously, this got me nowhere. And eventually, I realized that my detractors had some valid points, so I shut my mouth and started listening. I picked up the advice I needed, left the rest on the table, and moved on.

It also helped to develop an elevator pitch. Many people wanted to know, “How are you going to be successful?” And once I had a five-minute spiel that provided the vague idea of a plan, my conversations got a lot easier.

Roadblock 2: Financial Stresses

Unfortunately, most grocery stores won’t take IOU’s, but it is possible to survive on a low-paying (or no-paying) salary if you’re willing to make sacrifices.

For starters, I worked part-time. For the first four months of my new endeavor, I worked three days a week at my former firm and dedicated the rest of my time to freelancing. This gave me a little guaranteed income to smooth the transition from stable job to not-so-stable career.

I also moved home. Yes, I left a vibrant city for the monotony of suburbia and gave up a deep support network for barbed questions at my mother’s dinner table. It was rough, but I was able to focus on my writing as opposed to worrying about rent.

This won’t work for everyone, but if you’re really considering taking a major pay cut, you’ll need to think about the changes and the sacrifices you can—and are willing to—make in order to make your dream happen.

Roadblock 3: Crippling Self-Doubt

For some, the biggest hurdle you’ll have to overcome is your own head—especially at the beginning, when your successes are few and far between. So, it’s crucial to stay in touch with the inner voice that ignited your passion in the first place. For example, whenever I struggle with the choices I’ve made, I go back and re-read a favorite piece I’ve written. It’s an ego-stroke that reminds me, “Oh yeah, I’m good at this. I’ll be fine.”

I also learned to get comfortable with the phrase, “I don’t know.” You don’t have to have everything figured out—and you definitely don’t have to have it figured out today. Over the last two years, I’ve had a lot of “plans.” I’ve thought that I had all the answers, then realized I had none of the answers, then thought I had them all again. After the third iteration of this cycle, I realized that I might not ever know how it’s all going to “work out.” But, you know what? I’m OK with that.

The unruly trail of Robert Frost is a climb that often leaves us bruised, cut, and tired in spirit. But we choose it because something within us tells us we must. So, keep climbing. Though your map may be flawed and your methods unconventional, when you get to the top of our mountain, you’ll be thrilled—and grateful, too, for the journey.

Photo courtesy of Jack Batchelor.