Career Talk: The Truth Behind How I Became a Professional Writer

I received my undergrad degree the summer of 2008. By October, the Great Recession hit hard.

Rather than sit around waiting for a job to find me, I enrolled in graduate school, foolishly believing that with a Master’s degree (in an academic subject, no less), I would walk into a fantastic career job when I was ready.

Nearly a decade later, I can tell you—I wasn’t just a little mistaken; I was spectacularly wrong.

My struggle was real—and if you’re launching a career in the Art Department/Creative Services/Public Relations/Communications—yours inevitably will be, too.

Here’s the epic battle I faced to carve out a career as a professional writer and some of the big lessons I’ve learned along the way:

But First, the Waiting Room

The graduate student. Excited, fresh-faced, hopeful.

By the summer of 2010, I had finished all my grad classes, completed three internships (two unpaid, one paid) for major non-profits, and applied to nearly every company in the Bay Area. I’d reached the point where I was so desperate to find a paid writing gig I interviewed for the very same auto insurance adjuster position I’d held before I went graduate school.

It may seem like a strange fit, but insurance adjusters do a lot of technical writing. So, it isn’t as odd as it may first appear for a writer to end up in the insurance industry. Anyhow, it didn’t matter if my background fits one way or the other; I was turned down for that role, too.

When I asked for feedback—since this was a role I’d held (successfully) before I even went to grad school—the male interviewer explained to me, bluntly, he didn’t see the value in my advanced degree.

His reasoning was my additional education unbalanced my resume and revealed my apparent “dissatisfaction” with an insurance career. I didn’t grasp it at the time, but his reaction to my education should have been a red flag. In the years since that conversation, I’ve faced many men (including my step-father) who couldn’t understand why I bothered with an advanced education.

And they say we’ve broken through the glass ceiling (smh).

After that meeting, as I walked back to my car dejected and bereft, I realized my accomplishments had worked against me and not for me. For whatever reason, the fact I’d sought more education and experience in other industries, made me undesirable.

At that point, I hadn’t even gotten into the creative world yet; things were looking grim.

Here I am, on the last day of my third internship, trying to play coy but really scared shitless of the future.

I Pounded on that Damn Door till It Opened

By autumn, I had to call time-out on my Bay Area career search. It just wasn’t happening. With bills mounting, and student debt looming on the horizon, I still had my thesis to write if I wanted that graduate degree.

So, I packed up and moved back to my mom’s guest room in San Diego.

At this point in my millennial adulthood, I’d moved back and forth from my mom’s house so frequently, she’d taken to calling me her “boomerang child.” She also started telling me, in all seriousness, I didn’t need to be a bird that soared; I could be a chicken who ran really fast.

My mom’s funny, but she was right. I apparently wasn’t going to achieve that high-flying (pun intended) career job I’d always envisioned. It was time to start looking for things a little closer to the ground.

But even stuck in mom’s “Bed & Breakfast” room (again, my mom’s funny, she loves themed rooms) slaving away on my thesis, I didn’t give up. I kept knocking—and then pounding—on the door, and one day, I shit you not, it suddenly opened.

No seriously, here’s mom’s “B&B” room where I wrote my thesis and languished away waiting for my big break.

They Kept the Chain on the Door

Of course, when the “big break” happened, it wasn’t the way I’d envisioned it. Nowadays, I joke the door opened, but they kept the chain on it.

In other words, I got offered a job, in a creative field, at a prestigious research institute…but it was a temp role. The pay was less than what I had made in a paid internship role, and I wouldn’t get to do any writing (at least for the first two years.)

The straight truth: the job was the administrative assistant to the Chief Communications Officer.

The job entailed:

  • Get her Chai tea latte (large, Chai in hot water, 1 Splenda) nearly every morning
  • Guard her preferred parking space (so she didn’t have to walk from the back lot, and it would look like she came in earlier than she did)
  • Book her hotel rooms for weekend getaways with her husband
  • Make the labels for her files
  • Make photocopies of whatever bits of paper she’d leave on my seat (and never in my inbox)
  • Mail her correspondence
  • Reconcile her business credit card receipts (those little bits of paper actually mattered)
  • Order her lunch (and sometimes pick it up, too)
  • Clean up after her lunch meetings
  • Manage her calendar
  • Screen her calls/take messages/email to let her know if her boss (or other VIP individuals) had stopped by looking for her
  • etc., etc.

While these are perfectly acceptable career responsibilities, they were NOT what I had envisioned for my big career break. Plus, after interning three times in a row, it felt like I went back to square one.

In all truth, while I desperately needed the job experience, it was demoralizing for a woman with grandiose dreams for the future. All I wanted to do was to write anything—press releases, donor profiles, hell, parking instructions—but for the first two years, they just wouldn’t let me do that.

Today, I understand why.

Yes, I had been to college/graduate school; and yes, I had interned three times in progressive writing roles, but I was still a complete novice. I didn’t know what I didn’t know.

I look back, and I’m so embarrassed by myself and the foolish mistakes I made. I was angsty, frustrated, perpetually unsatisfied, and I showed it—to everyone. In those days, I lived up to many of the worst millennial stereotypes.

The biggest regret I have of all? I failed to see I created the unhappiness and anxiousness I felt.

Life isn’t always glamorous when you’re the coordinator.

The job wasn’t sold to me as a writing role; it had always been what it was. I just projected my career expectations onto it and expected everyone around me to translate the potential they knew I had into a practical skill—and that was my mistake.

If you’re just starting out and struggling in an assistant role (or trying your best to avoid one), try to see the job differently (despite how demoralized you feel) because there’s remarkable value in being the assistant.

I learned more practical knowledge in my three years as a coordinator than I ever did in graduate school. Why? Because in that role I received real-life examples of how to navigate (right or wrong) the actual challenges I would face later in my career.

When you’re the assistant, you’re privileged to witness an unobstructed view of someone else’s driving skills. If they’re talented, you’ll learn a hell of a lot from watching them. If they’re not, you’ll learn what not to do and why.

Despite my angst, the job wasn’t all bad—and my boss was a powerful role model for me in my career.

Yes, she did make me get her tea, and yes, I did have to hold a parking space for her, but she gave me my first real break, and I will always appreciate her for that. Was she kind to me? No, kind isn’t the word I’d use, but she taught me a lot—good and bad—and helped toughen up my skin by knocking me down a few times. Today, we’re friends, and she is one of my most vocal advocates.

So, I’ll leave you with a piece of sage advice she gave to me in the midst of ripping me a new asshole for a stupid mistake I made:

As I protested my innocence, crying out at the unfairness of the situation and her treatment of me, she stopped me mid-sentence, looked me straight in the eye, and said, “I don’t care. And I know that isn’t fair. But a fair is where you go on Sunday afternoon. It isn’t how you get to live your life. Figure that out, and you’ll make it a lot farther in your career.”

It was harsh, but—damn it—she was right.

When you shut up, stop protesting, and accept that life isn’t always going to be fair, it’s easier for the bruises and scrapes of your mistakes to become lessons—important ones that help to shape and grow you.

Admittedly, it took a few more missteps before I really understood her point: stop expecting the world to treat you fairly, stop looking for others to care the world isn’t treating you fairly, and stop hoping to find a sisterhood in the workplace that doesn’t exist.

Which leads to my next point…

Check back next week.

 In Career Talk Part II, I’ll cover:

  • Women Can Be More Challenging than Men
  • Mentorship Matters. Find One
  • Men (and the Ever-present Boy’s Club)

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