From 2006 to 2016, I played the role of the diligent and dedicated desk jockey for a lot of companies. And by “a lot of companies”, I mean I pretty much set the standard for how job-hopping millennials should approach their careers. (You’re welcome, millennials.)

The thing is though, my gut was always telling me there was something wrong with these jobs, that this wasn’t the career path I wanted. My mind, however, tried to rationalize this practical approach:

“You’ve got to pay the bills.”

“Once you get past the learning curve, it’ll be fine.”

“This is what you majored in. Might as well put the investment to good use.”

“But this is what everyone else does. We can’t all be crazy for doing this, can we?”

“She’ll get fired. I mean, they have to fire her, right? Then everything will be okay.”

“Just make it to your two-year anniversary and then you can start looking for another job.”

“Their personal drama isn’t your problem. Ignore it and just focus on the music coming from your headphones.”

“I guess I’ve had worse jobs than this.”

As the years drew on, my body and mind both struggled with my choice of profession. Depression, anxiety, IBS, insomnia, stress, anger, binge-eating, denial… You’d have thought I was grappling with something like a serious illness of death, but it was just these stupid office jobs breaking me down, Monday through Friday, 40 to 60 hours a week. At the same time, I kept having these fantasies about being a famous writer with a totally blissful and easy-breezy life. While my post-desk jockey life hasn’t fully aligned with my fantasy just yet, I can honestly say there really is something to the whole “follow your dreams” thing.

I don’t know where you currently stand in your life. Maybe you’re struggling with your career path as I had. Maybe you’re unsure of a relationship you’re currently in. Or maybe you just don’t know whether you should eat that quart of ice cream tonight. Whatever it is you’re questioning, I hope my story helps.

The End of My Super Conventional Desk Jockey Career

There are a lot of words that could be used to describe me. Sarcastic. Annoying. Know-it-all. Loud. Crazy. Self-centered. But the one I think sums me up best is:

Unconventional

This is what the definition of “unconventional” should look like in the dictionary.

Although I’ve embraced my oddball nature over the years, there’s always been one part of my life where I tried to maintain some sort of conventionalism: my desk jockey career.

While I often struggle with the fact that I willingly spent a decade tied up in a career path that I had absolutely no interest in, I don’t know that I could’ve made a career in writing work, say, five or even ten years ago. It’s not that I didn’t have the experience or that I was somehow incapable of creating high-quality work then, it was more that the resources I use now to make all this work just weren’t readily available then.

I write a lot about technology these days:

What I always find interesting is that no matter what type of technology I write about, there is always this underlying idea that we need technology to streamline and improve our lives. As someone who recently quit her desk jockey career to pursue writing full-time, I can personally attest to this. Without the Internet, social media, digital marketing, or the multitude of cloud-based software I use on a regular basis, I wouldn’t have been able to make this work so easily.

Breaking the Cycle

When I found my last full-time job, I thought maybe it would be a good compromise for me: I would still have to slog through the typical desk jockey responsibilities, but it could be done remotely. That job turned out to be no different than the other toxic environments I’d worked in: it was extremely disorganized, full of personal dramas, and run in a very unethical manner. It didn’t take long for me to discover all this either, but I chose to stick with it for a few years because I was tired of balancing the stress of a full-time job with my part-time work job-hunting.

Then, about two years ago I decided I had had it. Enough was enough. My IBS was out of control. My doctors were shoving anxiety and depression meds at me left and right. And I couldn’t sleep. Rather than find some random job to replace the one I had and start up this unhealthy cycle all over again, I decided to give writing a serious go.

Time and time again people have always questioned my unconventional lifestyle. Why don’t you go back to school and get another degree? When will you stop going to the movies by yourself? Have you spoken to your family? Why do you love haunted houses? Why aren’t you married? When are you gonna pop babies out of your vagina? When will you stop moving/running away? Will you ever be normal?

To be honest, I’d normally say that I.D.G.A.F., but that continuous stream of commentary on my life’s choices did rub off a little bit when it came to work. I always dreamed of being a writer, but found myself too embarrassed to share that information with others. And as the writing job applications came back rejected or with no response at all, I wondered if I was mistaken, if maybe I just needed to stick it out as a desk jockey until I found a job where I’d be okay climbing the corporate ladder.

And then one day I saw a post on Facebook from an old coworker whose company was looking for freelance writers. I sent in my application as a sort of Hail Mary, and ended up getting the gig. It wasn’t the first time I had been hired to write for a company, but it was the first time I got paid for it. I can honestly say that my life changed the moment I started writing for them. I wasn’t making beaucoup bucks or anything, but it was the first time I realized I could really do this, I could make a career out of my writing.

And I was so fucking happy.

  • As I started to pick up more clients and build my business, I actually looked forward to the nights and weekends when I’d work as a writer.
  • I enjoyed every bit of my writing work, even when it meant hours of extensive research, calls with new clients, or other tasks that I would’ve dreaded in my day job.
  • I got so excited about finding more work that I built in time every day to casually peruse the web for more. I also set up job alerts and subscribed to freelance writing websites.
  • Charlie got more “mommy & me” time: longer walks, more exciting “adventures”, better belly rubs, daily nap times, and I even took over his grooming.
  • When I wasn’t writing, I tried to keep my focus on fun little trips. Going to see friends in Delaware, taking my boyfriend to New York City for the first time, seeing Niagara Falls, visiting the Rehoboth Beach boardwalk…

Killing My Career

By the time April of this year rolled around, my life outside of work had done a complete 180 from where it had been the previous year. As I sorted out all of the details and worked on relaunching my website around this new business venture, I grew anxious to be done with my job once and for all. I knew it was time to cut the cord.

In May, after I secured two more new clients, I had the talk with my boss. It didn’t go well (as I had expected) and the last two weeks ended up being extremely stressful and awkward. To be honest, I’m really thankful that’s the way my desk jockey career ended. It just served as another reminder of why that sort of work and environment was all wrong for me.

Living the Dream

In June, I officially became a full-time freelance writer and I officially started taking better care of myself again. I now:

  • Work out regularly.
  • Talk to the neighbors around the apartment complex more.
  • Nag my boyfriend less (I think).
  • Take vitamins daily.
  • Make time to go to the doctor when there’s something wrong.
  • Sleep through the night.
  • Try new foods, regardless of how long they’ll take me to prepare.
  • Take a couple hours every night to veg out with TV or a movie so I can properly unwind before bed.
  • Subscribe to a variety of magazines so I can read more about my profession, the industries I write for, as well as the world around me.

In general, I just feel better.

I realize there’s a lot more work I have to manage myself as a freelancer, but I’m willing to make that tradeoff. I can secure all the required insurances, manage my own website, build my client base, tend to my complicated finances, etc. because it is worth it. Like I said before, there really is something to following your dreams. I know it’s still pretty early on, but I have a good feeling about all this.