From Office Manager to Freelance Writer: How I Built My Career

When I was 26, I moved to New York City to be a writer. It was my dream, and I was going to make it happen.

But, of course, that’s easier said than done. So when I got to the city, I landed a job as an office manager. I worked for a couple different companies over a few years, always writing on the side—but I was terrified to take any major steps toward my dream.

Why? Well, like many of us, it was the fear of rejection. I’ve never been good at rejection, but I knew that it was a big part of being a writer. If you think being dumped on your birthday when you have mono is bad, try getting an email that pretty much tells you to go sell crazy elsewhere—they’re not interested. Also try getting that rejection email almost every day for months and months.

But I finally manned up. I had moved with a purpose, and it was time to fulfill that purpose. Plus, there are only so many fake accents in which you can answer the phone when you’re an office manager before you truly start to lose your mind.

Of course, I wasn’t exactly sure how I was going to pull it off. But I figured that the best place to start was from the bottom up. For anyone who’s ever wanted to be a writer—here’s what I did, what worked and what didn’t, and what I learned along the way.

Putting Myself Out There

My first step was to contact anyone I even slightly knew in the industry. Whether they were writers, editors, publishers, assistants—it didn’t matter. If I had met someone even once before, I emailed her asking if she knew of any places that were accepting pitches from freelancers. I also made a list of all the places I’d love to write, and started contacting editors and pitching stories.

And I did get a few leads through these efforts, but nothing really stuck.

So, I took the next step: networking. The fact of the matter is that no one in this industry will give you a chance unless you know someone else. I know, it’s always awkward at first to sit down with a stranger and pick her brain, but I forced myself to do it. I made myself contact bloggers and writers at women’s interest sites and either meet them for drinks or get their feedback via email. Even though some of these editors wouldn’t give my work the time of day, they were more than happy to talk about their own experiences. Everyone’s favorite subject is themselves.

And I can’t tell you how insanely valuable this was. I got tips on not only how to pitch, but how to angle those pitches so they were unique. I learned that writing was just one part of the ball game: Sure, I could craft witty sentences and paragraphs, but in order to actually get jobs doing so, I was going to need to learn how to speak editors’ language.

Name Dropping: Sometimes it’s Necessary

After doing some practice pitches with my writer friends, I started hitting up editors. Now, let me tell you: If you’re dealing with a publication or site that isn’t brand new, it’s hard to get an editor to pay attention to what you have to offer. Even if you’re the next J.D. Salinger, if they haven’t heard your name, there’s a good chance that you’ll either be ignored or directly sent to the spam or trash folder.

So as much as it pained me to do so, I started name-dropping. I even put names of people that editors and I had in common in the subject: “Hey there! Sally Sue sent me your way!” It’s not exactly the classiest of moves, but it does get an editor’s attention. I found that 9 times out of 10, I’d get a response.

Taking the Plunge

So, finally, I started getting jobs. I was in no position to quit my full-time job, of course—but once I had enough editors who were interested in my ideas, I started writing both at night and on the weekends. I wasn’t being paid much (online freelancing gigs can get you anything from $25 to $250, unless you’re famous), and it often meant staying in on a Thursday night to meet a 9 AM deadline, but it didn’t matter—I was doing what I loved. I debated trying to find a part-time job, so I could dedicate the other 50% of my workday to writing, but at the time it didn’t seem feasible. It was a good goal for down the road, but I figured that, if I was only doing a couple pieces a week, giving up my full-time job might come back to bite me in the ass.

Then, one night, at a party with some of my new writer friends, I was introduced to someone—and she actually recognized my name! Just earlier that week, she had read an article I had written for AOL. I couldn’t believe it. I felt like a rockstar (OK, in a very small way, but still), and it hit me that it was time to really do something about my writing career.

Not long after that fateful evening, I was laid off (it was 2008), and I figured it was a sign that I had to go for it. I knew I wasn’t going to be making the money I was before—in fact, I knew it was going to be a struggle financially—but I also knew that if I didn’t take the chance, I’d regret it forever.

No Pain, No Gain

That was almost four years ago, and today, as I sit here (in my underwear) at my desk in my bedroom, I am officially a full-time freelance writer. It wasn’t easy, and sometimes I feel like I wasted time, taking years to find the necessary confidence in my work to be a writer. But no matter how long it took, I’m here now and that’s all that really matters.

Oh, and the rejection stuff? Rejection from editors is a walk in the park compared to what commenters sometimes have to say about your work. While bloggers know that a lot of online commenters are just trolls looking to be cruel to someone they can’t see, it takes a lot of practice to either let it roll off your back or just learn to never read the comments—ever. I’ve realized that writing is like exposing a vein: You’re putting yourself out there to be ripped apart.

But I also had to ask myself which was worse: Sitting behind a desk at a company I loathed answering phones for nine hours a day, or being insulted by a bunch of commenters I’ll never meet? I’ll take the latter every time, yes, even when the comments cut deep enough to bring me to tears.

Here’s my advice to you: When it comes to following a dream outside of your day job, you have to be willing to take risks, open yourself up to new things, and even face fears like rejection and not being able to pay your bills. But in the end? You can do it. And, take it from me: You’ll be so happy you did.

Photo of woman writing courtesy of Shutterstock.

About the Author

Amanda Chatel is a freelance writer in New York City. She has written for AOL's Lemondrop and MyDaily, The Grindstone, New York Magazine, HowAboutWe and is a frequent contributor to The Gloss, YourTango, BlackBook, and the Huffington Post. She lives in the East Village with her dog, Hubbell, who is named after the Robert Redford character in The Way We Were, and not the telescope. People never catch the difference in spelling.