When Working for Myself Lost Its Glamour

working for myself

I always knew I’d become a writer.

My eyes were somewhat starry. I thought I’d get a journalism degree, graduate, and immediately become Carrie Bradshaw. The reality was that right out of college, I landed a job copy editing at an educational publishing house. It wasn’t nearly the lyrical prose I had imagined.

I worked in that field for a few years, getting used to the daily monotony, my dream feeling less and less like my own. Then, one day, half my department was laid off due to budget cuts. (Turns out children don’t really like educational nonfiction.)

Having no idea what to do with myself, I took random temp proofreading jobs. But I was bored. I wanted more, and I knew I needed more.

I was also lucky. I was in my early twenties, and like many children of New York, still lived with my parents. I was desperate to move out and be on my own, but this gave me the padding I needed to throw caution to the wind and finally give a career in writing a try.

It was a slow start. A decade ago, the digital world wasn’t what it is now. It was an era of sending an SASE (that’s self-addressed stamped envelopes, young ones) every time you wanted to pitch a publication. Slowly, I got bites. At the start, every byline felt like a million dollars, like tangible proof I was finally going to be making a living. The more I worked at it, the more steady work appeared.

But that wasn’t the only thing that made me feel amazing. I loved the sexiness — the “Carrie Bradshaw” of it all. I grew up an introvert with a small circle of friends in a remote area of Brooklyn. Then all of a sudden, I was going out to nightly launches and premieres. The early years of building a freelance career are very much about relationship building, and I gave just as much of my time and energy to lunches and cocktail parties, trips and receptions, as sitting at my desk pitching and writing.

I was content to live from project to project, thinking that having enough work to pay my immediate bills — and a whole lot of fun — was living my best life.

But it was a shortsighted fantasy.

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