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.


A few years ago, long after I’d moved out on my own — to the trendy Park Slope area of Brooklyn, where life was beautiful but expensive — I had a freak medical emergency. A vein burst in my abdominal area and I had nearly bled out before emergency exploratory surgery discovered the problem. I was unconscious for days, in the ICU for more than a week, and relegated to my parents’ home for six months as I recovered.

In the pre-Obamacare era, I did have insurance (the most basic kind, with a high deductible) through a freelancer’s organization. My hospital stays and surgeries straddled the end and beginning of two calendar years. Between that and related expenses, I found myself tens of thousands of dollars in debt with my savings wiped out completely. There were months where I couldn’t work, attend events, or travel.

I knew I was fortunate even to be alive, but I found myself far more concerned with making money to pay than I was with getting better. Covering my expenses occupied all my thoughts. At one point, I even hosted a Twitter party from the ICU — while getting blood transfusions — just to get any income I could.

More than two years have gone by, and I’m in good health again, but I no longer can be flippant about income. It’s not simply enough for me to “get by” anymore as long as I’m having fun. I now go to few daytime events and minimal trips — and any that I do attend have to be directly related to projects and assignments.

I treat my work now as I’d treat a traditional desk job. Much as if I was my own boss, I spend all day every day at my desk, pitching and writing. I know that the best way for me to be healthy and happy is to be diligent, to create the most content I can, for the steadiest of income.

I still love my work. I love that I can share my passions with the world and make a living at it. I’m still living my dream — but I’m no longer living in a dream world.

Aly Walansky is a freelance lifestyle writer based in New York City. Visit her on Twitter at @AlyWalansky.

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