This site has limited support for your browser. We recommend switching to Edge, Chrome, Safari, or Firefox.

Side Hustle Diaries: I'm A Freelance Writer With Imposter Syndrome

imposter syndrome

When people ask, “What do you do professionally?” I usually feel like an imposter in my response, “I’m a freelance writer.” I wonder if I’ll always feel the need to use air quotes around the word, “writer”. Maybe until the day I’ve sold X number of books or get published in some reputable magazine or finally achieve whatever goal it is I’ve created that will deem me worthy of this title.

Anyone that’s worked freelance can understand the anxiety that comes with it. When will I land my next project? How much should I charge? How do I manage my time? Can I afford health insurance? How do I file my taxes? To be honest, it can be tempting for me to want to take a secure job with benefits and a bi-weekly paycheck that I secretly hate. Writing’s never been my “main hustle”, I’ve always kept a full-time job that pays the bills and avoids any concern from family during the holidays about what I’m doing with my life. So, like every twenty-something year old girl living in New York City my writing started as a blog called, MeddyMade, which was more or less a platform to process my exciting new life in the city and the sabbatical I’d taken the year prior living in Hawaii and Australia working as a housekeeper, nanny, bartender, coffee shop toaster girl (as I said, I had a lot to process).

Writing wasn’t a profession I believed could be my full-time job. I had a love-hate relationship with my writing. When I was in the zone I loved it, and when I wasn’t I’d go dark, claim I was uninspired, and never write a word for years. It wasn’t until I became a copywriter at Ralph Lauren that I thought writing full time might be a possibility. The position didn’t prove to be as glamorous as I’d anticipated. Most days I was sitting in a room transcending ill-fitted, jersey-knit, mom tops into, “Cascading ruffles with a V-neckline add a touch of drama, making this decadent wrap the perfect after-dark option.” (insert vomit emoji). In short, corporate fashion did not fulfill my creative needs so, I found a blog in my neighborhood and proposed writing a dating column about pick-up lines and my failed romantic escapades.

Life took an unexpected turn when I moved to Los Angeles and was hired as a researcher on a show for The History Channel about UFOs called, “Hangar 1”. Due to some staffing issues, I got to take a stab at writing a couple of scripts, one being about underwater UFOs and the other, people being chased by said UFOs. Unfortunately, the show did not get a third season so I took a job I found on Craigslist seeking fashion copywriters. It was the classic start-up, I wore “many hats”. The most interesting being when my boss, a former celebrity stylist, asked me to pull outfits for Paris Hilton and deliver the $20K worth of clothing to her home in Beverly Hills that had a pink Bentley in the driveway. Months later a friend reached out and offered me a freelance job I couldn’t refuse back in NYC at a reputable fashion brand. I was making the most money I’d ever made but I felt as though I were in boot camp, working 18 hour days, learning to anticipate outlandish requests like where to buy the best matcha cake in Manhattan or standing in a line five blocks long to buy a dozen cronuts for an office birthday party. I was on track to make a pretty decent living but I couldn’t get over the fact that I was basically the fucking cake girl with a fancy title. What was this job preparing me for? I thought I had a lot more to offer than my position would ever allow and it became clear I had to move on.

I won’t bore you with my entire resume but as you can see I have changed jobs a lot. Looking back, I can see that my fear of immersing myself in writing prevented me from deciding whether I was even any good at it, or if I actually hated or if I just wasted all this time and now I’m old, and ugly and obviously useless (jk). I spent so much time taking EVERY opportunity out of fear I’d miss THE opportunity. You know, the one that magically launches me on my path to my future dream job, husband, and then children and ultimately a peaceful death preferably in my sleep in a place that my husband won’t be the first to find me because I once heard that when you die you apparently shit yourself and I really wouldn’t want that to be my last impression on the love of my life… I digress. Honestly, the only difference between me and freelance writers who don’t use air quotes was pretty simple, they were actually doing it. There’s some quote about inspiration being for amateurs and I couldn’t agree more, because anything worth going after takes discipline and practice. Call it cliché but knowing myself and what I’m capable of has taken me farther than any skill set, degree or financial advice ever will.

If I had to boil down the lessons I’ve learned up to this point there would be three. First, when I entered the workforce I didn’t know my ass from my elbow and how could I? I was 22 years old, from Maine, with a History degree and no real job experience trying to get into fashion, a field I knew little to nothing about. So, early on I learned that my network was my currency and if someone extended themselves or a contact of theirs I made it my mission for that person to walk away from meeting me thinking, “Wow, that girls got something”, my point is, you only get one first impression and you never know where it can lead. Second, difficult personalities are inevitable, I spent so much time wondering why someone didn’t like me and it got me nowhere. Third, have a sense of urgency, I’ve got a real tendency to overthink things and it gets in my way A LOT. Make a decision and take action, mistakes are necessary.

So where am I now? Well, I wish I could say that I now confidently consider myself a writer without any hesitation and that I live each day by the lessons listed above, but the truth is I’m still figuring it out. I still wonder why certain people don’t like me, I still stay in some nights eating ice cream and watching Netflix when I should be going to a networking event and I still overthink a lot of things. So, I can sit here and tell you to always remember to take 20% out of your paycheck for tax purposes, or the 10 best ways to avoid procrastination or how not working in your pajamas provides optimal productivity, but I’m not going to because none of that really matters and you won’t get it right the first or second or maybe even third time. My only words of wisdom are that you already have all those answers and I have to imagine you’re probably not reading this because you think I do, you’re probably reading this because you’re waiting for something or someone to give you the permission to say fuck it because only you can make that choice. So, in the famous words of NIKE, just do it.