10 things I hated about me (the 1st time I freelanced)

A recession is not a bad time to start a business. I learned that the first crash. Ad agencies and architects especially got hit hard in late 2008, as if the economy lazily went gunning for whatever’s listed first in the yellow pages.

The world is tenuous. We learn that in waves of revelation. Especially lately. Some crashes are big and land hard, wiping out a lot of things that looked like they would last. Like, way back then, my boutique ad agency job as a junior copywriter.

In 2009, the freelance world appeared mirage-like before me. Agencies had scaled back, but Capitalism, being a cancer, guarantees that businesses are always in some stage of metastatic bloom. And they needed copy, stat. This future seemed tenuous too, but at least the instability would be dictated by me. I was making actual dollah bills that paid the bills. All with words. It felt like magic. It still does.

Unfortunately, I did not realize I was a certifiably terrible businessperson.

Until now. Call it hindsight. All the 20/20 lookbacks in 2020 (even though I’m myopic). It’s no wonder that flying by the seat of my pants eventually turned to running on fumes several years later. Take this list as 10 things not to do when starting a freelance business.

#1: I thought like a poor person. Because I always had been a poor person. I had no vision for myself that wasn’t a starving artist type. This scarcity mentality never really leaves you until you root it out completely. (Fist bump, therapy.) I had a monthly number in mind that would cover my meager bills, and I always reached (but never really exceeded) that number.

#2: Imposter syndrome. The first recession (am I really calling it that so early in the “second” recession’s gestation?), I was junior. Fresh meat. Seared for a few years on each side in ad agency hot spots. I didn’t exactly know what I was doing.

#3: I took on any project. I didn’t know what type of writing to focus on, so I did everything anyone asked of me at a low price. From writing a wine cookbook (even though wine and I have a vomitous relationship) to penning multi-page guidebooks for the AARP, I was a “yes” girl, in the vein of Peggy Olson in early Mad Men seasons.

#4: All my clients came by word of mouth. Don’t get me wrong, I love word of mouth. I was so proud of the fact that all of my clients came from word of mouth. Until I (much) later realized…I didn’t really try…did I?

#5: A side project took over my life. My artsy brainchild became a wunderkind. Thus Story Story Night, a monthly live storytelling show (eventually turned nonprofit), took over my life for six years. I kept up with it like a stage mom running after her child star. It was thrilling, ecstatic, and exhausting work. Largely unpaid. It was my main job and priority, really, with my freelance business (that actually paid my bills) becoming my side project.

#6: No real routine. My routine was…unhinged. Morning, noon, or night, I had no conscious idea what I’d be up to. But I knew one thing…I’d probably be running late.

#7: I worked all the time to little effect. Random AF is not a fabulous way to achieve a healthy work/life (or bank account) balance. I always had to be doing something but was simultaneously always distracting myself from all the somethings I had to do. I never got off the false productivity hamster wheel.

#8: No discernible business systems / strategies. I didn’t really have financial forecasts, revenue goals, and project management or accounting systems in place. April 15 gave me literal hives.

#9: I stayed at the same rate. Over seven years, I never raised my (already too low) rates or thought about building my business or client base strategically until it was too late.

#10: No coping skills, especially for the unrelenting stress of success. I saw the blaring light of the burnout trainwreck coming, so I developed clear boundaries and healthy coping strategies. PSYCH! I was a hot mess—constantly flooded with stress hormones. I spent all day putting out fires even as I started them. Then sobbed in overwhelm on the velvet gold couch.

The crash and the burn and the “better get a full-time job stat,” I now see, were inevitable. Especially since my one coping mechanism for overwhelm is the inglorious capacity to self-sabotage spectacularly.

I was the shittiest business person ever to business. As foretold by the back of my mind, I became the starvingest of artists, instead.

Burnout takes years and years (and therapy) to fully recover from. Especially if you want to use it to Phoenix yourself into the version of you that you know you could’ve been, if you only knew better (and actually…tried).

Next time, I’ll give you my Uno Reverse card tips for building a better freelance business.