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Is freelancing only for trust fund babies?

Posted on Thu, Nov 16 2017 9:00 am by Kate Leibfried


The question was jarring. I found myself at a networking event for writers and wannabe writers, camped out at a table among strangers, when the woman next to me asked me about my career.

“I write professionally,” I told her. “I’m a freelancer.”

She gave a sniff. “What, are you a trust fund baby or something?”

Like I said, jarring.

My hackles rose; my fists clenched in defensive balls. “Not at all,” I responded. “I had to work hard to do this full-time. It didn’t just fall into my lap.”

The woman nodded, but her slight eye-roll betrayed her doubt.

The conversation moved on, but my brain remained stuck, rutted into the wheel tracks of her words. A “trust fund baby”? Why on earth would she think that?

The question bothered me so much that I spent most of the next morning brooding about it, dreaming up responses I could say to her as soon as I had access to a time machine. I pictured a soapbox speech about how I achieved my dreams through hard work and elbow grease, and she could too, damn it! Anyone could...right?

Something scritch-scratched at the walls of my indignation.

Could anyone pick up freelance writing?

I first dove into freelancing because I was desperate for a change. My feet were stuck in heavy tar, created by a soul-sucking job and an unhealthy relationship, and I needed to either get the hell out or surrender to the black goo. I chose to get out.

In a dramatic month, I quit my job, walked away from my partner, and started sleeping on my brother’s couch. I picked up a part-time job slinging pancakes and coffee at a breakfast joint and began hunting for writing clients. My days started at 4:30 a. m. and often didn’t end until past midnight (mostly due to my brother’s roommate and his late-night recording sessions, featuring homespun rap backed with the thrum of heavy bass).

I had to do a lot of pride-swallowing during that time, especially when old college acquaintances found their way into the breakfast establishment where I worked and inevitably sat in my section.

I’d walk like a wooden soldier to their table, coffee pot clutched with white knuckles. Act natural, I’d think. There’s no reason to be ashamed.

My cheeks would burn. I’d wait for the moment of recognition, when my ex-classmate would look up from their conversation and acknowledge the person in the red apron, hovering awkwardly at their elbow.

“Oh, Kate! Hi! Umm…you look well.”

“I do this on the side,” I’d blurt. “I’m writing now. Building up my client list.”

They’d nod, pretend to believe me.

“That’s great. Really great.”

Could they smell my desperation? Did they know I had amassed a collection of seven different jobs (only three of which involved writing), just so I could move out of my brother’s place and into a shared duplex? Did they realize I rotated between two pairs of black pants at the restaurant, because I couldn’t afford any more?

It’s easy to slip into self-pity mode when I think back on the hardships and chaos of that time, but to pity myself would mean to deny the whole truth. The truth is, I am privileged.

The lady at the networking event was right.

If I hadn’t had a supportive, generous family member in town, I would have never quit my job.

If I hadn’t been raised with education at the center of my life, I might not have attended or graduated from college.

If a couple of my friends hadn’t connected me with two business women seeking a freelance writer, I might not have landed my first two gigs as easily as I did.

If I hadn’t met and moved in with a supportive partner who encouraged me to write full-time, I couldn’t have quit my serving job after only two years of waiting tables.

Privilege is a skittish animal. Whenever I try to confront it, it ducks out of sight and plunges into its den. It’s easier to leave it alone than to coax it to the surface. For me, it took the flippant words of a random woman to grab the animal by the throat and wave it in front of my rose-tinted eyes.

With the animal exposed, I’ve realized that my privilege doesn’t cheapen where I am today. If anything, it helps me appreciate the support, connections, and experiences that have shaped my life’s path. My personal journey hasn’t been a solo project. It’s an amalgamation of encouragement, generosity, and bleary-eyed nights of attempting to write through the BOM-BOM-zippee-Waaaa of midnight rap sessions.

My trust fund—the wealth of resources and support I’ve been given—exists. But it doesn’t diminish the hard work, expended emotional energy, and personal sacrifices I’ve made to finally reach the point where I can walk into a networking event, head held high, and say, "Hi, I'm Kate. I'm a freelance writer."

Kate Leibfried is a freelance writer, book-writing coach, and founder of Click Clack Writing, LLC. She has written for companies as diverse as the Ordway Center for Performing Arts, Sun Country Airlines, and 3M. In her alternative life, she writes fiction under the pen name Kate Bitters and has written three novels, a children's book, and has had her short stories published by MPR, Horror Tree, and Short Story MeOne of her proudest/nerdiest moments occurred in 2015 when Neil Gaiman read her prize-winning short story on the Fitzgerald Theater stage.