Don’t Let Your Creativity Hold You Back from Writing for Money

My mind has held business and creativity in two separate compartments for as long as I can remember. My dad was a sales executive for a major pharmaceutical company. When I was seven or eight I accompanied him to work. I toted a neon pink briefcase, and penned in my journal about the shiny world clocks on display and the underground tunnel at Abbott’s corporate headquarters in Chicagoland.

He had a nice office with a huge dark desk and his own secretary. The building had a sterile smell, like new carpet. Aside from the occasional phone ringing or solitary knock on my dad’s office door, it was silent. There was an extreme reverence to everyone’s hushedness, and fascinating as it was, I didn’t believe this sort of work life would ever be “for me.” As I grew up, I believed that the best I could do for myself professionally would be to become an English teacher who writes novels on the side, so I went to college to learn exactly that.

Five turbulent years later, I was serving tables and putting the finishing touches on a novel that most certainly wasn’t The Great American One but I was absolutely certain would be groundbreaking once the right agent deemed it so. I am talking, of course, about the first novel I wrote as an adult, the meandering one I could have aptly named “Drunken Lesbians Fall in Love and Wonder About Life.”

My rejections were mostly photocopied form letters. Occasionally, a handwritten note would play accompaniment to the template, one insisting I “keep submitting,” another, “we hope you’ll find a fit for your unique brand of passion.” Whatever that meant.

What is Freelance Writing?

Freelance writing is the act of producing written content under contract for various clients, often simultaneously. The work is often location-independent, and freelance writers must pay both Federal and state taxes as sole proprietors.

Or, as a teenaged coworker at the restaurant where I worked naively (or ironically?) asked, “does that mean writing for free?”

At some point, I became curious about article and magazine writers, copywriters and technical writers, these people who seemed to make money writing. I picked up a book called “Six Figure Freelancing,” which was full of promises for someone with corporate experience, or a financial support system.

Or, at the very least, for people whose amygdalas were unfettered with troublesome quirks.

Still, this freelancing thing suddenly seemed so romantic and hopeful. If I did it, I knew I’d have to work hard, but deep down I knew I’d be breaking six figures within a year, just like the author of the book did. Actually, I would be making more, probably, and the author would just happen to attend one of the conferences at which I was the keynote speaker, and she would start a slow clap when I acknowledged that she was the very person who inspired me to quit my server job and chase my passion. We would meet for wine and cheese and toast our writerly lives.

Until I read that book, my plan had been to stay in the restaurant industry for financial security. I believed I could comfortably wait tables for the rest of my life as long as I got to write and do art in my free time.

But that Six Figures book had me all jacked up and plan-changey-feeling. Shortly after slapping the book shut with a decisive nod, I carried my notice up to my manager. I apologized for sending him mixed signals about my goals.

He was surprised, and I was, too, but this wasn’t the first time I had turned completely around to walk in a different direction. Being in my brain often feels like several different people trying to live out their vastly different goals at the same time. But as it turns out, going into business for yourself requires this particular type of madness.

Running a Writing Business

Freelancing is dangerous because you don’t get the guarantee of a paycheck, or benefits. You have to look out for yourself, and you have to be okay living on peanut butter and dreams for a little while.

But you know what they say about great risk.

I am looking back at my 23 year-old self from my current vantage point, seven years later, where through a tremendous amount of hard work I have reached a point where I now spend most of my time writing rather than searching for clients.

I’m still pretty terrible at personal money management, which often makes for tense times between paychecks. I have grown to understand major concepts in digital marketing, but my lack of a formal business education invites in a wicked case of impostor syndrome.

The beautiful thing about becoming “the businessperson” is that even though there are, and probably always will be, bigger and stronger and richer people doing better than you, freelancing really does mean more freedom. But by not signing your talent over to one sole company, as a salaried job would require, you become free to roam. Free to walk away from clients who treat you like a cog, or a slave, or something replaceable.

You have to be okay living on peanut butter and dreams for a little while. Click To Tweet

So you may not feel like a businessperson when you start writing for a living. This stuff may be confusing at times, both to your sense of artistic valor and your very brain as you discover the stunning complexity of spreadsheets, but think of everything you’re going to get out of this arrangement, and think of the solidarity you’re going to build with other freelance creatives who kicked the cubicle long ago and said, “You know what? Fuck this. My life is mine, and so is my work.”

And you know, you may wind up like me, unwittingly overjoyed to become reacquainted with your inner tycoon, lugging that neon pink briefcase like a boss.

Want more writing advice like this? Amanda tells it like it is in The New Freelance: A Book for Writers

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