Jumping off the high dive: Freelancing the first year

Elizabeth Donald
Oct 18 · 5 min read

A cute article from the Freelancers Union caught my attention this morning: This freelancer threw herself a company party and you should, too.

It’s a little too cute — I can’t quite get behind giving myself a speech or a team-bonding activity with just me. But I can definitely get behind the happy hour.

In all seriousness, somehow the one-year anniversary of establishing Donald Media as my freelance company kind of slipped my attention. July 27, 2018 was the day I packed up my desk at the newspaper where I had worked for 18 of my 21 years as a journalist, took a couple of pictures of the silent newsroom and left my key card under the door of the human resources office. I was working the night shift that month, so there wasn’t a cheering crowd when I walked out that night — we’d had our cupcake celebration a day before, but three of my colleagues had to miss it to cover a Trump rally.

The door closed behind me as I left, and I heard it lock behind me.

I’d been planning for a year, and launched my freelance site more than a month beforehand when I announced my impending departure and launched a Patreon, which was my first freelance endeavor.

It’s funny — a lot of the things they tell you to do when you go freelance were impossible for me. I could not begin freelancing on the side to build up a client base while I was still at the newspaper, because it would have been a violation of my terms of employment to write for competitor publications while I was on staff. I had an established fan base for my fiction work, which was not considered a conflict, but I had to wait until I was actually gone before I could query potential clients.

It’s kind of like jumping off the high dive and waiting until you’re in midair before you see if there’s water in the pool.

I didn’t go splat. I didn’t immediately start making six figures, either. I started in what I knew — local news — and that continues to be a major income stream for me. I branched out into magazines and find that they really suit me well. I used to joke at the newspaper that I was built for magazines, because I was famous for writing too long. It turns out that wasn’t a joke.

I did stumble quite a bit that first six months. I had a plan, of course: I had applied for and received a teaching assistantship to earn a masters in media studies at the local university, and I would launch my freelance business at the same time. Then I realized why the experienced freelancers shook their heads sadly when I shared my exciting plans. They knew that “full time” for a freelancer is a hell of a lot more than 40 hours a week at a desk.

That first semester nearly killed me, and I was only taking two classes and teaching one. The work load of balancing grad school and launching a freelance career was only part of it: academia required an entirely different mindset and manner of writing and research than journalism, and it was a difficult adjustment.

This semester is actually easier, with three classes as student and one as teacher, because two of them are independent studies. And by “easier” I mean that I’m not staring at myself in the mirror and chanting “you have not made the biggest mistake of your life” and “yes, you are smart enough for this.”

It did get disheartening sometimes, especially in those early months when I only had one or two clients and my Contently portfolio was thin. There’s also the matter of my family: I have a husband and son who are also in college as undergrads, and sometimes we are up to our eyeballs all at the same time. I have an obligation to my family for my time, support, food and finance, and that requires diligent effort.

Then my work took another side turn when I took a class in creative nonfiction. It was just supposed to be an elective to supplement media studies, but it turns out I absolutely love it. I was always writing creative nonfiction in the form of personal essays and the occasional rant, but I didn’t know there was a form to it, or that I’d be really good at it. Or that people would pay me for it.

In many ways, the practice I got in that class has reformed my image of what Donald Media can be — and really, Donald Media is the term for all my freelance work under one umbrella:

  • Local news reporting (including the student newspaper)
  • Magazine journalism.
  • Volunteer work with the Society of Professional Journalists and public speaking advocacy for the profession.
  • Photography, both news and artistic.
  • Creative nonfiction/essays on Patreon and Medium.
  • The blog series: CultureGeek, Patreon, Literary Underworld, and here.
  • Editing and writing coaching in fiction and nonfiction.

All of that is partnered with my fiction work (albeit only short stories until I finish the bloody masters), my teaching, and of course school. Assuming I pass everything this semester and next, finish and defend Ye Olde Thesis, and I will have the masters, which makes me eligible to keep teaching and warping young minds into this profession I love.

It looks like a lot. It IS a lot. I’m working harder than I’ve ever worked in my life, and with that I include the 65-hour weeks constantly on call at my first full-time reporting job with a baby at home.

It’s stressful and difficult and the money is what it is and sometimes I have to chase it. But I have the great privilege of doing the work I love and being my own master, and I wouldn’t trade that for anything.

So, happy year one to the troop(s), congrats on all we’ve done, and here’s to that happy hour.

Elizabeth Donald

Written by

Journalist for more than 20 years, president of St. Louis SPJ, masters candidate/teaching assistant, freelance writer, editor, photographer, and fiction author.

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