Freelancing: The Good, The Bad, The Crazy

So, I don’t have a boss.

Whenever I meet someone new and tell them I’m a freelance journalist, they ask what that’s like. I always quote David Carr and say, “It beats working for a living!” and mostly leave it at that. But I’ve been thinking about the real answer.

I tell people what I do for a living and I know it sounds luxurious as hell. I can go hiking on a Tuesday afternoon. Last Thursday, I wrote a story in the car on the way to the Poconos and then skied for hours. I wear pajamas almost all day, almost all the time. Whenever I want a peanut butter and fluff sandwich, I can get up and go make one. In my pajamas.

And that stuff is all definitely awesome. But when I started this whole full-time freelance journey a few months ago, somehow I thought it would go a little… I don’t know… smoother? It’s been a pretty bumpy ride.

Let’s start here: I’m still super poor. In some ways, this is incredibly motivating. When I do sell a high-dollar story, it’s the biggest deal, and totally worth celebrating. I spend a lot of time chasing that feeling, and when I eventually make enough to cover my rent it’s so satisfying.

The other side of that coin is, of course, the part where I’m super poor. So far I haven’t established what I’d consider a “regular income,” and that’s constantly anxiety-inducing. There are a lot of days when this feels like a pipe dream, and like it’d be much easier to go back to riding a desk. It also means I’m often tempted to take jobs that pay far less than I know I’m worth, or write things that don’t totally line up with my tenets of journalistic integrity.

Then there’s the crazy. Being a freelancer means strapping in to an emotional rollercoaster every single day. I devote hours to mining freelance job boards, researching stories and pitching editors. It’s like going on a dozen job interviews in an afternoon, and a lot of my emails never even get responses. A lot of great ideas go to waste, and it’s easy to get disillusioned with the process.

But then – then – somebody says yes, and I get to do a great interview, write a great story and know people are reading it. And on those days, it’s all totally worth it.

Plus, honestly, my dogs have the best life.

Olive the Happy Hiker
Olive the happy hiker on the Appalachian Trail

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