Why Defining Your Values Will Help You Build a Sustainable Freelance Writing Business

Jenni Gritters
5 min readFeb 24, 2020

Now that you’re your own boss, you need to knowing what you care about at work

I first tried freelancing in 2015. I was so burned out by my journalism job that I needed an escape, fast. I had no prospects but I needed to get out for my mental health, so I quit and decided that freelancing seemed like a great route toward freedom.

I wasn’t wrong; freelancing is a great route toward freedom. But during my first try as a freelancer, I couldn’t make the lifestyle work. My husband was between jobs and our state-sponsored health insurance was incredibly expensive. I wasn’t making enough to support my husband and me, let alone cover the costs of health insurance. I also didn’t know how to navigate my schedule now that I was on my own, so I ended up taking on work I didn’t love and working crazy hard for a few weeks before I crashed. In other words, I was trying to apply the strategy I knew from my former full time jobs: Work hard, get noticed, and eventually the work will become more interesting and lucrative as I make my way up the career ladder.

The thing is, freelancing doesn’t really work like that, so it didn’t work for me during round one, either. Instead of sticking with it, I got a full time job again. But the thing was, I loved the freedom of time associated with being a freelancer. While I hacked away at my salaried editor job, I realized that I kind of missed it. So when I got laid off from that job, I had a decision to make: I could look for more full time jobs, but I could also try to go back to freelancing.

Although it took a while to make a decision, I knew in my heart of hearts that I wanted to freelance. But I was nervous, so I felt like I couldn’t make the jump! After all, it hadn’t worked before, and I didn’t think people would take me seriously. Fast forward to a very good appointment with my very smart therapist, where she encouraged me to create a business plan for myself.

“What if you could create your dream job?” she asked me.

In the end, the was right. Making a plan helped me feel like I could make freelance journalism my career, not just my side hustle.

Jenni Gritters

I’m a writer and business coach for freelance creatives based in Central Oregon. I write about the psychology of small business ownership.