My First Six Months Freelancing

What freelance life really looks like: Otis and I putting in that work.

What freelance life really looks like: Otis and I putting in that work.

I entered the world of full-time freelancing the same way you jump out of an airplane: With a lot of fear, overpowered by a lot of faith.

I’ve wanted to be a freelancer for as long as I’ve wanted to be a writer, but I was never 100 percent sure I could hack it. The complexities and struggles of freelancing are well-documented and depressing, and I spent years bouncing between, “I have what it takes” and “I absolutely do not have what it takes, who the hell do I think I am?”

But in mid-2018, I jumped. I had spent the past nine months working 12-hour days—three hours at a coffee shop, nine hours at my corporate job—and it was finally time to just do the damn thing. I had a roster of clients. I had a financial plan. I had a marketing strategy. I had an embarrassing amount of affirmations scribbled in the margins of my journal. I was ready to exit the aircraft, and I was taking my industrial-sized parachute with me.

Though freelancing has not been easy, it has been very exciting. Unscalable walls have given way to wide-open spaces. I feel so engaged in my day-to-day again. I want to write really good shit again. I want my business to prosper.

There is still much to learn, but I’m proud of what I’ve accomplished so far. Here are some highlights from the first six months:

  • I had a number of regular clients before I went full-time, including Parks for Downtown Dallas, a nonprofit foundation bringing four new parks to the city. I’ve written their blog and much of their social media since November 2017, and I enjoy how this account keeps me connected to the local scene, while also expanding my knowledge of environmentalism and urban planning.

  • When I left my job as Senior Editor at the ACTIVE Network, I continued to write for Funny enough, it wasn’t until I went freelance that I had one of my biggest hits to-date: An Ode to Slow Runners. I want to thank everyone who reached out to me on social media to talk about the article—I had a lot of fun writing it!

  • My job at ACTIVE also put me in a prime position to write health and wellness content. Much of this work isn’t available online but covers many topics. Think everything from eye health for contact wearers, to forming better Sunday night habits, to keto-friendly avocado recipes.

  • I wrote two features for SPARK Magazine, which is produced by the Dallas Market Center and illustrates how some B2B work can feel extremely B2C (but with a significant pay bump, no less!). Whether it was for my roundup on give-back brands or my profile on Western craftsman, Clint Orms, each person I interviewed had such reverence for their art. It was deeply inspiring.

  • I also worked closely with Amber LaFrance and the team over at CultureHype on their website relaunch (coming soon!). This was my first major branding project, and I loved how free and creative it felt. I’m now interested in how I can work more branding services into my business.

  • Toward the end of the year, I also started working with Under Armour. I kicked off by tackling a big deliverable: MyFitnessPal’s 2018 Holiday Gift Guide. I now write for their Victory Stories section (examples here and here) and am honored to have others share such personal histories with me.

  • Finally, I negotiated more contracts than I can count, which is easily the hardest thing I do each month. I really try and walk the walk here, asking for higher rates 90 percent of the time and turning down some projects altogether. It is scary and hard and, frankly, kicks up a lot self-doubt, but it has been ESSENTIAL for being able to afford my rent, not to mention health insurance, quarterly taxes, self-funded retirement contributions, etc.

In 2019, I’m excited to expand to other niches and hopefully write more for traditional publications, now that I have some financial footing in the content marketing world. I also still have a few weakspots I’d like tackle—pitching, direct client contracts, being in any way consistent on social media (a nightmare, I tell you)—so I’m hoping this year provides the opportunity to do so.

Jackie Velingroundup