5 Lessons From My First Year of Full-Time Freelancing

I’ve arrived at the proverbial place — that place in my career where everything’s come together, and all the obstacles that have preceded it make sense. Finally.


In October 2020, I was pandemic-furloughed from my position as content marketing manager at Cincinnati Playhouse in the Park. I was asked to return to my position last March, but by then, I’d already established a foundation as a freelance writer and storyteller. It’s been years in the making: For the past decade, I’ve either hustled or side-hustled as a copywriter, video producer, screenwriter, content marketer and ghostwriter. That decade also includes three years of graduate film school and four years of a full-time job with the Playhouse. One of my clients from a few years ago hit the nail on the head when he (respectfully) told me, “Damn, you don’t rest much, do you?” Until this point, no.

Now, as I wrap up my first nine months of building my freelance business, I’m heading into 2022 with a lot more wisdom. Here are some pearls I’ve taken away.

Work begets work.

Freelance can sometimes be “feast or famine,” and that was certainly true for the first few months. It was daunting to begin a new work week if I didn’t have a full workload. And if I was in the midst of a project or assignment in which I was waiting for responses, I still had to fill that time with some kind of work — networking, branding, blogging, applying to freelance and contract positions through LinkedIn, connecting with staffing agencies, etc. Unlike a salaried position, the occasional light workday doesn’t mean I can relax. It actually means the opposite. If I have a light day without guaranteed work coming up, I need to be generating work energy.

Being the boss (instead of having one) changes everything.

I’ve shifted my focus away from being an employee of someone’s company and solidly towards running my business. I carry myself with more confidence, I thrive when I can manage my own schedule and workload, and I have a constant rush of energy for creative strategy. I also love being able to answer, “What do you do for a living?” with, “I’m a professional writer.” I have been for a decade, but to say that in its wonderful simplicity without adding a full-time job title and explaining that I side-hustle my writing is incredible.

My health has improved dramatically.

I had always hoped this would happen. I wasn’t certain it would, but I’m so grateful that it has. The ability to control my work schedule has eased so much of my anxiety-related health challenges. I sleep better, I have more flexibility to schedule doctor’s appointments, I eat healthier because I’m at home, I can arrange workouts around my schedule, and I’m really just happier overall. Even when work-related stress hits, it passes so much faster than when I worked in an office. I’m also a homebody. It’s my second-best happy place — the first being a bookstore cafe where I can stack up a bunch of books and test the limits of my personal caffeine intake.

Working from home has made me a better (and faster) writer.

This seems like a no-brainer. I read and write for a living. I need quiet. Plus, if I ever have writer’s block, I can more easily untangle those knots while doing menial tasks around the house. Having this kind of solitude and being able to work through roadblocks in my own weird ways have sharpened my writing process.

My professional village is absolutely essential.

Solitude is beneficial when I’m working on projects, but when I need to plan for the future, gain insight, or just vent, I reach out to my village of fellow freelancers and folks who are doing similar work as me.

  • Rebecca Koch is a marketing pro and wellness expert who I became friends with in college. She and I have a Zoom call once a month to discuss our experiences in the marketing world and keep each other motivated about business development and brand-building. She’s a personal trainer, too, so her encouragement and accountability go a long way.

  • Samantha Parker is a longtime friend whose own business model has inspired me greatly — she doesn’t take on more work than she needs, making her client focus more streamlined and meaningful. She’s a digital copywriter, business consultant and project manager. I’ve never met anyone who solves problems as easily and as calmly as she does. She’s my go-to contact for workshopping ideas, gaining significant feedback and reminding myself what I’m doing and why it matters.

  • Aly Gomez is a digital marketing strategist with Capacity Interactive who I worked with at Cincinnati Playhouse. She quickly became my “work sister,” as we collaborated almost every day. She’s inherently influential to me because she has a high professional standard for herself and she’s just as detail-obsessed as I am. She also operates with a minimalist philosophy that’s been eye-opening when it comes to workflow and project management.

Truly, I could go on and on about even more folks in my network who have influenced, inspired and supported me. (Currently creating a post-it note for a future blog post on that.) If you’re venturing into the freelance world, get yourself a professional village of wonderful people.


Nine months have passed since I started to freelance full-time — with many, many more to come. Happy New Year, dear reader!

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