Carolyn Bothwell Wants To Be Free

By Brett McKenzie on Apr 20, 2021

Ahead of her freelancing workshop, a writer/strategist shares her thoughts

After a year of the COVID-19 pandemic, there appears to be light at the end of the tunnel, but our industry has definitely changed. After so many of us received crash courses in working remotely, we're beginning to question if we need to go back into the office again at all. And others might be wondering if they even need to be working for a single company, remotely or otherwise. Whether it's by necessity or by revelation, the past year has introduced the world of freelancing to a growing number of creatives.

Copywriter and strategist Carolyn Bothwell already had several years of freelancing under her belt. Still, when the pandemic hit, she noticed a dearth of resources for people new to working for themselves. And so she created Freelance Founders, a community where the self-employed can support and learn from each other about every aspect of the business. 

Carolyn will be leading a three-day workshop series entitled "The Business of Being Freelance" on May 4–6 to help both those already in this world and those considering making the plunge. We caught up with her to learn about her own path, as well as what others might expect when forging their own.


First of all, how did you get into copywriting? It's generally not a career they teach you about in high school...

I always loved to read books and magazines as a little kid, and when I was a bit older, I thought I would probably pursue a career in publishing. I decided to major in English Lit and minor in writing in college. One summer, I got an internship at Rue La La in their creative department as a copywriting intern. Honestly, I had no idea what copywriting was at the time, but I absolutely fell in love with it.

I remember being fascinated about how much work and thinking goes into such a short piece of copy. To me, it was so much more challenging than writing the long-form pieces that I was used to. My start at Rue La La felt promising. The program was great with a lot of hands-on mentorship and training. After I finished the six-week, paid internship, I had a pretty good sense of what I would do professionally. I’m really fortunate for that.

Being on the payroll of a creative department is nice, but what made you dip your toe into the world of freelancing?

I fell into freelancing by accident, as many people do. I left my full-time job at Rue La La to pursue marketing at a startup. During my time there, I really missed writing, so I began to take on freelance projects alongside some past coworkers. I loved it. The opportunities kept flowing in, and it felt very entrepreneurial and empowering to choose what I wanted to work on, how much my work was worth, and to run a small side business. After about six months, I was making just as much money freelancing as I was at my full-time job, so I decided to quit and give it a try. I haven’t looked back since.

What would you say has been the best thing about going the freelance route?

It’s allowed me to meet and collaborate with people, brands, and agencies all over the world. I believe that working with new perspectives and processes on nearly every project has helped me grow professionally and personally.

Of course, you're more than just a freelance copywriter. Last year you started Freelance Founders, a community for those who have also gone into business for themselves. What was the impetus for this endeavor? 

Since day one of freelancing, I was surprised at how little information and resources were available for independent creative professionals. I learned everything — like setting up an EIN and choosing preferred payment terms — from other freelancers. I always paid it forward and helped many other creatives go freelance and set up their solo business for success — honestly, I had like three or more calls per week dedicated to this. So, the idea for Freelance Founders was always top of mind for me.

When the pandemic hit, I saw more people in need of a digital community and resource hub, and decided to launch Freelance Founders. If you’ve freelanced before, you know that going at it by yourself can get pretty lonely, and there’s a lot to gain from having a network. In our community, freelancers share job leads, contacts, templates, and even their pricing. There’s so much to gain from surrounding yourself with people in your space.

We’ve grown 40% each quarter since our launch. In some ways, I think the pandemic was the perfect time to bring people all over the world together digitally. We were all going through the same things and had a lot of the same fears and uncertainty. It’s been very comforting and encouraging to meet other creatives in the group.

"If you’ve freelanced before, you know that going at it by yourself can get pretty lonely, and there’s a lot to gain from having a network."

What are some of the biggest misconceptions that newcomers to the world of freelancing have?

I think many people who are new to freelancing imagine that there will be this wonderful work/life balance. But that’s often the biggest challenge. It’s hard to say no to opportunities and extremely difficult not to overwork yourself. I think you have to learn to embrace a work/life harmony and be firm with setting client boundaries and working hours early on.

On the flip side, I think so many people are intimidated by the business and finance side of freelancing. In the end, it’s pretty simple to set up a legal entity and business bank account and begin invoicing. You can outsource the areas that make you uncomfortable. I’ve used an accountant for taxes since day one! If you’re worried about the money, it’s definitely a business of relationships. If you’re kind, hardworking, talented, and willing to network, the jobs will follow.

Speaking of finance, let's talk numbers — or rather how are supposedly right-brained creatives who may have flunked high school math supposed to handle this side of the freelance game (asking for a friend)?

(laughs) Relatable! Numbers will never come easy to me. Luckily, you can use an accounting and invoicing system, like Quickbooks, that tracks your payments for you. I strongly recommend working with professionals like accountants and lawyers for taxes and contracts. It’s an added cost but will probably save you tenfold in the future. By hiring out, you can spend more time focusing on the things you’re good at, and the money usually evens out in the end.

With all of that in mind, what kind of creative is best suited for this upcoming freelancing workshop?

This workshop series is for freelancers who have a founder mindset. They view the creative work that they do as a business, and intend to follow this path for the foreseeable future.

I’m excited to share everything I’ve learned over the past 5 years in this 3-day series.


"The Business of Being Freelance" takes place virtually, May 4–6 from 1–2:30 PM ET. Tickets may be purchased for each individual day, or for the entire three-day workshop.






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