Taking Care of Business…with Carolyn Bothwell

We’re passing the mic to some of our favorite freelancers who make Wingspan’s community thrive, and who remind us every day that there are no wrong ways to take care of business. Want to be featured next? Nominate yourself here!

Carolyn Bothwell is a Boston-based brand strategist and copywriter. When she’s not consulting for clients like Hilton, TripAdvisor, GILT, Wayfair, and Living Proof, she’s running an online community for creative and marketing pros called Freelance Founders. She shares the podcast that sparks inspiration, the best advice she’s ever gotten, plus the mindset freelancers must have to succeed.

In your own words, what do you do? 

I’m the Founder of Freelance Founders. And,I’m also a freelance brand strategist and copywriter. 

Where do you call home? 


What’s the first thing you do when you wakeup? 

The first thing I do is take my dog out. Then, coffee. 

What’s your favorite thing about freelancing?

I love the freedom and flexibility to choose my projects and work on my own schedule. It’s really motivating to be directly responsible for how much money you make. And I’m forever inspired by the founders and creatives that I get to work with. 

What’s the best advice you’ve ever gotten? 

It’s cliché, but truly, trust the process. True life: I almost stopped copywriting to go into commercial real estate. Got rejected. Joined a random startup. Starting freelancing as aside-hustle. Quit said job. Now, I’ve been freelancing full-time for 3+ years.

What’s your biggest challenge as an independent professional? 

Personally, anything financial is a struggle for my right-brained self. But I’ve been fortunate to be able to work with a trusted team of advisors and accountants. 

[Shameless plug: Wingspan’s platform streamlines invoices, benefits, and bookkeeping—all in one place. Sign up for your 30-day trial.]

What’s your favorite freelance project you’ve worked on? 

Freelance Founders. There’s nothing better than being your own client. 

What’s your best hot take / unpopular opinion? 

Freelance is the future. Sorry, agencies—still love you!

What do you wish you’d known 10 years ago? 

Creative careers are a thing. And you can actually make money doing what you love.

Most iconic work role model? 

Pandora Sykes. If you haven’t read her book, How Do We Know We're Doing It Right? add it to your list STAT.

How do you deal with difficult clients? 

I always try to open the dialogue and get to the heart of the issue. But I’ve learned the hard way that sometimes it’s just not a good fit. The best thing about being your own boss is that you can (and sometimes, should) walk away. Try to identify red flags before you ever say yes to a prospective client.

What—or who—is your go-to source for inspiration? 

Online shopping for art that I can’t afford. Armchair Expert, the Dax Shephard podcast, always sparks some new curiosities.

Best workday lunch? 

It’s a local Boston spot (and past client): Mother Juice. Truly anything on their menu makes for the best lunch.

What’s your anthem? 

Sarah Saxty, founder of Reality BitesSocial Club, has curated the most incredible productivity playlist. Attend one of our virtual co-working sessions to listen for yourself. 

What is the best freelancing pro tip you have for folks venturing out on their own? 

Think of yourself as the founder of your own business, not a contractor. Set up a legit legal entity, get a business bank account, make a logo, and a website, save money for taxes, use contracts, consult lawyers as needed. It’s a shift in mindset that really helped accelerate my freelance business.

What’s your email sign off? 

“Talk soon!” Got to keep that network strong as a freelancer, ya know?

Where can people find you?  

@by.carolynbothwell on IG and www.carolynbothwell.com

Want to share your freelance journey with the Wingspan community? Submit yourself here.

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