How Not to Make Money as a Writer: Carrie Rollwagen on Freelancing, Fiction and Imposter Syndrome

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On this week’s episode of The Localist, Carrie is joined once again by showrunner Michelle Phillips. Carrie and Michelle take a deep dive into Carrie’s experience as a freelancer, starting off with how she began writing, her first paid writing gig, and the fun party trick she learned at her first internship. Carrie then tells us about freelancing on the side while working full time, gives us a great analogy for writing fiction, and introduces us to NaNoWriMo. Carrie describes her process of getting freelance opportunities and gives tips for anyone beginning their freelance journey. Carrie and Michelle then get into the financial side of freelancing: establishing your rates, finding different ways to charge clients, and managing expectations (you might never be wealthy in this industry!). Carrie then gets real with us about the feasibility of making a living as a freelancer, the misleading nature of social media, and whether all the hard work and hustling pays off eventually. They wrap up the conversation with the double-edged sword of being your own boss, imposter syndrome, feeling like a failure, and whether the struggle between making art and making money is worth it.

Mentioned in this episode: 

The Florida Sun

Morning Joe

Sluggo’s in Pensacola

Rita Skeeter

Cary Norton 

Birmingham Post Herald 

Jonathan Benton, Bookseller


No Plot? No Problem! By Chris Baty

The Localist book 

Sri Koduri on instagram

Kevin Wilder 

The Tipping Point by Malcolm Gladwell 

Church Street Coffee and Books 


About Carrie

Carrie Rollwagen is host of the Localist podcast and cofounder of Church Street Coffee & Books. Currently, she works as Vice President of Strategic Planning at Infomedia, a web development company in Birmingham, Alabama. Find the Localist at @thinklocalist on Instagram and follow Carrie at @crollwagen.

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