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Business of Freelancing

Friday, January 24
1-4 p.m. EST

Led by ALI FRANCIS
with guest panelists Jess Tran, Elyse Inamine, and Chloé Caldwell

$110

Register

This course offers a transformative, holistic approach to the business side of freelancing, providing writers with the essential tools to manage finances, adapt to changing technologies, secure higher rates, develop steady income streams, and market themselves in what feels like an increasingly crowded space.

A successful freelance writing career comes with its own unique challenges—whether you’re just breaking into the market or looking to level up. Most freelancers are handling a lot: pitching ideas in a competitive industry while maintaining creative energy for longterm projects, financial stability, client relationships, and some semblance of work-life balance. The path can be daunting. But with the right strategies and support, you can craft a thriving freelance business on your own terms.

Over the span of this three-hour session, you’ll learn about the various ways writers can make money—covering everything from pitching articles to top-tier publications to writing branded content, crafting compelling copy for businesses, and taking on random side gigs to pay the bills. You’ll discover how you can structure your business setup to minimize tax liability and maximize earnings, what it takes to secure ongoing contracts and retainers for steady income, and how to create more time for the work that most inspires you. 

In a 60-minute panel discussion, you’ll also hear from seasoned freelancers Jess Tran, Chloé Caldwell, and Elyse Inamine. They’ll share candidly about how they make money—from landing retainer clients to diversifying income streams—as well as their key mistakes, lessons learned, and actionable tips for negotiating rates, managing clients, and sustaining a solid freelance career.

Students will learn to:

  • Hone their skills in setting rates and negotiating contracts that reflect their value—as well as legal clauses to watch out for 

  • Market themselves as standouts in a competitive field through branding, positioning, and strategic networking

  • Diversify their income streams, explore unique revenue models, and build a business that succeeds creatively and financially

  • Master the delicate balance between maintaining a consistent workload and protecting creative energy

  • Set up their business for tax efficiency and income optimization, including managing quarterly taxes, maximizing deductions, and more

  • Develop systems for productivity and time management to stay on track with deadlines, juggle multiple projects, and avoid burnout

This course is designed as an engaging lecture-style session rather than a hands-on workshop. While we’ll collect student questions ahead of time (until January 17) to tailor the material, the focus will be on delivering actionable insights and strategies, rather than individual feedback or interactive participation. 

About the Instructors

Ali Francis

Elyse Inamine

Jess Tran

Chloé Caldwell

  • Ali Francis is a former food and culture reporter at Bon Appétit magazine with work published in New York Magazine/The Cut, The Atlantic, the BBC, The Guardian, TASTE, and more. She’s a founding editor of Best Food Blog, a writer owned newsletter about eating. And in addition to journalistic and creative writing, Ali has built a stable (sometimes even lucrative!) freelance career spanning creative direction, copywriting, brand strategy, and more.

  • Elyse Inamine is a writer and editor based in New York City. Previously, she was the restaurant editor at Bon Appétit, where she created Heads of the Table, a food industry leadership awards platform. Now she writes about food culture, chefs, and restaurants for Bon Appétit, the New York Times, TASTE, and more, and is working on a few cookbooks. 

  • Jess Tran is a Vietnamese-Australian photographer, writer, consultant, and creator based in Brooklyn, NY. She consults for progressive organizations via Vocal Media for Planned Parenthood, Nuclear Threat Initiative, and more; and is in the process of writing her first novel. 

  • Chloé Caldwell is the author of the national bestseller, Women (Harper Perennial, 2024). Chloé’s next book, Trying, is forthcoming from Graywolf, on August 5th, 2025. She is also the author of the books I’ll Tell You In Person (2016), The Red Zone (2022), and Legs Get Led Astray (2012). Her essays have appeared in the New York Times, Vogue, Bon Appétit, The Cut, Vice, Longreads, Nylon, The Rumpus, The Sun, and half a dozen anthologies including Goodbye To All That: Writers on Loving and Leaving NYC, Without A Net: The Female Experience of Growing Up Working Class, and Sluts.

Details

This course will take place on Zoom on Friday, January 24, 1 - 4 p.m. EST. Participants will receive a Zoom link prior to the course and a recording of the course afterward (those who register before January 17 will also receive a brief questionnaire). We cannot offer refunds once the course has begun. Please email courses@offassignment.com with any questions.

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