Publishing | Bootcamp

2-Day Publishing Bootcamp: Everything You Can't Google About Freelancing

Freelance writing is a mysterious gig. How do you get your pitches accepted? How do you ask for money—and how much should you ask for? Most freelance writers learn this information through a frustrating process of trial and error. We don’t believe this process has to be so harrowing. Our class aims to simplify the process, to get your pitches out of the slush pile, and teach you how to learn from the inevitable rejections (yes, it truly happens to everyone). Freelance writing can be difficult, but it can also be a source of immense satisfaction.

Jamie and Leah are a writer/editor team. We’re friends, but we’ve also worked together. Sometimes we argue and sometimes we agree. In any case, you’ll reap the benefits of our dual perspectives.

Our class doesn’t promise any magical solutions or surefire ways to land a cover story. But we will provide you with reliable skills that have served us well in this volatile industry. If you take our class, here are some things that will definitely happen:

- You will write at least one incredible pitch

- You will find out which publications best fit your ideas, and how to find editors to pitch to

- You’ll learn what to do once it gets accepted (including, but not limited to, how to ask for money and make sure you get paid!!)

- We’ll dissect some bad pitches and tell you why they failed

- We’ll dissect some great pitches and take a look at the stories they became

- We’ll give you tips on how to survive as a freelancer

- You’ll leave with a game plan for how to accomplish your publication goals

This two-day bootcamp will also include a long and fruitful Q&A session. If you’re tired of romantic, wishy-washy advice, we promise that this is the class for you.  

Jamie Lauren Keiles

Jamie Lauren Keiles is a contributing writer for The New York Times Magazine. They have been freelance writing full time since 2015. 

Leah Finnegan

Leah Finnegan is a features editor at The Outline and the author of Leah Letter, a semi-monthly media criticism newsletter. She previously edited at Gawker and The New York Times. She accepts or rejects about 400 pitches each month. 


“Some freelancers are guarded and strange about their processes—where they find their ideas, how they pitch their editors, what they do on or just past deadline. JLK is not. She is frank and funny and open and honest. Also: the best person for commiserating about a career in freelance writing.”

Ryan Bradley freelance feature writer

“As an editor Leah Finnegan makes you a clearer and more thoughtful version of yourself, she is one of the sharpest I’ve ever worked with.”

Kelly Conaboy freelance writer