Flying Solo

Flying Solo

A six-week intensive designed to help you build a sustainable (and fun!) freelance journalism career

When people hear that we’re full-time freelancers who make a real living, they always want to know how. How do you get enough work to pay the bills? How did you break into your dream publications? How do you develop relationships with editors so that you’re not constantly cold pitching? How do you plan your finances so that you don’t run out of money the week before rent is due? Perhaps most importantly, how in the world do you think about your career in the long- or even medium term when you don’t even know what you’ll be working on next week?

In this six-week online class, we’ll spill all our secrets. We’ll teach you how to find the kinds of story ideas editors are dying for; where to find easy, lucrative work to subsidize your journalism; and how to actually manage your money. We promise to talk about the nitty-gritty details everyone always glosses over: exactly how much money Publication X pays, what big-shot editors’ pitching pet peeves are, whether you need to pay quarterly taxes, and how journalists break into books, podcasts, and TV. Along the way, we’ll bring in some of the smartest folks in the business — including editors, other successful freelancers, and even our accountant — to answer your specific questions and provide direct feedback. In addition to the six sessions, you’ll also get a one-on-one coaching session with one of us to talk through anything from a pitch to a career plan, as well as a packet of resources including successful pitches, an invoice-tracking system, and more. You’ll leave the course with a clear set of goals, a financial organization system, strategies for effectively pitching editors, and a cohort of new colleagues.

Our winter 2026 class is full. Sign up below if you’d like an email when we open registration for the next round.

HEAR ABOUT FUTURE CLASSES

Who is this for?

This class is targeted toward people with substantive journalism experience who are looking to level up their freelance journalism careers or are currently in staff jobs and hoping to go freelance. Since we both largely write reported stories rather than essays, it’ll be most helpful to you if you’re interested in that, too. It is not designed for people new to journalism, looking for new staff jobs, or who primarily want to support themselves through copywriting, marketing, ghostwriting, etc.

What does the class include?

  • A six-week course on the nitty-gritty of freelance journalism (see schedule below)
  • Guest speakers including editors, other successful freelancers, and our life-changing accountant
  • A one-on-one coaching session with one of us to talk through your story ideas and/or career plan
  • A packet of resources including successful pitches, an invoice-tracking system, and more
  • A WhatsApp group of your colleagues

When is it?

The upcoming class will take place on Zoom for six weeks, from 4-5:30 pm EST every Wednesday. These are the dates:

  • January 21
  • January 28
  • February 4
  • February 11
  • February 18
  • February 25

We’ll schedule your one-on-one coaching session for a time during that six-week period.

Our winter 2026 class is full. If you’d like us to email you when we open slots for the next class, sign up for updates here.

What does it cost?

The fee for Flying Solo is $600 per person.


We also set aside three discounted seats in each workshop at $200 each. These spots are designed for people who are from backgrounds underrepresented in journalism and who do not have the financial means to pay the full cost of the workshop.

Who are we?

Megan Greenwell is the bestselling author of Bad Company: Private Equity and the Death of the American Dream. A longtime editor and newsroom manager turned freelance writer, she writes narrative features about business, higher education, and public policy for Bloomberg Businessweek and other publications, hosts “The Kicker” podcast for the Columbia Journalism Review podcast, and works as a consultant to newsrooms who need help solving problems. She has taught journalism at Syracuse and is the deputy director of the Princeton Summer Journalism Program. Before freelancing, she wrote, edited, or managed people for publications including The Washington Post, ESPN, New York, Deadspin, and WIRED. She lives in Brooklyn.

Charley Locke is a contributing writer at The New York Times Magazine who often covers what it’s like to grow up and grow old. She also contributes to travel guidebooks, produces video and on-stage stories, writes for publications including The Atlantic and Vox, and edits the website of the UC Berkeley Center for the Science of Psychedelics. Charley teaches at the Princeton Summer Journalism Program and edits incarcerated writers with Empowerment Avenue, and previously taught writing to students in Oaxaca, Mexico and Shōdoshima, Japan. Before freelancing, she worked at Pop-Up Magazine, Texas Monthly, and WIRED. She lives in Portland, Oregon.