Health insurance for Substack writers

Introducing Substack Health

When I was a freelance journalist a few years back, health insurance was a source of mystery and pain. I didn’t really understand the U.S. healthcare system and quickly realized I couldn’t afford anything other than the “Sigh... We Guess We’ll Reattach One of Your Arms After a Catastrophic Car Crash” plan. Even with insurance, my primary health plan was to try not to get sick.

My experience wasn’t at all unusual. We’ve seen at Substack that uncertainty around health insurance is often enough to prevent writers from going independent. Health care—or lack thereof—is just one more stress that an independent writer really shouldn’t have to deal with. So we’re trying to do something about it. 

For the last year, we’ve been piloting a program to subsidize health care for a small number of writers and connect them with plans that they own and control. Today, we’re dramatically expanding the reach of the program. 

We’re partnering with HealthSherpa to make it simple for any Substack writer to find a health insurance plan that works for them. HealthSherpa understands the specific concerns and needs of Substack writers and provides customized support, all through a user-friendly interface. 

To kick start this new program, we will offer a one-time $500 health stipend to any U.S. writer who pays out of pocket for health insurance and has more than $5,000 in gross annualized revenue on Substack. You can read more about the program and apply via (Applications are open until January 20, 2022 at 11:59pm PT.)

This initiative is one of many services we’re testing and expanding, including investments in legal support, design, editing, and financing. Our goal is to remove the barriers for writers to go independent and help recreate some of the support structures that are otherwise disappearing from the media landscape. We welcome your feedback, ideas, and interest in collaboration as we develop these programs and expand the impact of this work.

Learn more about Substack Health at