Navigating Open Enrollment and Health Insurance For Solopreneurs and Freelancers
If you're navigating health insurance on your own, the choices can feel overwhelming — plan types, networks, premiums, and tax implications all matter.
Open enrollment is here (opens on Nov 1) and it’s more confusing than ever to pick the right insurance plan for your needs and your budget. Plus, almost anyone who has useful information is trying to sell you something, which means it's hard to know who to trust.
Join Stefanie Lau, a lead for the 35,000 Xoogler community, and Alex Hillman, the founder of Indy Hall and a 20+ year advocate for solo careers and independent work, for a practical discussion on the reality for solopreneurs and small business owners like you.
This practical discussion will help you better understand the often invisible options to access and afford high quality healthcare, how to think differently about your premiums and deductibles and out-of-pocket limits, how to leverage HSAs. You'll even learn some
"secret handshakes" with medical provider offices to lower the total cost of coverage for yourself AND your family.
Bring your questions, and anything we can't answer we'll try to direct you to the most trustworthy resources we know. The goal is to leverage our collective wisdom to get a better grasp of your to needs and help you find the best coverage options for you.
How to get the most out of this chat:
Bring your healthcare bills from this year
Make a reasonable estimate of your 2026 income, and
Bring your top questions.
This event is both virtual and in person at Indy Hall in Philadelphia.
Important:
No sales pitching benefit plans — no one here sells benefits.
This is only advice based on the experience of people in the room, and we are not licensed agents or providers. It should inform, but not direct your decisions. You should make your own choices based on all the information you’ve gathered through your research.
Open to anyone having to navigate US open enrollment.