Unlock the Secret Freelancer Enrollment Strategies for 2027 That Could Save You Thousands

Ever found yourself scrambling at the last minute when Open Enrollment hits? Yeah, me too—it’s like a race against the clock, but for your health! Starting November 1, most states roll out their health insurance marketplaces, giving us freelancers a limited window to lock in coverage for the year ahead. Deadlines can be a moving target depending on where you live, so pinning down those exact dates is key (because who wants to miss out?). But here’s the kicker: Freelancers Union isn’t just pointing you to the usual options—they’ve teamed up with partners offering flexible plans designed for the unpredictability of freelance life. Whether you’re after low premiums, personalized benefits, or seamless virtual care, there’s something tailored for you. Take a quick quiz to find your match, then dive into the rundown below to get the full scoop on these options. Ready to stop stressing and start planning? LEARN MORE.

Open Enrollment begins in most states on November 1. If you’re choosing your healthcare through the government’s marketplace, November through January is your opportunity to enroll in one of these healthcare plans. (Exact deadlines vary state by state, so be sure to double check the pertinent dates for your location.)

Freelancers Union also offers health plan options through our partners. Take this quiz to determine which might be right for you, and read on below to learn more about each of them.

Solo Health offers nationwide PPO plans with low monthly premiums, no-cost preventive care, and plans pay for 100% of covered services after your deductible is met.

Dedicated Webinars:
November 3 at 2 p.m. ET
December 1 at 2 p.m. ET

Or book a free one-on-one consultation!

Smirk Health personalizes benefits for freelancers around your needs and budget, starting at $20/month. Know what your benefit pays before every visit, see any doctor with no networks, and Ailene™, your AI Care Concierge, can book it for you.

**Currently available only in Arizona, Georgia, and Texas, with more states coming soon. Sign up for the Smirk waiting list to stay up-to-date on new states added** 

Dedicated Webinars:
November 9 at 12 p.m. ET

River Health combines virtual and in-person care, so you can connect with healthcare professionals when and where you need them. Members can manage healthcare needs through a streamlined digital experience, while maintaining access to real providers and clinics nationwide for $50 or $125 a month.

Dedicated Webinars:
November 17 at 11 a.m. ET

Opolis provides all the benefits of W2 employment, including affordable, premium group healthcare, payroll, tax compliance, and more.

Dedicated Webinars:
November 18 at 1 p.m. ET
December 3 at 6 p.m. ET

Catch simplifies federal and state marketplaces so you can easily browse and compare plans. 

Galileo offers on-demand telehealth with no co-pays or deductibles. Add on Galileo Medical Plus* for dental & vision insurance plus prescription discounts.

Any questions? Feel free to email us at membership@freelancersunion.org to chat with our experts.

*Rx, Dental and Vision are provided by New Benefits and not affiliated with Galileo Medical

Galileo facilitates access to online clinical telehealth services and secure messaging from independent licensed healthcare professionals. Galileo is not an insurance product, and the amounts you pay to Galileo and the independent healthcare professionals are not insurance premiums.  Dental Benefit is not available to VT residents.

The discount program provides access to the Aetna Dental Access® network, which is administered by Aetna Life Insurance Company (ALIC). ALIC does not offer or administer the discount program, and is not an affiliate, agent or principal of the discount program. Dental providers are independent contractors and not employees or agents of ALIC. ALIC does not provide dental care or treatment and is not responsible for outcomes.

This program is NOT insurance coverage and does not meet the minimum creditable coverage requirements under the Affordable Care Act or Massachusetts M.G.L. c. 111M and 956 CMR 5.00. It contains a 30-day cancellation period, provides discounts only at the offices of contracted health care providers, and each member is obligated to pay the discounted medical charges in full at the point of service. The range of discounts for medical or ancillary services provided under the program will vary depending on the type of provider and medical or ancillary service received. Member shall receive a reimbursement of all periodic membership fees if membership is canceled within the first 30 days after the effective date. Discount Plan Organization: New Benefits, Ltd., Attn: Compliance Department, PO Box 803475, Dallas, TX 75380-3475, 800-800-7616.

Website to obtain participating providers: MyBenefitsWork.com.