Health Insurance for Self-Employed, Freelancers & Creators

When you work for yourself, your health coverage should move with you—not hold you back. True North Associates helps self-employed professionals, freelancers, and creators compare their health insurance options, navigate enrollment, and avoid expensive gaps. Whether you’re in on the east coast, west coast, or working remotely across state lines, you’ll get expert support for every step—so you can focus on your work, not on insurance headaches.

Black eight-pointed star with a white dot in the center on a white background.

Insurance Options Designed for Self-Employed Life

Marketplace plans, private coverage, and creative combinations—your choices are broader than most realize. We walk you through year-round enrollment options, explain how income affects your eligibility and subsidy, and show you which plans are best for variable cash flow. You’ll know the trade-offs of each route (Marketplace, short-term, indemnity, or combo), and get clarity on what’s covered, what’s not, and how to avoid surprise expenses.

How We Help: Flexible Coverage for Every Scenario

Income That Changes Month to Month

Your plan should flex with your income—not the other way around. We help you structure coverage that adjusts as your revenue shifts, factoring in cash flow, risk tolerance, and the realities of business ownership.

Contract Gaps and Off-Seasons

If your workload (and income) is seasonal, we build strategies for the slow months—making sure you stay protected even when you’re between projects or contracts.

Family and Team Considerations

Need coverage for a spouse or business partner? We guide you through all the options, including how to compare self-only vs family plans and set up coverage if you expand your team.

Black eight-pointed star with a white dot in the center on a white background.

Adviser-Led Plan Design & Ongoing Reviews

You shouldn’t have to become an insurance expert just to run your business. Our adviser-led process means you get a side-by-side plan comparison (including compliant and non-compliant options), candid guidance on exclusions and renewals, and help with all paperwork. As your income and business change, we check in with you annually to make sure your plan still fits—so you can stay focused on your goals.

A woman is reading a book to a little girl
A family is walking through a field holding hands.

Your Questions, Answered

  • How do freelancers get health insurance?

    You can choose from ACA Marketplace plans, private options, or a spouse’s coverage if available. We help you compare based on your income, prescriptions, risk tolerance, and work habits to find the right fit.

  • Can I buy health insurance any time of year if I’m self-employed?

    Many private and short-term plans offer year-round enrollment. Marketplace plans have set windows, but qualifying events (like business launch or losing coverage) may open special periods—ask us to check your options.

  • What if I don’t qualify for a subsidy?

    We’ll help you weigh the real costs and explore private alternatives if Marketplace premiums are too high. Some self-employed clients blend plan types to balance cost, risk, and coverage.

  • Is short-term insurance worth it for freelancers?

    Short-term plans can fill gaps between contracts or for off-seasons, but they aren’t for everyone. We make sure you understand the benefits and limitations so you can decide with confidence.

Flexible Health Coverage for Independent Workers

Get health insurance that supports your business, your cash flow, and your creative life. Book a call today to skip the research and find a plan that keeps you—and your work—moving forward.