Ran Harpaz
1 min read
Healthcare remains one of the biggest hurdles before and after going solo, and knowing your options, from partner plans to group-style coverage, can make the leap feel far more manageable.
More than a third of solopreneurs say healthcare was one of their biggest hesitations before going independent, according to our 2026 Solopreneur Perspective survey of 603 businesses-of-one. The questions keep coming after launch, too, with 23% saying healthcare and benefits decisions have been harder than expected.
Many people know this pull as "healthcare handcuffs," the tie to employer coverage that keeps someone in a job longer than they'd like. The encouraging part? Health insurance for the self-employed has more paths today than ever, and this guide walks through what solos told us, the options available, and how to choose a plan that fits a business-of-one.
Lettuce can make the healthcare side of solopreneurship simpler, with group-rate coverage that helps you approach benefits with more options and less guesswork.
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Show savingsWhat You Give Up When You Leave Employer Coverage
Leaving a job usually means leaving its health plan, along with the employer contribution that quietly covered a large share of the premium. Going solo means picking up the full cost and every choice that comes with it.
Most employees rarely see how much their employer pays toward coverage. It shows up as a modest payroll deduction, while the rest of the premium is handled behind the scenes.
Group plans also come with built-in buying power. A large employer negotiates on behalf of hundreds or thousands of people, which tends to bring broader networks and steadier pricing.
As a business-of-one, you become your own benefits department. That's a lot of control, and it's a big part of the emotional economics of independence that every solo weighs before handing in their notice.
If you work in healthcare yourself, the decision can feel especially personal. Lettuce's page for independent healthcare providers covers the back-office side of running a solo or locum tenens practice.
What Solopreneurs Told Us About Coverage Before and After Going Solo
Healthcare weighs on solos before the leap and keeps coming up long after it. The survey shows clear hesitation beforehand and a noticeable value gap once people start buying their own coverage.
Before the Leap
36% of solopreneurs cited healthcare as one of their biggest hesitations before going independent. Among those who couldn't rely on a spouse or partner's plan, that number rose to 4 in 10.
Solos without a backup feel the stakes most. When every coverage decision falls on you, it's natural to want a plan in place before you make the move.
After the Leap
Once solos are covering themselves, the question shifts from access to value. Among all respondents, only 23% feel they have a good plan at a fair price, while 19% feel they have good coverage but are overpaying for it.
Another 24% are unhappy with their coverage and plan options altogether. Put together, those numbers suggest plenty of solos are still searching for the right fit.
The Partner Plan Pattern
29% of solos get coverage through a spouse or partner, the most common source in our survey. Among high earners making more than $151,000 a year, that share climbs to 36%, the highest of any income group.
So for many established solos, the healthcare handcuffs never fully come off. They're simply tied to a partner's employer now.
Health Insurance Options for the Self-Employed
Self-employed professionals typically get coverage through a partner's plan, the ACA Marketplace, a professional association, a private plan, COBRA, or group-style coverage through a PEO. Each one fits a different situation.
Here's how they compare:
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Coverage Option
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Where It Shines
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Trade-Offs to Weigh
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Spouse or partner’s plan
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Employer-subsidized premiums and familiar benefits
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Coverage depends on their job, and it can affect some self-employed tax deductions
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ACA Marketplace
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Open to individuals, with premium tax credits possible depending on income and current federal rules
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Plan choices, networks, and premiums vary by state, and net costs may be higher for some households now that enhanced subsidies have expired
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Professional associations
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Some offer group plans or member discounts for independents
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Availability, plan quality, and cost vary widely by association and state
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Private individual plan
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Direct choice of carrier and plan design
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You typically pay the full premium without group pricing
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COBRA
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Keeps your former employer’s plan in place for a limited time
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Temporary, and you generally pay the full premium plus an administrative fee
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Group-style coverage through a PEO
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Access to group-rate plans usually offered by larger employers
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Eligibility often depends on business structure, payroll setup, and location
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There's no single best option for every solo. The right fit depends on your household, your health needs, your state, and how your business is set up.
What's Changing for Independent Workers in 2026
A growing category of group-style benefits is opening up to independents. Professional employer organizations (PEOs) now let some businesses-of-one access pooled coverage that used to require a full team.
A PEO uses a co-employment model to handle payroll and benefits for the businesses it serves. Mid-sized startups have relied on PEOs for years, and the same model can now work for a company of one.
A few factors typically shape access to group-style coverage as a solo:
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Business structure: Many programs require you to run W-2 payroll, which often means operating as an S Corp.
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Location: Plan availability can vary by state as providers expand.
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Enrollment windows: Coverage often starts on set enrollment dates, so timing matters.
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Plan design: Networks, prescription coverage, and cost-sharing differ from plan to plan.
Lettuce is one example of this shift. Our PEO gives eligible Lettuce Pro members operating as S Corps access to group-rate coverage from Curative, currently available in select states, and you can see Lettuce's healthcare options to check availability where you live.
How to Evaluate a Health Plan as a Business-of-One
Start with three things: what you can afford over a full year, whether your doctors are in network, and how your premiums are treated at tax time. This short checklist keeps the comparison simple:
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Set your cost ceiling. Add a year of premiums to the plan's out-of-pocket maximum to see your realistic worst-case spend.
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Check the network. Confirm your doctors, specialists, and prescriptions are covered before you enroll.
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Understand the tax treatment of premiums. Self-employed people may be able to deduct health insurance premiums, subject to IRS rules. If you operate as an S Corp and own more than 2% of it, premiums paid or reimbursed by the business are included in your W-2 wages, and you may then be able to claim the deduction on your personal return, depending on your situation.
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Review your business structure. Once your business consistently earns $70,000 or more a year, an S Corp may help lower self-employment taxes and open the door to payroll-based benefits. Lettuce Pro comes with the Lettuce-Back Guarantee, so if it doesn't save you more in taxes than it costs, your subscription fees are refunded.
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Plan for life changes. If you rely on a partner's plan, keep a backup option priced and ready in case their job changes.
Healthcare and taxes are closely linked for solos. We dig into tax strategy, S Corps, and retirement in our guide to navigating finances solo.
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Take QuizCommon Questions About Health Insurance for Solopreneurs
Shopping for coverage on your own brings up plenty of questions. Here are straightforward answers to the ones solos ask most.
Can freelancers get employer-style health insurance?
Yes, in some cases. PEOs and some professional associations offer group-style plans to independents, with eligibility based on factors like business structure and location. Eligible Lettuce Pro members operating as S Corps can access group-rate coverage through Lettuce's PEO in select states.
Is health insurance tax-deductible for the self-employed?
It may be. Many self-employed people can deduct health insurance premiums, up to the net profit of their business, and are subject to IRS rules, including not being eligible for a subsidized plan through a spouse's employer. For S Corp owners who hold more than 2% of the company, premiums paid or reimbursed by the business are included in W-2 wages. A tax professional can help confirm how the rules apply to you.
What's the cheapest health insurance for solopreneurs?
It depends on your income, state, and household, so there's no single cheapest option. Price is a common sore spot, with 19% of solopreneurs in our 2026 survey saying they have good coverage but are overpaying. Comparing total yearly cost, including premiums and out-of-pocket limits, gives you the clearest picture.
How do most solopreneurs get health insurance?
In our 2026 survey, the most common source was a spouse or partner's plan at 29%, followed by the ACA Marketplace at 26%. Others use private plans, COBRA, or other arrangements, and some currently have no coverage at all.
Is healthcare a big reason people hesitate to go solo?
For many, yes. 36% of solopreneurs named healthcare as one of their biggest hesitations before going independent, rising to 4 in 10 among those who couldn't rely on a partner's plan. Planning your coverage early can make the leap feel much more manageable.
Find Coverage That Fits the Business You're Building
Healthcare may be one of the toughest pieces of going solo, and it's also one where good information goes a long way. Knowing what you're leaving behind, comparing your options clearly, and choosing a structure that supports you can turn coverage into a decision you feel in control of.
The full Solopreneur Perspective 2026 report shares more of what 603 solos told us about healthcare, finances, AI, and growth. Download the full report to see where your own healthcare journey fits.
Lettuce makes healthcare easier to factor into your business planning, with solutions designed to simplify coverage and the costs that come with it.
Lettuce offers health benefits to eligible Lettuce Pro members through its professional employer organization (PEO). Health/medical coverage is provided by Curative. This article is for informational purposes only and does not constitute medical, insurance, tax, or legal advice. Benefits, plan availability, coverage, premiums, eligibility, and potential savings vary by state and individual circumstances and are subject to change. Coverage is subject to the terms and conditions of the applicable benefit plan. Nothing in this article should be interpreted as a recommendation to purchase, enroll in, or decline any specific insurance plan. Consult a licensed insurance agent, tax professional, and/or healthcare provider before making decisions about your health coverage or benefits.
