Health Insurance forSelf-Employed & Remote Workers
A practical guide to your options—whether you're between jobs, considering a role without benefits, or building a freelance career.
⚠️ Enhanced subsidies expired Dec 31, 2025. Congress is negotiating a potential retroactive extension.
Last updated: January 4, 2026
Source: KFF Analysis, October 2025
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Stride Health
Best for Freelancers
Built for self-employed workers. Helps estimate income and find the right ACA plan.
Get a QuoteeHealth
Compare All Options
See plans from multiple carriers. Good for comparing ACA, short-term, and other options.
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Official Marketplace
The official ACA marketplace. See exact subsidies and enroll directly.
Check SubsidiesJump to your situation
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January 2026: Enhanced Subsidies Have Expired
The enhanced premium tax credits that kept ACA costs low since 2021 expired on December 31, 2025. Congress is still negotiating a potential retroactive extension, but no deal has been reached yet.
For now, expect significantly higher premiums—about double what they were in 2025 for most subsidized enrollees. If Congress passes a retroactive extension, you may be able to get a refund or adjustment.
What to do: Check Healthcare.gov for current pricing in your area. If you're between jobs, the COBRA safety net strategy (below) is more valuable than ever.
TL;DR for Remote Workers & Freelancers
- ACA Marketplace plans are still your starting point—even with higher 2026 prices
- COBRA is a safety net, not a default—but the math has changed (compare carefully)
- Subsidies still exist—they're just smaller. Low-income earners still get help.
- Congress may still pass a retroactive extension—stay informed
- You have 60 days to decide—don't panic
This is general informational content, not medical or legal advice. Insurance rules vary by state, and your situation may differ—consult a licensed insurance professional for personalized guidance.
Disclosure: We may earn a commission from some links on this page. We only recommend options we'd suggest to a friend.
Leaving Employer Coverage
Lost your job or about to leave one
When you lose a job—whether you're laid off, quit, or your position is eliminated—your employer health coverage usually ends soon after. Coverage often ends at month-end, but some employers end it on your last day—confirm your exact date with HR.
Here's the thing most people don't realize: you don't have to figure this out immediately.
The COBRA Safety Net
When you lose employer coverage, you get 60 days to elect COBRA—and that election is retroactive. This means:
- You can wait and see what happens
- If you stay healthy for 60 days, you've saved money
- If something medical does happen, you can elect COBRA after the fact and it covers you
This gives you breathing room to research ACA options, wait for a new job's benefits to kick in, or make a thoughtful decision instead of a panicked one.
Your Best Path Forward
For most people leaving employer coverage, the ACA Marketplace is the right answer. Losing your job triggers a "Special Enrollment Period"—you don't have to wait for open enrollment.
Key insight: ACA subsidies are based on your projected income for the current year, not last year's taxes. If you're unemployed, taking a pay cut, or expect lower income, your subsidies could be significant.
What to do:
- 1. Get your coverage end date from HR
- 2. Don't elect COBRA immediately—use your 60-day window
- 3. Check ACA options within 30 days at Healthcare.gov
- 4. Compare the ACA plan cost (with subsidies) to COBRA before deciding
Remote Jobs Without Benefits
Evaluating roles that don't offer health insurance
Here's a reality of remote work: many remote positions—especially contract roles, startup jobs, or smaller companies—don't offer health insurance. This isn't necessarily a dealbreaker. But you need to factor it into your compensation math.
How to Evaluate the Tradeoff
Step 1: Know what coverage will cost you
Before accepting (or rejecting) a role without benefits, get real numbers. Go to Healthcare.gov and run the numbers based on the salary you'd be earning. With reduced 2026 subsidies, expect to pay $200-600/month for moderate incomes. Higher incomes may pay $600-1,200+.
Step 2: Do the real math
A job paying $80,000 with no benefits isn't the same as a job paying $75,000 with benefits. Calculate:
- • Remote job salary: $80,000
- • Minus health insurance (~$6,000/year for decent ACA plan): $74,000
- • Minus other benefits you'd lose (401k match, etc.)
Now you have an apples-to-apples comparison.
Step 3: Consider the non-financial factors
Sometimes the remote flexibility, the role itself, or the career opportunity is worth the benefits tradeoff. Just make sure you're choosing it consciously, not discovering the cost later.
The Good News
If you're earning a moderate income, ACA subsidies make individual coverage genuinely affordable. The myth that "you need employer coverage or you're screwed" isn't true anymore—it's just that most people have never shopped for individual insurance and assume it's unaffordable.
Freelance and Self-Employed
Building your own coverage as an independent worker
If you're building a freelance career, doing gig work, or running your own business, you're in the same boat as millions of other self-employed workers who get their own coverage.
Why ACA Plans Usually Win for Self-Employed Workers
For self-employed people, ACA marketplace plans have two big advantages:
Subsidies based on current income
If you're early in your freelance journey or have variable income, you may qualify for significant help. You estimate your income for the year, and subsidies adjust accordingly.
Premium tax deduction
Self-employed people can deduct health insurance premiums from their taxable income—this makes the effective cost even lower.
Tools Built for Freelancers
Stride Health is specifically designed for freelancers and gig workers. They help you estimate your income and subsidies accurately, find ACA plans that fit your situation, and track the health insurance tax deduction.
If you want to see the broadest range of options (including some off-exchange plans), eHealth shows you more carriers and plan types.
What About Health Sharing Ministries?
You'll see things like Medi-Share marketed as a cheaper alternative. A few things to know:
- • These are not insurance—they're faith-based cost-sharing communities
- • Pre-existing conditions are often not covered
- • There's no legal guarantee your bills will be paid
- • Most require lifestyle commitments (faith statements, no tobacco, etc.)
They can work for some people—particularly those who are healthy, have a faith alignment, and want lower monthly costs. But understand what you're getting.
Your Core Options Explained
Regardless of your situation, your options fall into a few buckets
ACA Marketplace Plans
Health insurance purchased through Healthcare.gov (or your state marketplace). Plans must cover essential benefits and can't deny you for pre-existing conditions.
Best for
Most people—especially if your income qualifies you for subsidies (which still exist, just smaller than before).
Avoid if
You have access to affordable employer coverage (yours or a spouse's) that meets your needs.
Watch out for
Network restrictions. Make sure your doctors are in-network before enrolling. Also: 2026 prices are significantly higher than 2025.
Typical cost
2026 reality: With reduced subsidies, expect $200-600/month for moderate incomes, $600-1500+ for higher incomes. Low-income earners (under 150% FPL) still get significant help.
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Short-Term Health Insurance
Temporary coverage designed to fill gaps. Federal rules limit plans to 4 months total (3 months + 1 month renewal), though this is currently under review.
Best for
Healthy people with no ongoing medical needs who are confident they'll have other coverage soon.
Avoid if
You have any pre-existing conditions, take regular prescriptions, or might actually need to use your insurance.
Watch out for
Coverage limits, exclusions, and state restrictions—short-term plans are banned or restricted in many states.
Typical cost
Less than ACA plans—often $100-300/month—but with much less coverage. Doesn't cover pre-existing conditions.
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COBRA
Continuation of your employer plan after you leave. You pay the full premium (employee + employer portion) plus 2% admin fee.
Best for
People mid-treatment who need specific doctor/hospital continuity, those who've already hit their deductible, or anyone needing just 1-2 months of bridge coverage.
Avoid if
You can get comparable ACA coverage for less. With reduced ACA subsidies in 2026, the gap has narrowed—run the actual numbers.
Watch out for
The sticker shock. You're now paying the full premium your employer used to subsidize.
Typical cost
Often $500-2,000/month. Whatever your employer was paying on your behalf, you now pay too. May be more competitive with ACA in 2026.
Spouse or Parent's Plan
Getting covered through someone else's employer plan. Losing your own coverage is a qualifying event that lets you join outside open enrollment.
Best for
Anyone who has this option available. Often the simplest solution.
Avoid if
Adding you makes the total cost higher than getting your own ACA plan.
Watch out for
Some employer plans charge significant premiums for spouse coverage. Compare before assuming it's the best deal.
Typical cost
Varies by employer plan. Contact their HR for the cost of adding you.
Medicaid
Government health coverage for people with low income. Generally if your income is under ~138% of the federal poverty level in expansion states.
Best for
Anyone who qualifies. If your income is low (especially temporarily due to job loss), check eligibility.
Avoid if
You don't qualify (income too high).
Watch out for
Eligibility varies significantly by state. Some states expanded Medicaid, others didn't.
Typical cost
Free or very low cost.
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COBRA vs ACA Calculator
Should you keep your employer coverage or switch to the ACA marketplace? Get a personalized estimate in 30 seconds.
Your projected income for this year, not last year's
Check your COBRA election notice for the exact amount
Not sure about your COBRA cost? Check your COBRA election notice from your employer, or call your former HR department.
Check Your ACA Options
Use the official Healthcare.gov estimator to see what subsidies you qualify for. That number will anchor every other decision.
Estimate Your CostsCommon Mistakes to Avoid
Electing COBRA immediately
You have 60 days, and it's retroactive. Use that time to compare ACA options. Many people pay for COBRA out of panic when cheaper alternatives exist.
Overestimating your income for ACA subsidies
If you're newly unemployed or starting freelance, your income this year might be much lower than last year. Subsidies are based on this year's projection. Don't accidentally disqualify yourself from help.
Buying short-term plans with pre-existing conditions
Short-term plans are cheaper because they exclude a lot. If you have any ongoing health needs, these plans won't cover them. Also check if your state even allows them.
Ignoring state-level rules
The federal penalty for being uninsured is $0. But California, Massachusetts, New Jersey, Rhode Island, and DC still have state penalties. Some states also restrict short-term plan availability.
Assuming employer coverage is always better
Sometimes it is. Sometimes ACA plans with subsidies are cheaper and just as good. Run the actual numbers.
Quick Decision Guide
| Your Situation | Recommended Path |
|---|---|
| Just lost job, generally healthy | ACA Marketplace (use COBRA as backup) |
| Just lost job, mid-treatment | Consider COBRA for continuity |
| Lost job, spouse has coverage | Spouse's plan (compare costs first) |
| Considering remote job without benefits | Do the math with ACA costs included |
| Freelance/self-employed, variable income | ACA via Stride Health |
| Freelance/self-employed, stable higher income | ACA via eHealth (compare more options) |
| Very low income | Check Medicaid eligibility |
| Just need 2-3 months, totally healthy | Short-term plan (if available) or COBRA safety net |
State Rules: What Varies by Location
Health insurance rules aren't uniform across the country
States with Individual Mandate Penalties
These states have their own penalties for being uninsured (the federal penalty is $0):
If you live in these states, factor the penalty into your "go uninsured" math—it rarely makes sense.
States Where Short-Term Plans Are Banned or Unavailable
Short-term health insurance is not available in these states:
If you're in one of these states, ACA plans or COBRA are your main options for coverage gaps.
Note: Short-term plan rules change frequently. Check current availability in your state before purchasing.
States with Their Own ACA Marketplaces
Most states use Healthcare.gov, but these states run their own marketplaces (enrollment deadlines may differ):
If you're in one of these states, go to your state marketplace instead of Healthcare.gov.
Frequently Asked Questions
You have 60 days to elect COBRA coverage (which is retroactive) and 60 days for ACA Special Enrollment after losing employer coverage. Don't wait until the last day, but you have time to make a thoughtful decision.
Not on ACA Marketplace plans or COBRA—they must accept you regardless of health history. However, short-term health plans and health sharing ministries can and do exclude pre-existing conditions.
For ACA plans, you estimate. If you earn more than expected, you'll pay back some subsidy at tax time. If you earn less, you'll get more back. Stride Health is good at helping freelancers with these estimates.
More often in 2026 than before. With reduced ACA subsidies, the cost gap between COBRA and marketplace plans has narrowed. COBRA still makes sense for mid-treatment continuity, hitting your deductible, or needing specific doctors. But always run the numbers—ACA may still be cheaper depending on your income.
The federal penalty is $0 (eliminated in 2019). A few states (CA, MA, NJ, RI, DC) still have state-level penalties. The bigger risk is financial—one serious medical event without coverage can be devastating.
Use the COBRA safety net. Don't elect it, but know it's there. If you get a new job quickly, you'll have coverage through them. If something happens in between, elect COBRA retroactively.
Yes. Losing COBRA coverage (including choosing to stop paying) is a qualifying life event that triggers an ACA Special Enrollment Period. Plan the transition timing carefully to avoid gaps.
Now, Back to the Job Search
Health insurance figured out? Find remote jobs that match your skills and lifestyle.