How to Get Health Insurance as a Freelancer: My $7,200/Year Reality
The single scariest thing about going freelance wasn’t finding clients or managing taxes. It was losing health insurance. My employer plan cost me $180/month (they covered the rest). As a freelancer, the same level of coverage would cost $600-700/month. That’s $5,000-6,000 more per year, paid by me.
I went 4 months without insurance after leaving my job. Stupid, I know. One broken arm or appendicitis would have cost me $20,000-50,000. I got lucky. You shouldn’t rely on luck.
Here’s everything I’ve learned about freelance health insurance — the options, the costs, and the tax deduction that makes it slightly less painful.
Your Options
1. ACA Marketplace Plans (What I Use)
The Affordable Care Act marketplace (healthcare.gov) is where most freelancers get insurance. Open enrollment is November 1 - January 15. If you recently left a job, you have a 60-day special enrollment period.
How it works: You shop for plans on the marketplace based on your location, age, and estimated income. Plans are organized by metal tier:
| Tier | Monthly Premium (avg, single 35yo) | Deductible | Best For |
|---|---|---|---|
| Bronze | $300-400 | $7,000-8,000 | Healthy, rarely use healthcare |
| Silver | $450-650 | $4,000-6,000 | Moderate healthcare needs |
| Gold | $600-800 | $1,000-2,500 | Regular healthcare use |
| Platinum | $700-1,000 | $0-500 | Frequent healthcare needs |
What I have: A Silver plan at $600/month ($7,200/year) with a $5,000 deductible. It covers:
- Preventive care (annual checkup, vaccines): free
- Doctor visits: $40 copay after deductible
- Specialist visits: $80 copay after deductible
- Generic prescriptions: $15
- ER: $500 copay after deductible
- Max out-of-pocket: $9,100/year
Is $600/month a lot? Yes. Is it worth it? Also yes. My friend (also a freelancer) broke his wrist snowboarding. Without insurance, the ER visit + X-ray + cast + follow-up would have been $12,000+. With a Silver plan, he paid about $2,500 (deductible + copays).
Subsidies Can Dramatically Reduce Your Cost
If your Modified Adjusted Gross Income (MAGI) is below 400% of the federal poverty level (~$60,240 for a single person in 2026), you qualify for premium tax credits that reduce your monthly payment.
Example subsidy scenarios (single, age 35):
| Income | Approximate Premium After Subsidies |
|---|---|
| $30,000 | $50-150/month |
| $40,000 | $150-300/month |
| $50,000 | $250-450/month |
| $60,000 | $400-600/month |
| $70,000+ | Full price (no subsidy) |
Strategic consideration for freelancers: Your subsidy is based on your estimated income for the year. If you’re having a slow year, your subsidies increase. If you’re having a great year, you may owe back some subsidies at tax time. Estimate conservatively and be prepared for true-up at filing.
Another strategic move: Maximizing pre-tax retirement contributions (SEP IRA, Solo 401(k)) reduces your MAGI, which can increase your marketplace subsidies. Contributing $10,000 to a SEP IRA could boost your monthly subsidy by $50-100. Your accountant can model this.
2. COBRA (Temporary Bridge)
When you leave employer coverage, COBRA lets you continue the same plan for up to 18 months. The catch: you pay the FULL premium (your share + your employer’s share + a 2% admin fee).
My employer plan that cost me $180/month was actually $680/month total (employer paid $500). COBRA would have cost me $694/month ($680 × 1.02).
When COBRA makes sense:
- You’re mid-treatment and don’t want to switch doctors/networks
- You’re leaving mid-year and want to bridge to the next open enrollment
- You have a high-deductible plan and already met the deductible this year
When to skip COBRA:
- A marketplace plan is cheaper (often the case)
- You’re healthy and a Bronze plan would save money
- You qualify for marketplace subsidies
3. Spouse’s Employer Plan
If your spouse has employer coverage, joining their plan is usually the cheapest option. Adding a spouse costs $200-400/month on average, and the employer often subsidizes a portion.
This was the plan I eventually landed on when my partner got a job with good benefits. My insurance cost dropped from $600/month to $250/month on their employer plan. Life-changing.
4. Health Insurance Marketplaces (Private)
Companies like eHealth, Oscar, and Sidecar Health offer plans outside the ACA marketplace. These sometimes have different networks or structures. I briefly explored these but found marketplace plans to be more transparent and better regulated.
5. Health Sharing Ministries
These aren’t insurance — they’re member organizations where people share medical costs. Monthly “shares” are typically $200-400/month. Popular options include Medishare, CHM, and Liberty HealthShare.
Caution: Health sharing ministries aren’t regulated like insurance. They can deny claims based on lifestyle choices, pre-existing conditions, or other criteria that actual insurance can’t. They’re also not guaranteed to pay. I personally wouldn’t rely on one as primary coverage, but some freelancers use them to save money.
6. Short-Term Health Insurance
Cheap ($100-200/month) but limited. Short-term plans don’t cover pre-existing conditions, don’t meet ACA requirements, and have low coverage limits. They’re a stopgap, not a solution.
7. Freelancers Union
If you’re a member of the Freelancers Union (free to join), they offer group plans in some states. Worth checking if available in your area.
The Tax Deduction That Makes It Less Painful
Self-employed health insurance is 100% deductible as an above-the-line deduction. This is one of the most valuable deductions available to freelancers.
On my $7,200/year premium at a ~28% effective tax rate: $7,200 × 0.28 = $2,016 in tax savings
This effectively reduces my insurance cost from $600/month to about $432/month after tax savings. Still not cheap, but substantially less painful.
What qualifies:
- Health insurance premiums for you, your spouse, and dependents
- Dental insurance premiums
- Vision insurance premiums
- Long-term care insurance premiums (age-limited)
What doesn’t qualify:
- Premiums for months where you were eligible for employer coverage (even if you didn’t enroll)
- Premiums that exceed your net self-employment income
How to claim it: Line 17 on Schedule 1 (Form 1040). It’s above-the-line, so it reduces your AGI even if you don’t itemize. Your accountant handles this, or TurboTax/FreeTaxUSA will walk you through it.
Don’t miss this. I know freelancers who paid for their own insurance for years without claiming this deduction. One friend missed $18,000 in deductions over 3 years. That’s roughly $5,000 in overpaid taxes.
How to Choose a Plan
If you’re healthy and rarely see doctors: Bronze plan. Low premium, high deductible. You’re basically paying for catastrophic coverage. Monthly cost: $300-400.
If you have moderate healthcare needs: Silver plan. Middle ground on premium and deductible. This is the most common choice for freelancers and what I use. Monthly cost: $450-650.
If you take medications or see specialists regularly: Gold plan. Higher premium but lower out-of-pocket costs. The math often works out better if you’re spending $200+/month on healthcare. Monthly cost: $600-800.
Key tip: Look at total annual cost (premiums + expected out-of-pocket), not just monthly premium. A Gold plan at $700/month with a $1,500 deductible might cost less annually than a Bronze plan at $350/month with an $8,000 deductible — IF you use healthcare regularly.
My Insurance Timeline
Months 1-4 of freelancing: Uninsured (stupid) Months 5-18: Bronze marketplace plan ($320/month). Healthy, rarely used it. Months 19-30: Upgraded to Silver ($550/month) after a health scare made me realize I needed better coverage. Months 31-36: Silver plan ($600/month after premium increase). Month 37-present: Spouse’s employer plan ($250/month). The dream.
Total spent on health insurance in 4 years: approximately $22,000. Tax deduction savings: approximately $6,000. Net cost: $16,000. Expensive, but cheaper than one hospital stay without insurance.
Dental and Vision
Marketplace plans don’t always include dental and vision. Standalone plans are available:
Dental: $25-50/month. Covers cleanings, X-rays, basic procedures. I have a standalone dental plan at $35/month.
Vision: $10-20/month. Covers annual exam and discounts on glasses/contacts. I skip vision insurance because an annual exam is $100 out of pocket and I don’t wear glasses. The math doesn’t favor the insurance for me.
The Bottom Line
Health insurance is expensive, non-optional, and tax-deductible. That’s the summary.
Get covered. Don’t go uninsured. Shop the marketplace during open enrollment. Claim the deduction. Factor $400-700/month into your freelance rate calculations.
And if you’re currently uninsured and reading this: healthcare.gov allows special enrollment within 60 days of losing other coverage, or during annual open enrollment (November 1 - January 15). If neither window applies, some states have extended enrollment periods. Check your state’s marketplace.
Your freelance career isn’t worth risking over one medical bill. Get covered today.