The wild west of healthcare
a guide to picking coverage in the lawless land of self-employment
Healthcare season is officially open and if you’re self-employed, this is your annual window to get covered.
Between now and January 15, you can sign up for health insurance through the Marketplace (HealthCare.gov) or a private plan.
If you enroll by December 15, your coverage starts January 1. Miss that, and you’re riding uninsured till next year.
The mission today: cross this terrain without getting hustled by confusing options or panic-buying the first plan you see.
Step 1: Marketplace or Private Plans
Think of healthcare like a spectrum. The Marketplace gives you affordable, no-frills coverage that adjusts to your income. Private insurance costs more but gives you more control over your doctors and coverage details.
The most common starting point is the public marketplace at Healthcare.gov. That is where most self-employed people end up because pricing adjusts to your income and the plans are standardized. You will see Bronze, Silver, and Gold plans there. Silver is usually the smart default for freelancers because it balances cost and coverage without feeling bare-bones or luxe.
You can also buy private insurance directly from companies like Oscar, Blue Cross Blue Shield, Kaiser, and Aetna. These are not offered through the marketplace and usually cost more, but they are helpful if you want a specific doctor or a concierge-style experience. Platforms like Stride Health help you compare plans.
There are also alternative private options like Solo Health Collective, which is built specifically for solo business owners. It is not an ACA (public) marketplace plan, so you will not get subsidies (government discounts), but it can be worthwhile if you have consistent income, prefer a more modern experience, and do not need marketplace tax credits.
💰 What It’ll Cost You
Marketplace (ACA, public plan): $350–$750/month
Private Plans: $400–$800/month
COBRA: $700–$1,200+/month (short-term bridge only)
Step 2: Plan Types
Regardless of what you choose between public and private, you’ll need to select a plan type. Confusing I know. Here’s a quick breakdown. Most freelancers opt for the PPO or EPO.
PPO (Preferred Provider Organization)
~$500–$750/month
See specialists without referrals, out-of-network coverage
Great for freelancers who travel or want maximum freedom.
EPO (Exclusive Provider Organization)
~$350–$550/month
No out-of-network coverage (except emergencies). Usually no referrals required
Solid choice if you stay local and want good value.
HMO (Health Maintenance Organization)
~$250–$450/month
Must stay in network. Referrals required for specialists
Typically lowest-cost. Works if you’re healthy, rarely see specialists, and don’t mind one network.
POS (Point of Service)
~$400–$600/month
Hybrid between HMO and PPO. Requires referrals
Fine in theory, rarely worth it in practice for freelancers.
💳 Step 3: HSA — The Freelancer’s Secret Weapon
If you qualify for a High Deductible Health Plan (HDHP), you can open a Health Savings Account (HSA): basically a tax-free emergency fund for medical costs.
Here’s why HSAs are gold for freelancers:
Triple tax advantage: Contributions are tax-deductible, your money grows tax-free, and withdrawals for medical expenses aren’t taxed.
Rolls over forever: Unused HSA money stays with you even if you don’t use it.
It can double as a retirement tool: After age 65, you can use HSA funds for anything (not just healthcare). You’ll just pay income tax, similar to a 401(k).
When you shop on HealthCare.gov, HSA-eligible plans are clearly labeled. Look for “HSA Eligible” in the plan name or description. For extra clarity, you can also use this quick tool from Fidelity to confirm your eligibility: 👉 Check if you qualify for an HSA.
Pro tip: Treat your HSA card like a long-term health fund, not a swipe-for-every-co-pay card. The less you touch it now, the more it compounds later.
📊 How to Budget for Healthcare
If you’re earning $100K/year, set aside 5–10% of your income for premiums + medical costs:
That’s roughly $400–$800/month
Add another $1K–$2K/year for out-of-pocket expenses
💡 Pro tip: Automate this into a “Health” sub-account in your high-yield savings. When your income fluctuates, your coverage won’t.
🔗 Freelancer-Friendly Tools
HealthCare.gov — official marketplace
Stride Health — comparison tool for freelancers
SoloHealthCollective - private plans for for freelancers (must have an EIN)
Oscar - private plans for freelancers
Policygenius — compare private plans
KFF Subsidy Calculator — estimate your monthly cost for public (marketplace) plans
💬 The Takeaway
Healthcare doesn’t have to be chaotic. It just requires one month of adulting each year.
Set aside your budget, compare plans, and make your future self proud.
Freelancers deserve coverage that works as hard as they do.
Hope it helps! Don’t forget to comment any other freelance finance struggles so we can cover them in a future post.
xo,
MHN
Disclaimer:
The information provided in this post is for educational and informational purposes only and should not be taken as medical, tax, or financial advice. Health insurance and tax situations vary, so please do your own research and consult a qualified professional before making decisions about your healthcare coverage or HSA eligibility. Mary & Pip does not provide medical services or act as a licensed insurance broker.