I map private PPO and ACA coverage around your income rhythm, work style, doctors, and timing. Most freelancers enrolled in under 30 minutes.
A coverage blueprint you can count on.
Licensed in 43 states + DC, working for you.
Plans matched to your health, income, and timing.
Clear guidance and reliable support every step.
I start with your doctors, prescriptions, health needs, budget, income, and timing. Then I compare private PPO and ACA marketplace options and help match you with the coverage that best fits your specific situation.
Most freelancers default to whatever ACA plan was cheapest on healthcare.gov — which is fine if it's the right answer, but it usually isn't once your income stabilizes. Here's how the math typically breaks down.
Usually right once your income stabilizes. Most full-time freelancers earn above ACA subsidy thresholds, which makes full-price marketplace plans expensive. Private PPOs are typically 20–50% cheaper for healthy individuals, with much wider networks. If you're past your first year and reasonably healthy, this is usually the move.
Better for new freelancers or lower-income years. First year of freelancing, slow client cycles, or genuinely lower-income brackets unlock real ACA subsidies. Plus guaranteed coverage with no medical underwriting — which matters if you have ongoing prescriptions or any pre-existing condition.
The tax-efficient layer. Both private and ACA offer HSA-compatible high-deductible plans. For freelancers with steady income, HSA contributions reduce your taxable income now and the funds compound tax-free forever for medical use. Whether this is your best move depends on bracket and expected utilization — I'll run the numbers.
1. ACA subsidies use projected income, not last year's 1099 total. Freelancers ramping up or down often skip ACA because they project from their best year and assume they don't qualify. Project honestly based on signed contracts plus realistic pipeline, not best-case. ACA reconciles at tax time either way — under-project and you pay back some subsidy; over-project and you get a refund. The bigger mistake is overestimating and missing subsidies entirely.
2. Self-employed premiums are deductible above-the-line. Health insurance premiums for self-employed people come off the top on Schedule 1 (line 17), reducing your AGI before the standard deduction. For freelancers in the 24% federal bracket, that's effectively a 24% discount on every premium dollar — and it stacks with state tax savings. The real after-tax cost of a $500/month plan is closer to $350 once the deduction is factored in. Comparing pre-tax dollars to post-tax dollars makes plans look much worse than they really are.
3. If you're freelancing through an LLC or S-corp, premium handling gets nuanced. There are specific rules about how premiums flow from the business to your personal return — and the right setup depends on whether you're a sole prop, single-member LLC, or S-corp owner-employee. I work with your CPA to coordinate. The short version: most freelancers should pay premiums personally and deduct on Schedule 1, but S-corp owners have a different path that's worth getting right.
Quick form or call. Expected income, state, family situation, any health considerations. That's it.
Side-by-side numbers including the tax angle, so you're comparing real after-tax costs — not sticker prices.
We enroll on the call. Most freelancers are covered the same day, then I'm here when your situation changes next year.
I freelance design for ad agencies — mostly remote, sometimes traveling for shoots. My old plan was a marketplace EPO that only worked in one state, which was a problem the first time I needed care while at a client site. Christian moved me to a private PPO that's nearly $200 a month cheaper and works anywhere I happen to be working from. He also walked me through HSA contributions for the year. Twenty-minute call.
No. If you left a job with employer coverage, losing it triggers a Special Enrollment Period for ACA (60 days from when employer coverage ends), and private PPO plans accept new enrollments year-round regardless. Don't wait — your old plan ends when your employment ends, and the gap is the part that hurts.
Project conservatively based on signed contracts plus realistic pipeline, not best-case scenarios or last year's 1099 total. ACA reconciles at tax time — if you under-project and earn more, you pay back some subsidy; if you over-project, you get a refund. The bigger mistake most freelancers make is overestimating and missing subsidies they actually qualified for.
Depends on your situation. HSAs are the most tax-advantaged accounts in the US — triple tax benefit (deductible going in, growth tax-free, withdrawals tax-free for qualified medical). For high-earning, low-utilization freelancers, the math is compelling. For freelancers with ongoing prescriptions or expected medical needs, the high deductible can sting. I run both scenarios with your real numbers.
Some are useful, some are intermediaries that point you to the same ACA marketplace you can shop directly. The advantage of working with an independent broker is unbiased advice — I make the same income regardless of which carrier you pick, so my only job is to find your best fit. Worth comparing those platforms to what I quote, and I'll show you honestly when they win.
Fifteen minutes, real numbers, and an honest comparison of every option you qualify for. Then you can get back to the work that actually pays.
Tell me a bit about your situation — I'll run the numbers and call you back.
I'll be in touch shortly. Need to talk right now? Call (941) 241-0210.
