I map private PPO and ACA coverage around contract income, multi-state work, doctors, and the tax angle most contractors miss. Most clients 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.
Whether you've been on a 1099 for years or your company just reclassified you last week, the answer isn't always the same. Here's how the math typically works out.
Usually the right call for established 1099s. Most full-time contractors earn above ACA subsidy thresholds, which makes full-price marketplace plans expensive. Private PPOs are typically 20–50% cheaper for healthy individuals with much broader networks. If your contract income is steady and above $60K, this is usually the move.
Better for new 1099s, between contracts, or pre-existing conditions. Subsidies are based on projected income — so a transition year, an unexpected gap, or a deliberately slower stretch can unlock real savings. Plus guaranteed coverage with no medical underwriting if you have pre-existing conditions or ongoing prescriptions.
The tax stacker for higher-income contractors. Self-employed 1099s can stack HSA contributions (triple tax-advantaged) on top of the Schedule 1 premium deduction. For contractors in the 24%+ federal bracket, the after-tax math is often hard to beat. I'll model both scenarios with your real numbers.
1. If your employer just moved you W-2 to 1099, you have a 60-day window. Reclassification ends your employer coverage on a specific date. That triggers a Special Enrollment Period for ACA — 60 days to enroll, no waiting for open enrollment. Private PPOs accept new applications year-round regardless. Don't wait for the COBRA paperwork to arrive; the cheapest options are usually elsewhere.
2. Self-employment tax is painful, but the premium deduction softens it. As a 1099 you pay an extra ~15.3% self-employment tax on top of regular income tax (both halves of FICA). It stings. But your health insurance premiums are deductible above-the-line on Schedule 1 (line 17), reducing your AGI before the standard deduction even applies. For contractors in the 24–32% federal brackets, that takes 24–32 cents off every premium dollar — and the after-tax cost of your plan is very different from the sticker price.
3. Long-term single-client 1099s have a different planning picture. If you've been with one client for years on a 1099 basis, your situation is different from a contractor juggling six clients. Income is steadier, planning is easier, and the math sometimes favors S-corp election (which can save on SE tax) — but that changes how health premiums flow through your return. Worth coordinating with a CPA before locking in plan choices for the year.
Annual income, state, family situation, business structure if you have one. That's most of what I need.
Private PPO, ACA, and HSA scenarios — all priced on real after-tax cost, not sticker price.
Same-day enrollment. Coverage starts on schedule, and I'm here when your contract or income changes.
My company moved everyone in my role from W-2 to 1099 last year — basically the same work, just no benefits. I figured I'd just COBRA my old plan while I sorted everything out. Christian showed me a private PPO for less than half my COBRA quote, walked me through what I'd save deducting premiums on my taxes, and we had it set up before COBRA even kicked in. He also flagged that I should talk to a CPA about S-corp election. Saved me real money on day one.
Probably not for long. When your employment status changes to 1099, your employer-sponsored coverage typically ends on a specific date (often the end of the month). You have 60 days from that date to enroll in an ACA plan, and private PPOs are available year-round. Don't wait — gaps in coverage are how preventable problems turn into expensive ones.
Probably not. COBRA is the option HR hands you, but it's almost always more expensive than a private PPO or subsidized ACA plan. I'll quote your COBRA cost against your real alternatives so you can see the difference. Most of my contractor clients skip COBRA entirely once they see the math.
Yes, fully — above-the-line on Schedule 1 of your federal return (line 17). That reduces your AGI before the standard deduction, which is the most valuable kind of deduction. For higher-income contractors, this is often 24–32% off the real cost of your plan. I factor the tax angle into the comparison so you're not comparing pre-tax to post-tax dollars.
They're related but separable. Buying health insurance doesn't require an LLC or S-corp — you can deduct premiums as a sole proprietor on Schedule 1. But S-corp election changes how you handle self-employment tax and how premiums flow through your return. Worth coordinating with a CPA before year-end. I work with your tax pro to get the structure right alongside the insurance.
Fifteen-minute call, real numbers with the tax angle built in, and a plan that fits how contract work actually pays. Most contractors covered same day.
Tell me a bit about your contract picture — I'll run the numbers with the tax angle and call you back.
I'll be in touch shortly. Need to talk right now? Call (941) 241-0210.
