When executives need their own coverage
- Leaving a company, by choice or in a change of control.
- Retiring before 65, years before Medicare starts.
- Moving to board seats, advisory or consulting work, which is usually self-employment income with no employer plan.
- Starting or buying a company, before a group plan is in place.
Losing employer coverage opens a 60-day Special Enrollment Period for an individual plan, and you also have 60 days to elect COBRA.
COBRA, severance and individual plans
COBRA usually lasts 18 months and keeps your current plan and network. It is often the right bridge during active treatment or when you have met most of the year's deductible. It is also expensive: you pay the full premium plus up to 2%. Some separation agreements pay or reimburse COBRA for a period, so check yours.
Individual plans are guaranteed issue and cover pre-existing conditions. For 2027 the full-price benchmark Silver premium averages about $2,457/month for a couple aged 55 and $2,990/month for a couple aged 60 (national averages based on KFF's $704 benchmark for a 40-year-old). Broad PPO plans and Gold coverage cost more, and premiums vary a lot by county.
Retiring before Medicare
Early retirees are the one group of high earners who can control their subsidy. The 2027 credit is based on modified AGI, so a year of living on cash savings, Roth contributions or taxable account basis can keep income at or below 400% of the poverty level: $63,840 for one person or $86,560 for a couple.
Medicare starts at 65. Plan the handoff so individual coverage ends the day before Medicare begins, and enroll in Medicare on time to avoid late penalties.
Board and advisory income
Director fees and consulting income are usually self-employment income. With net self-employment earnings you can take the self-employed health insurance deduction for yourself, a spouse and dependents, as long as you are not eligible for a subsidized employer plan (including a spouse's) that month. Pair it with an HSA-eligible plan to deduct up to $9,000 (family) of HSA contributions for 2027.
What high-earning households should prioritize
- Access to top hospitals. Confirm the academic or specialty centers you would want for serious care are in network.
- Out-of-pocket ceiling. A predictable worst-case year matters more than a small premium difference.
- Coverage across homes. If you split time between states, check how each plan handles care away from home.
- Prescription formulary. Check every medication, tier and prior-authorization rule.
- Concierge or direct primary care can sit alongside insurance; it does not replace major medical coverage.
Frequently Asked Questions
Sources: IRS Rev. Proc. 2026-26 (2027 premium tax credit table) and Rev. Proc. 2026-24 (2027 HSA limits); 2026 HHS poverty guidelines; KFF, 2027 average benchmark premiums. Premium figures are national averages for planning, not quotes. Tax rules depend on your situation; confirm with your tax advisor.