Retiring before 65 and need to get to Medicare
You are leaving work between 55 and 64, and your employer plan ends with it. I help you cover the years until Medicare without overpaying or gambling on the wrong plan.
Free. Never a fee. 7 days a week, 8 a.m.–10 p.m. ET.
Why the years before Medicare cost so much
Health insurance is priced on age. From 55 to 64 you are at the top of the scale, and the employer who paid most of your premium is gone. For most people, these are the most expensive coverage years of their life.
Many early retirees assume they will pay full price. Often they will not. It is the first thing I check.
The credit is based on your income in retirement
The Marketplace tax credit looks at the income you expect in the year you are covered, not your last working year. Many people retire into a lower income. Pension payments, part-time work, interest and dividends, and taxable withdrawals all count.
For 2026 coverage, the credit stops above 400% of the federal poverty level: $62,600 for one person, $84,600 for a couple. Above that line a Marketplace plan is full price. The enhanced credits from the pandemic years expired December 31, 2025, and Congress did not extend them. Source: KFF and the 2025 HHS poverty guidelines.
The measure is modified adjusted gross income. We work out where you land before you pick anything.
Three ways to bridge to Medicare
I run all three for you.
MARKETPLACE
A Marketplace plan with a credit
If your retirement income is under the cap, you likely qualify for a credit that lowers your premium every month. I check the exact amount before you pick anything. Losing employer coverage is a qualifying life event, so you can enroll outside open enrollment. No health questions.
COBRA
COBRA as a short bridge
You keep your employer plan, typically for up to 18 months, but you pay the full premium plus up to a 2% admin fee (federal COBRA rule). That number is often a shock. It can still make sense if you are mid-treatment or have already met a large deductible.
PRIVATE
A private plan if you are healthy
Applications year-round, priced on your health as well as age and ZIP. For a healthy early retiree above the income cap, one can cost less. But a carrier can decline you, rate you up, or exclude a condition. Not ACA coverage, and not guaranteed issue.
Before you pay for COBRA, see the real math. The math is laid out in COBRA alternatives, with the real numbers on SmartHealthMatch, the free matching service I built. Bring your COBRA election letter to our call and we will price it against the other two doors.
When each option wins
I place both kinds of plans, so you see both prices from one person, on one call.
When the Marketplace wins
- You have real medical history, ongoing prescriptions, or a surgery on the calendar.
- Your retirement income is under the cap and you qualify for a credit.
- You want a plan that cannot decline you or exclude a condition.
When a private plan wins
- You are healthy and your income is above the cap, so the Marketplace is full price.
- You want to apply now rather than wait for open enrollment.
- You have seen the private quote next to the Marketplace price and understand it is underwritten and not ACA coverage.
I will tell you which one it is, even when it earns me less.
Couples, and the handoff to Medicare
Most couples do not turn 65 in the same year. When one spouse moves to Medicare, the other still needs a plan, and the credit math changes because only one person is left on the Marketplace. I map both birthdays on one page so nothing lapses and nobody pays twice.
Medicare is a separate decision, and I do not sell Medicare plans. When you reach 65, I will point you to the right resource for it and help you end your current plan cleanly the month Medicare starts. I stay available for a spouse who still needs coverage before 65.
Open enrollment for 2027 coverage runs November 1, 2026 to January 15, 2027. Enroll by December 15 for a January 1 start. Source: CMS. Losing employer coverage at any other time of year opens a special enrollment period.
Two longer reads: health insurance for couples in their 50s and early retiree health insurance in Florida.
How working with me goes
A real conversation. Your retirement date, your income for the year, who needs coverage, your doctors and prescriptions, and when each of you turns 65. About 15 to 20 minutes by phone.
I run the numbers both ways. The Marketplace with any credit you qualify for, the true cost of COBRA, and, if you are healthy, a private quote. Side by side.
You decide, I enroll you. I handle the application and stay your contact until Medicare, through every renewal and any change in income.
Questions early retirees ask me
I have not retired yet. When should I call?
Two or three months before your last day is ideal. Losing employer coverage opens a special enrollment window, but it does not stay open forever. If you are already past your last day, call today.
Do my retirement withdrawals count as income?
It depends on the account and how you take the money. The credit uses modified adjusted gross income for the year you are covered. We walk through it together, and you confirm the details with your tax professional.
Is COBRA ever the right answer?
Sometimes. If you are mid-treatment or have already met a large deductible this year, keeping the same plan for a few months can be worth the full premium. We do the math.
Can I get a private plan with a health condition?
Maybe not, and I will not push you toward one. A carrier can decline, rate up, or exclude a condition. With real medical history, the Marketplace is the right door.
Do you charge a fee?
No. Carriers pay me a commission. There is never a fee to you for my time, my quotes, or my help after you enroll.
Get to 65 without a gap
Call me directly or book a time. Seven days a week, 8 a.m. to 10 p.m. ET.
Outside my 17 states? SmartHealthMatch, the free matching service I built, connects you with a licensed advisor in 48 states.