Planning ahead

Retiring before 65: how to bridge the gap to Medicare

Health insurance is the reason a lot of people work longer than they need to. It is a solvable problem, and the solution is mostly about how you manage income in the bridge years.

If you retire at 62, you have three years to cover before Medicare. For many households that gap is the single biggest obstacle to retiring at all — and it is far more manageable than it looks, provided you plan the income side deliberately.

Your options, honestly assessed

For most people retiring before 65 without a working spouse, the Marketplace is where the answer lives. What makes it work is that your income in retirement is often exactly the kind of income the subsidy structure is designed around.

  • A Marketplace plan with an advance premium tax credit — the primary route for most early retirees, and the one where planning pays
  • A spouse's employer plan, if one is still working — usually the simplest answer when it is available
  • COBRA from your former employer — familiar and unsubsidised, typically capped at 18 months
  • Retiree coverage from a former employer, if you are fortunate enough to have it offered
  • Short-term medical — a stopgap only, with real exclusions, and not eligible for the tax credit

The insight that changes the maths

The premium tax credit is based on your modified adjusted gross income for the year — not on your net worth, and not on what you have saved. A household with substantial retirement assets can have modest taxable income, and the credit follows the income.

That means how you fund your living expenses in the bridge years directly changes what you pay for health insurance. Which accounts you draw from, when you realize gains, and whether you convert to a Roth before or after 65 are health insurance decisions as well as tax decisions.

What counts as income, and what does not

Broadly, these are counted:

  • Taxable withdrawals from traditional IRAs and 401(k)s
  • Roth conversions in the year you convert
  • Realised capital gains, dividends and taxable interest
  • Pension payments and any wages or self-employment income
  • The taxable portion of Social Security, plus tax-exempt interest added back

Where the thresholds sit

Two thresholds matter in the bridge years. Below roughly 250% of the federal poverty level for your household size, cost-sharing reductions are available on Silver plans — which materially lowers your deductible and copays, not just your premium.

Above that, credits continue on a sliding scale, so there is no single cliff to fall off, but the amount tapers. The practical point is that a Roth conversion or a large realized gain in a bridge year can quietly cost you thousands in lost credits and lost cost-sharing reductions. That trade may still be worth making — but it should be a decision, not an accident.

Do not forget the rest of the picture

Medicare covers dental, vision and hearing barely or not at all, and neither does a Marketplace plan in the way people assume. If you have dental work you have been postponing until retirement, price standalone coverage before you retire rather than after.

It is also worth thinking about how the bridge ends. The transition to Medicare at 65 has its own deadlines, and your Marketplace plan does not roll into Medicare automatically. Plan that handoff about six months out.

A realistic sequence

  • Twelve months before retiring: estimate your bridge-year income under two or three drawdown strategies
  • Nine months before: price Marketplace plans in your county at each income level, and check the cost-sharing reduction threshold
  • Six months before: check your doctors and prescriptions against the plans you are considering
  • Three months before: confirm your Special Enrollment Period timing so coverage starts the day the old plan ends
  • Each autumn during the bridge: re-run the numbers, because plans, prices and your income all change
  • Six months before 65: start the Medicare conversation and plan the handoff

Coordinate, do not improvise

The health insurance decision and the drawdown decision are the same decision viewed from two angles, and they are usually made by two different people who never speak. Your tax professional owns the tax side. An insurance agent who understands the subsidy structure owns the coverage side.

Getting them to look at the same numbers once, before you retire, is worth more than any single plan choice you will make in those years.


The bottom line

Retiring before 65 is a solvable problem. Plan the income side, check the cost-sharing reduction threshold, and start about a year out. Sarah works with early retirees across Northern Utah on exactly this bridge — and she will tell you plainly if a spouse's plan or COBRA is the better answer.

Want to go through this with someone?

Sarah will go through your doctors, your prescriptions and your real numbers, and tell you plainly what she found. No cost, no pressure.

Book a call 435-292-8777Speak with a licensed insurance agent · TTY 711

Please note: CUPS Insurance is not affiliated with, endorsed by, or operating on behalf of HealthCare.gov, the Health Insurance Marketplace, or any federal or state government agency. Plan availability, premiums and advance premium tax credits are set by the carriers and the Marketplace. Estimates only. Figures on this page use published 2026 plan-year values and the details you enter. They are not a quote, an offer of coverage, or a determination of eligibility. Your final premium and any advance premium tax credit are confirmed at enrollment on HealthCare.gov or with the carrier.

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FAQ

Common questions

What does it cost to work with CUPS Insurance on Retiring before 65?

Nothing. Carriers pay a commission when a plan is issued, and that commission is already built into the plan price whether you use an agent or not.

Buying the same plan on your own does not make it cheaper — it just means nobody checked your doctors and prescriptions first, and nobody picks up the phone in March when something goes wrong.

Does CUPS Insurance offer every plan available for Retiring before 65?

No, and no agency does. We are independent, which means we compare across the carriers listed on this site rather than representing a single one — but that is not the same as offering every plan on the market.

We do not offer every plan available in your area. Currently we represent 8 organizations which offer 72 products in your area. Please contact Medicare.gov, 1-800-MEDICARE to get information on all of your options.

Who will actually be helping me?

Sarah Wood Rodriquez, licensed since 2009 — over 17 years — and licensed in Utah, Arizona, Idaho. NPN 14943086.

The person who answers the phone is the person who reviews your plan. There is no call center and no handing you between departments.

How do I get started with Retiring before 65?

Call Sarah, a licensed insurance agent, at 435-292-8777 (TTY 711) or book a call. The first conversation usually runs twenty to thirty minutes and there is nothing to sign.

Bring your prescription list and your doctors’ names — with those, the comparison can be a real one rather than a generic one.

What happens after I enroll?

She stays your agent. If a prescription moves tier, a doctor leaves the network, or a letter arrives that makes no sense, you call the same number and speak to the same person.

Every autumn your plan gets reviewed before Open Enrollment, because plans change even when your health does not. On Retiring before 65 that matters as much as the original enrollment.

Do we have to meet in person?

No. Most conversations happen by phone or video, which is faster for most people. If you would rather meet face to face, the office is at 3293 Harrison Blvd #213, Ogden — by appointment only, so call before you come.

Hours are 10:00 AM – 5:00 PM, Monday to Friday.

Can I do all of this in Spanish?

Yes. The whole site is available in Spanish and English, and appointments, paperwork and follow-up can be handled in Spanish from start to finish.

If you would rather talk in Spanish, say so when you call Sarah, a licensed insurance agent, at 435-292-8777 (TTY 711) and it is handled that way from the first conversation.

What happens to my personal information?

The calculators on this site run entirely in your browser — nothing you type is sent anywhere, including to us.

If you contact us, your details are used only to help with your coverage. We do not sell or share your information with third parties for marketing.

Grab a cup. Let's make insurance make sense.

A real conversation with a licensed agent who will check your doctors and prescriptions before you decide — and answer the phone all year after that.

Book a call with Sarah Call 435-292-8777 Speak with a licensed insurance agent · TTY 711

Office hours: 10:00 AM – 5:00 PM · Ogden, Utah · NPN 14943086