If you retire before 65, you have a planning problem most retirement advice ignores: how to cover the years between leaving work and starting Medicare. Those in-between years — often called the “bridge years” or “gap years” — are when health coverage is most expensive on the open market, income from Social Security typically hasn’t started, and one wrong move can derail a retirement plan.
This guide walks through the income, health insurance, and tax decisions that matter most during the bridge years, and how to build a plan that gets you to 65 without burning through your savings.

Quick answer: what are the bridge years?
The bridge years are the period between your last day of work and your first eligible day of Medicare (the month you turn 65 for most people). Some retirees plan for a 1–2 year bridge; others plan for 10 years or more. The bigger the bridge, the bigger the planning problem.
The two big problems
Two costs dominate the bridge years and need a real plan:
- Health insurance. No more employer coverage, and Medicare doesn’t start until 65. Premiums on the individual market for a 60-year-old can run $800–$1,500+ per month per person without subsidies.
- Income. Most retirees haven’t started Social Security yet, may not have access to a pension, and often shouldn’t be drawing from tax-deferred accounts at full speed yet (RMDs aren’t until 73). The cash has to come from somewhere — ideally from the most tax-efficient source.
Health coverage options before Medicare
ACA marketplace plans (healthcare.gov or your state exchange)
For most early retirees, the ACA marketplace is the default option. You’ll find Bronze, Silver, Gold, and Platinum plans, and you can apply during open enrollment or under a special enrollment period (losing employer coverage qualifies). Premium tax credits are based on your modified adjusted gross income (MAGI), not assets — meaning you can have substantial savings and still qualify for subsidies if your taxable income is low.
For early retirees living off cash, taxable account withdrawals (where most of the withdrawal is principal), and a small amount of dividends, MAGI can be surprisingly low. Many retirees in their early 60s qualify for sizable premium subsidies that they assumed only applied to lower-income households.
COBRA
COBRA lets you continue your employer’s plan after leaving, usually for 18 months. The catch: you pay the full premium yourself, including what your employer used to cover — often $1,500–$2,500+ per month for family coverage. COBRA is sometimes the right answer for short bridges (under 18 months) or when you’re mid-treatment and want to keep the same network. For longer bridges, the marketplace is usually cheaper.
Spouse’s employer plan
If your spouse is still working and has employer coverage, joining their plan may be the cleanest answer. Losing your own coverage typically counts as a qualifying event for mid-year enrollment.
Part-time work with benefits
Some retirees take a part-time job specifically because it includes health benefits. A bridge job that pays for coverage can pay for itself even at a modest hourly rate when you compare it to what marketplace premiums would cost.
Health-sharing ministries (proceed carefully)
Health-sharing arrangements are not insurance. They are membership organizations that share medical costs among members. They’re cheaper than ACA premiums but can deny claims, may not cover pre-existing conditions, and provide no legal guarantee that your bills will be paid. Suitable only for healthy retirees willing to absorb that risk.
How MAGI shapes your bridge-year plan
Premium tax credits on the ACA marketplace are tied to MAGI. The lower your MAGI, the more subsidy you get. A higher MAGI — from a Roth conversion, a large IRA withdrawal, or capital gains on a stock sale — can reduce or eliminate the subsidy entirely. For some retirees in the bridge years, an extra $10,000 of taxable income can cost $5,000–$8,000 in lost premium credits.
This creates a planning tension. The bridge years are the classic Roth-conversion window (low income, conversions taxed at low brackets), but big conversions can wipe out ACA subsidies. The right answer is usually a calibrated middle path: convert just enough to fill a target bracket without crossing the subsidy cliff.
Where bridge-year income should come from
There’s a rough hierarchy for funding the bridge years, from most to least tax-efficient:
- Cash and emergency savings. Already-taxed money, no tax impact when spent.
- Taxable brokerage account. Sells of long-held positions are usually long-term capital gains, often taxed at 0% or 15%. Cost basis is principal — only the gain is taxed.
- Roth IRA contributions. Original contributions can be withdrawn tax- and penalty-free at any age (earnings are different).
- Roth IRA conversions (5+ years old). Conversions you did 5+ years ago can be withdrawn penalty-free if you’re under 59½.
- Traditional IRA / 401(k). Fully taxable income. Best used in years where the marginal rate is low or where the alternative is much worse.
- Social Security. Often best to delay if possible — benefits grow ~8% per year after FRA up to age 70.
A common bridge-year strategy: live mostly off taxable accounts and Roth contributions, do measured Roth conversions up to a target tax bracket, and hold off on Social Security until later (often 70 if longevity is reasonable).
Don’t forget HSAs
If you have an HSA, the bridge years are an excellent time to use it — or to keep saving in it if you still have a high-deductible health plan. HSAs can pay for medical expenses tax-free at any age. After 65, the penalty for non-medical withdrawals disappears (you just pay income tax, like a traditional IRA). HSA dollars are some of the most flexible retirement money you can have.
Common bridge-year mistakes
- Underestimating health insurance costs. Marketplace premiums for two people in their early 60s can run $1,800–$3,500+ per month without subsidies.
- Doing a large Roth conversion that knocks out the ACA subsidy. The subsidy loss often exceeds the tax savings.
- Claiming Social Security at 62 just to fund the bridge. Often a permanent ~30% benefit reduction. Use other accounts first if possible.
- Ignoring state subsidies. Some states offer additional ACA subsidies on top of the federal premium tax credit.
- Forgetting Medicare enrollment. If you’re still on a marketplace plan at 65, you typically need to actively enroll in Medicare during your initial enrollment window. Missing it can mean lifetime Part B late penalties.
- Drawing pre-tax money first when Roth or taxable would be cheaper. Withdrawal order matters more in bridge years than almost any other time.
A simple bridge-year framework
- Estimate your annual spending for the bridge years (housing, food, transportation, plus a realistic health-insurance line item).
- Figure out where each year’s cash comes from — cash, taxable, Roth, traditional — in roughly the order above.
- Project your MAGI in each bridge year. This drives premium subsidies and IRMAA.
- Decide whether to do measured Roth conversions, taking ACA subsidy effects into account.
- Decide when Social Security starts — the longer you can wait, the larger the lifetime benefit.
- Plan your Medicare enrollment timing so it’s automatic when 65 arrives.
What to do next
If you’re heading into bridge years — or already in them — the highest-leverage step is sketching out your annual income sources and projected MAGI for each year up to 65. From there, the health insurance and Roth conversion decisions follow logically. For most early retirees, this is a planning area where running the numbers (or paying a fee-only advisor for a few hours) more than pays for itself.
Further Reading
- Health Coverage Before Medicare for Early Retirees
- Roth Conversions Explained
- Tax-Efficient Withdrawal Order in Retirement
- When to Claim Social Security: 62, FRA, or 70?
- Healthcare Costs in Retirement
- Medicare and HSAs
- How Much Do You Need to Retire?
This article is for general educational purposes only and does not constitute tax, financial, or insurance advice. Health insurance options, premium subsidies, and Medicare rules vary by state and individual circumstances — verify details with healthcare.gov, your state marketplace, or a licensed broker before making coverage decisions.


