The five years before · Retirement Transition Trap™
Health coverage before Medicare
A reason a retirement date can quietly move back a year.
In short
Anyone retiring before Medicare eligibility has a coverage gap to fund. It is a reason retirement dates move, and it is often discovered later than it should be.
How it works
Employer coverage usually ends with employment. Medicare begins at a set age. If your retirement date is earlier than that age, the difference is a gap you have to bridge and pay for yourself.
The cost of bridging it can be one of the larger new expenses in the first phase of retirement, and it is easy to discover late.
It is connected to your income, which makes it a planning decision
Coverage bought on an individual basis can be income-sensitive. That links the coverage question directly to withdrawal order and to conversions: the income you choose to realize in a given year can change what coverage costs in that year.
So this is not simply an expense to budget for. It is one of the constraints that shapes how income is taken during the bridge years.
Why it moves retirement dates
When the bridge cost is priced properly for the first time, one of three things usually happens: the date moves later, the spending plan changes, or the income strategy for those years is rebuilt around the coverage question.
All three are manageable outcomes. What is not manageable is finding out in the month after the last paycheck.
This page explains a mechanism. It is not investment, tax or legal advice, and it deliberately quotes no thresholds, ages or rates. Those are set annually, and a page that named them would be out of date within a year.
Check where you stand
Ten questions, about two minutes
The readiness checklist covers this and nine other checkpoints, and tells you which you have already handled. No contact details required.
Where does this sit in your plan?
Fifteen minutes on the phone about your own situation, which is the part this page can’t tell you.