For most people, Medicare arrives at the same time as several other big financial decisions: retirement, Social Security, portfolio withdrawals, tax planning, and the transition away from employer benefits.

That is why we view Medicare as part of the retirement plan—not a separate insurance decision.

You do not need to become a Medicare expert. But before age 65, you should understand the major choices, the deadlines, and the places where a seemingly small decision can create an expensive surprise.

A couple retires at the end of 2025. Their income falls, but their 2026 Medicare premiums still reflect the salaries they earned in 2024. Their retirement budget includes an extra charge for being high earners, even though their working years are behind them.

This can happen because Medicare generally looks back two years when determining income-related surcharges. Retirement may give them a way to ask Social Security to use more recent income information. For a household paying these charges, that review belongs on the retirement checklist.