Planning your transition

Turning 65? Start before the mail piles up.

A little preparation can help you avoid missed deadlines, unnecessary penalties, and rushed coverage decisions.

Your Medicare starting checklist

Your timeline may differ if you are still working or covered through an employer. These steps help organize the conversation.

Review my timeline
1

Know your enrollment window

Your Initial Enrollment Period generally spans seven months: three months before your 65th-birthday month, the birthday month, and three months after.

2

Review current coverage

If you or your spouse are still working, find out how employer coverage coordinates with Medicare before making changes.

3

List doctors and prescriptions

These details matter when comparing provider access and prescription coverage.

4

Compare the full cost

Look beyond premiums to deductibles, copays, coinsurance, networks, and expected annual expenses.

Questions worth asking

Bring these to your Medicare conversation.

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Am I enrolling at the right time?

Employment, employer size, Social Security status, and existing coverage can affect the answer.

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Which doctors and hospitals matter?

Provider access can differ substantially between Original Medicare and network-based plans.

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What level of predictability do I want?

Consider both monthly premiums and the costs you may pay when receiving care.

Your Medicare timeline can start with one clear conversation.

Talk with Will