Life events · Guide

Turning 65: the money checklist.

Sixty-five comes with deadlines that don't announce themselves: enrollment windows, permanent penalties, and timing decisions worth six figures over a retirement. This is the sequence.

1

Mark the Medicare initial enrollment window

It runs seven months: the three months before your 65th-birthday month, that month, and the three after. The paperwork is easier at the start of the window than the end.

2

Understand the Part B late penalty before delaying

Enroll late without qualifying coverage and the premium rises 10% for each full 12-month period you waited, and the increase is permanent, not a one-time fee.

3

Check whether work coverage lets you wait

Coverage from an employer with 20 or more employees generally lets you delay Part B without penalty. COBRA and retiree plans usually don't count. Verify before assuming.

4

Pick Medigap or Medicare Advantage deliberately

The six months after Part B starts is the guaranteed-issue window for Medigap; apply later and insurers in most states can underwrite or decline you. The choice is harder to reverse than it looks.

5

Decide Social Security timing on math, not habit

Benefits can start anywhere from 62 to 70, and each year of delay past full retirement age adds roughly 8% for life. Health, spousal benefits, and other income all belong in the calculation.

6

Stop HSA contributions before Medicare begins

Medicare enrollment ends HSA eligibility, and Part A can apply retroactively up to six months. Contributions made after eligibility ends create tax problems worth avoiding.

7

Put required minimum distributions on the calendar

RMDs from traditional retirement accounts currently begin at age 73, and missing one carries a steep penalty. Knowing the number early helps plan the tax brackets in between.

8

Re-run the retirement budget with real premiums

Part B, Part D, and Medigap premiums are real line items, and Medicare doesn't cover most dental, vision, or long-term care. The budget should reflect what's actually covered.

Astra runs this checklist with you.

Every step above is a guided project inside Astra, with your real accounts and numbers.

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Educational information, not professional financial, legal, tax, or investment advice. Programs, limits, and windows vary by state and plan. Verify details for your situation.

Also in this series: Having a baby · Buying a home · Getting married · Losing a job · Starting a business · Caring for aging parents · Going through a divorce · Facing a medical crisis · Losing a loved one · Sending a kid to college · Inheriting money · Special needs planning · Relocating to a new state · Planning for early retirement