Life events · Guide
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.
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.
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.
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.
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.
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.
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.
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.
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.
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