Retirement Timeline
A countdown of what to handle before you leave work — and what to check in the first month after. Download the graphic, or use the checklist below.
12 months out
- Map your first-year spending and big one-time costs
- Stress-test retiring into a bad market
- Verify Social Security and pension records
- Map your health coverage transition
- Check what you lose or vest when you leave
6 months out
- Build first-year cash reserves
- Check when HSA contributions need to stop
- Review pension start date, survivor option, and paperwork
- Set your employer exit timing
3 months out
- Set your first-year income and withdrawal sequence
- Enroll in Medicare or lock your health coverage start date
- Mark your one-time Medigap Open Enrollment window
- Apply for Social Security if benefits start at retirement
- Review beneficiaries and survivor elections
- Download HR, pension, and benefit records
- Review the retirement-year tax picture
- Submit formal retirement notice
1 month out
- Confirm benefit and payroll cutoff dates
- Confirm insurance start and end dates
- Confirm cash for the first few months
- Verify final employer paperwork
- Review workplace retirement-account options
First 30 days retired
- Confirm health coverage is active
- Confirm final paycheck, PTO payout, and benefits ended correctly
- Confirm pension payments started as expected
- Confirm Social Security payments started as expected
- Update RetireRebel with what actually happened
- Leave open space in the first month
90-day reset
- Does your ordinary week still fit what you want?
- Update actual spending, balances, income, and tax withholding