The first three months set the tone for the next thirty years. One bite at a time.
Confirm final paycheck and unused PTO payout
HR processes a final paycheck within 1-3 weeks. Confirm the amount and how unused vacation is paid out. Some states require immediate payout, others 14-30 days.
Close out work email and contacts
Export important personal contacts. Forward critical email to your personal account. Save any documents you have permission to keep.
Decompress - first week is for rest
The first week feels like a long weekend. Around day 8 reality sets in. That is normal. Plan a low-key week. Do not start new projects yet.
Tell key contacts you have retired
Doctor's office, bank, insurance company, and pharmacy may have your work phone or email on file. Update each one with your personal contact information.
Decide on Medicare or gap coverage
If you are 65+, Medicare A is automatic. Sign up for B and D. If you retire before 65, choose between COBRA (your old plan for 18 months, expensive), ACA marketplace (subsidies based on income), or a spouse's plan.
Decide 401(k) - stay or roll over
You can leave it with your employer, roll to an IRA (more investment choices, more flexibility), or roll to a new employer plan. A flat-fee fiduciary advisor charges $300-$600 to walk you through tradeoffs.
Apply for Social Security if you have decided
Most retirees do this in person at the local SSA office or online at ssa.gov. The timing decision is huge - check our SS Claiming Age Chart tool before you file.
Sign up for or cancel work-related subscriptions
LinkedIn Premium, professional society memberships, work expense apps. Decide which to keep personally. Some membership rates drop after retirement.
Build a weekly schedule
No workday means no structure unless you build one. Pick three anchors: morning walk, weekly volunteer shift, weekly social. Three anchors keep depression at bay better than a long to-do list.
Plan a meaningful first month-3 project
Pick one thing you put off for years - a hobby, a trip, a class, learning an instrument. Block the first weeks of months 2-3 for it. This is your reward.
Reconnect with neighbors and old friends
Working life filtered out a lot of casual contacts. Now is the time. Make a list of 10 people you have lost touch with. Call one a week.
Update emergency contacts everywhere
Your work emergency contact is no longer the right one. Update at doctors offices, pharmacy, banks, and your phone's emergency screen.
Re-do your beneficiaries on every account
IRA, 401(k), life insurance, pension survivor option. Marriage and divorce change things. Make sure each form reflects your current wishes.
Update or write your will and healthcare proxy
If you have not touched these in 5+ years, refresh them. An attorney charges $300-$600 for a basic update. AARP and your state bar have free legal aid for low-income seniors.
Build a retirement budget you can actually live on
Track 60 days of real spending. Compare to projected SSA + pension + IRA withdrawals. Adjust before the gap becomes a problem. A flat-fee advisor can stress-test it.
Consider downsizing or aging-in-place upgrades
Many retirees know within 90 days whether the current home still fits. Aging-in-place upgrades (grab bars, walk-in shower, lever door handles) typically cost $2,000-$8,000 and add years of independence.