Countdown to Retirement

A year-by-year tech checklist — five phases, from five years out to six months in. Do a few items each phase and the transition stays calm.

About 20 minutes per phase. Print the kit and tick boxes as you go.

Countdown to Retirement Tech Checklist

Five phases, from five years out to six months in — TekSure.com

Long runway means small habits stick. Start the digital cleanup now and the last year is calm, not frantic.

☐Open a my Social Security account at ssa.gov. Sign up at ssa.gov/myaccount and check your earnings record. Errors take months to fix, so finding them now beats finding them at 64. See our Social Security Setup tool for screenshots.
☐Inventory every online account in a password manager. Bitwarden, 1Password, or iCloud Keychain — pick one. Add every login as you use it for 30 days. By month two you will have a full list. This becomes the master list for everything else later.
☐Move work email contacts to a personal address. Anyone you want to keep in touch with — friends, doctors, family — should have your personal Gmail, iCloud, or Outlook address. Work email vanishes the day you retire.
☐Start backing up phone and computer to the cloud. iPhone: Settings, your name, iCloud, iCloud Backup, On. Android: Settings, Google, Backup, On. PC: turn on OneDrive. Mac: turn on iCloud Drive. Five years of muscle memory means nothing gets lost in the transition.

Medicare enrollment opens 3 months before your 65th birthday. The decisions you make now lock in for a year at a time.

☐Create a Medicare.gov account. Go to medicare.gov and click "Log in / Create account". You will need your Social Security number. The portal is where you compare Part D drug plans, Medicare Advantage plans, and track claims later.
☐Download and save important work files. Anything personal on a work laptop — photos, personal documents, contact lists — copy to a USB drive or personal cloud. IT wipes the device the day you leave.
☐List recurring subscriptions paid through work. LinkedIn Premium, professional newsletters, software that came through work email — note which you want to keep and move them to personal billing now.
☐Update beneficiaries on every retirement account. 401(k), IRA, pension, life insurance. Each plan has its own beneficiary form. Log into each provider, find "Beneficiaries", confirm or update. Old ones pointing to ex-spouses cause real problems for families.
☐Plan your Medicare plan comparison. Bookmark our Medicare Plan Chooser. The official Medicare Plan Finder at medicare.gov/plan-compare opens during enrollment.

This is enrollment season. Move carefully — there are scammers waiting, and good decisions need a quiet head.

☐Enroll in Medicare during your Initial Enrollment Period. Your window is 7 months — 3 before your 65th birthday month, your birthday month, and 3 after. Sign up at ssa.gov/medicare. Missing this window means a permanent late penalty on Part B.
☐Compare Part D drug plans against your prescriptions. On medicare.gov/plan-compare, type in every medication you take. The tool ranks plans by your actual yearly cost. The cheapest plan for someone else may be the most expensive for you.
☐Set up a personal email signature with your new contact info. Phone, personal email, mailing address. Send it once to friends, family, doctors, and the pharmacy so the work address can quietly retire with you.
☐Forward work calendar items to personal calendar. Doctor appointments, family birthdays, recurring reminders that lived on the work calendar — copy them to Google Calendar or Apple Calendar before access ends.

The work laptop is gone. The work email is gone. This month is about making sure everything important still works.

☐Print your Medicare card and store the digital one in your phone wallet. Your red, white, and blue card arrives by mail. Photograph the front and back, save to your phone Notes app, and add to Apple Wallet or Google Wallet if your providers accept it.
☐Set up the patient portal for every doctor. MyChart, FollowMyHealth, Patient Gateway — sign in once for primary care, dentist, eye doctor, specialists. Test results and appointment booking live there.
☐Switch any work-tied two-factor codes. If your bank, brokerage, or 401(k) sent text codes to a work phone, change the number to your personal cell. Same for any email-based 2FA pointing at the work address.
☐Review the password manager and clean up. Delete logins for tools you only used at work. Update names so a family member could find what they need. This list is the single most useful thing you can leave behind.

The settling-in is done. Now lock in the long-term setup so retirement stays calm for years.

☐Schedule an annual digital check-in with a family member. Once a year, sit with an adult child or trusted person and walk through the password manager, beneficiary list, and emergency contacts. Put it on the calendar so it actually happens.
☐Set up legacy contacts on your phone and email. iPhone: Settings, your name, Sign-In and Security, Legacy Contact. Google: myaccount.google.com, Inactive Account Manager. They can access your data if something happens.
☐Review every monthly subscription against actual use. Streaming, magazines, cloud storage, software. Cancel what you do not use. Retirement income usually shrinks — small monthly bills add up to real money.
☐Set up a low-cost cell phone plan for retirees. Consumer Cellular, T-Mobile 55+, Verizon 55+ Unlimited, and AARP-discount plans drop most bills by half. The phone you have keeps working — only the SIM or eSIM changes.
☐Read our Account After Loss guide together. Hard to think about, important to plan. Walk through what a spouse or child would need to access if something happened to you.