Six Months Out: Capture, Convert, Document

Use the employer benefits you're leaving behind. Most employees forget which benefits will simply expire. Worth doing now:

• Schedule unused medical, dental, and vision appointments while covered by group insurance, before transitioning to ACA or Medicare.
• Spend down the FSA balance — once you separate, unused balances are forfeited (with limited exceptions).
• Maximize HSA contributions for the final year of eligibility.
• Use any remaining tuition reimbursement, professional development budget, or executive coaching benefits.
• Convert vacation balances per company policy — some employers pay out, others let it lapse.
• Take advantage of employee discount programs at retailers (NAPA, Dell, certain travel sites, professional supply stores) before badge access disappears. Make a “last buy” list 60–90 days out.

Set up identity verification while you have multiple verifiable identities. The Social Security Administration, IRS, Medicare, and many state agencies require identity verification (often via ID.me or Login.gov) that's easier to complete while you have an active corporate email, active corporate phone number, recent W-2 income, and active credit relationships. After retirement, the same verification process can take days or weeks longer because the system has less data to match against.

Gather and digitize benefit documents. Pension plan documents, deferred compensation agreements, stock plan summaries, restricted stock vesting schedules, employer retirement plan summary plan descriptions (SPDs), beneficiary designation forms. Make personal copies before access disappears.

Three Months Out: Personal Data and Devices

Separate personal data from work devices. If you've used a company laptop, phone, or cloud account for any personal purpose over the years — photos, family documents, tax records, password managers, side-project files — extract everything before HR locks the device. Most companies revoke access on the last day, sometimes earlier.

• Audit work email for personal correspondence and forward to a personal address.
• Export bookmarks, saved articles, recipes, anything personal saved in the corporate browser profile.
• Move any password manager records to a personal vault — never rely on the corporate password manager after your last day.
• Update two-factor authentication on personal accounts that may be receiving codes via the corporate phone number.
• Clean out personal items from physical office space (you may not have access after the last day).

Plan the laptop transition. If you'll need a personal computer in retirement and have been relying on the company-issued one, buy and set it up while you still have help from corporate IT to migrate any personal files.

Six Weeks Out: Identity, Estate, and Coverage

Update estate documents. Beneficiary designations on the 401(k), IRAs, life insurance, and any deferred compensation should match current intent. Wills, powers of attorney, healthcare directives, and trust documents should be reviewed if they're more than 5 years old or if any major life event has happened since the last update.

Decide on COBRA / ACA / Medicare. Even if you already chose, formalize the enrollment timing. COBRA elections have a 60-day window. ACA marketplace enrollment depends on the loss-of-coverage qualifying event. Medicare enrollment has hard windows that affect lifetime premium costs.

Address professional licenses and memberships. If you carry a CPA, PE, attorney bar admission, or medical license that you intend to maintain, decide on inactive vs. retired vs. continued status. Some have meaningful CE requirements; some have one-time elections that lock in for life. Professional association memberships often have retired-member discounts you should know about.

The Last 30 Days

Final 401(k) actions. Confirm your final contributions and any employer match true-up. Decide whether to leave the 401(k) at the employer plan, roll to an IRA, or take advantage of the Rule of 55 (if separating in or after the year you turn 55). The Rule of 55 only applies to the 401(k) at the employer you're separating from, and rolling it before retirement forfeits that access.

Schedule deferred compensation distributions. If you have NQDC, the distribution election was usually made years earlier — but the timing of the first payment depends on separation date. Verify the distribution will land in the tax year you intended.

Notice and relationships. Give notice in a way that preserves long-term professional relationships. The colleagues you leave behind today are the people you'll consult, board with, refer to, or work alongside in some other capacity over the next 20 years. The retirement-from-this-job decision shouldn't look like the retirement-from-this-field decision unless they actually are the same.

Real Scenario: Tango, 60M, Summer Retirement

Six months out, Tango ran the standard checklists for financial planning, healthcare, and Social Security. Two months out, he added the operational checklist:

• Made the NAPA last buy: stocked up on oil, air, and cabin filters at the company-discounted price.
• Bought a personal laptop and migrated personal files from the work machine over a weekend.
• Used 8 weeks of dental, vision, and physical-therapy appointments before group coverage ended.
• Set up ID.me, IRS online account, and SSA online account while still actively employed and easily verifiable.
• Updated 401(k), IRA, and life insurance beneficiary designations to reflect current family situation.
• Switched professional society membership to a retired-member rate.
• Maxed final HSA contribution and made a list of qualified medical expenses for future tax-free reimbursement from the HSA.

None of these items are financial decisions. Collectively they saved several thousand dollars and avoided most of the administrative friction that typically eats up the first 60–90 days of retirement.

The First 90 Days: A Different Kind of Plan

The first 90 days of retirement are where the lifestyle adjustment happens. Many retirees experience a brief euphoria, then a slump, then a normalization. Households that plan for the transition explicitly tend to handle it better.

• Plan something to retire to — not just from.
• Keep the routine intact for the first month: same wake time, a few standing appointments per week.
• Schedule a financial check-in 60–90 days in to make sure the withdrawal plan is operating as designed.
• Identify two or three people you'll see weekly that aren't spouse or family — replacing the social structure work provided.

Common Mistakes

• Letting employer benefits expire because nobody made the list of what was about to disappear.
• Failing to separate personal data from the company laptop before the last day.
• Skipping identity verification setup until after retirement and then spending weeks re-establishing access.
• Rolling the 401(k) to an IRA before separation and forfeiting Rule of 55 access.
• Underestimating the volume of administrative work in the first 60 days of retirement.
• Treating the financial plan as the entire retirement plan and ignoring the lifestyle transition.

The Bottom Line

The financial checklist solves the strategic question — can I retire, and how. The operational checklist solves the friction problem — what do I do in the months around the transition so the first year of retirement isn't a paperwork blur.

Neither checklist by itself is complete. The retirements that feel smooth are usually the ones where both got done deliberately.