The 12 months before retirement are the highest-leverage year of your financial life. Nearly every decision you'll rely on for the next 30 years is set up during this window. Here is the month-by-month sequence we walk clients through, in the order the deadlines actually arrive.
Months 12–9: The picture
Build the retirement income plan. Start with sources: Social Security (his and hers), any pensions, portfolio withdrawals, part-time income, rental income, annuities. Then timing: what turns on when. Then tax character: which dollars are pre-tax, Roth, or taxable, and how that shapes the withdrawal order.
Stress-test spending against a bad first three years. If the plan only works when markets cooperate, it isn't a plan.
Confirm the retirement date with your employer. Understand any pension elections, deferred compensation payout schedules, restricted stock or option vesting, unused PTO payout timing, and whether any of these push you into a higher tax bracket in the final year.
Get a baseline physical. Your out-of-pocket healthcare exposure changes on the retirement date; know what you're managing.
Months 9–6: The moving parts
Decide Social Security claiming strategy for both spouses. Not just 'when' but 'in what order' — each spouse's filing date interacts with the other's.
Map the healthcare bridge from retirement to Medicare at 65. COBRA (up to 18 months, expensive but preserves the same network), ACA marketplace (subsidies phase out at higher incomes and interact with Roth conversions), spousal coverage from a still-working partner, or retiree health from the employer if offered.
Review beneficiary designations on every retirement account, life insurance policy, transfer-on-death brokerage account, and HSA. These override your will. This is where estate mistakes hide.
If you'll be 65 within a year of retirement, start reading about Medicare. It's more complex than expected and the deadlines are punitive.
Months 6–3: The tax moves
Max out final-year contributions: 401(k) ($24,500 in 2026, plus $8,000 catch-up at 50+, plus a $12,000 super-catch-up at ages 60–63), HSA if eligible ($4,400 self / $8,750 family in 2026, plus a $1,000 catch-up at 55+), and a backdoor Roth if applicable.
Model whether a partial Roth conversion late in the final work year makes sense. Usually not — you're at peak income. But sometimes deferred comp lands the following year and creates a one-year gap worth using.
Confirm the tax withholding plan for the first year of retirement. Under-withholding triggers estimated tax penalties; over-withholding leaves cash idle. Neither is fatal, but both are avoidable.
Harvest capital gains at 0% if your projected first-year taxable income keeps you under the threshold ($99,750 MFJ in 2026 for the 0% long-term capital gains bracket). This is a narrow window that often closes once Social Security begins.
Months 3–0: The logistics
Enroll in Medicare if turning 65 in your window. Miss the Initial Enrollment Period without creditable coverage and Part B carries a permanent penalty.
Decide whether to roll the 401(k) to an IRA. This is not automatic — the 401(k) may offer better creditor protection, lower institutional fund expense ratios, or Net Unrealized Appreciation treatment on employer stock. Some 401(k)s allow penalty-free withdrawals at 55; IRAs don't.
Set up the withdrawal cadence. Establish a checking account funded from the portfolio, decide monthly vs. quarterly, automate it. Make the first month of retirement feel identical to the last month of work — same date, same amount, same account.
Build the 12–24 month cash buffer. This is what lets you ignore a bad market in year one.
Say the goodbyes. This isn't a financial task, but it's the one people regret most when they skip it.
The first 90 days of retirement
Do not restructure the portfolio in the first 30 days. You are recovering from a major transition; make no permanent decisions from a temporary emotional state.
Review the actual spending in month one against the plan. Adjust the withdrawal amount at 90 days based on real data, not the pre-retirement estimate.
Update the estate plan to reflect the new reality — new address if you moved, updated beneficiary contingents, revised health care directives.
The best retirements are boring on day one because the real work was done in the twelve months prior. Sequence the checklist against the calendar, not against enthusiasm.