The Pre-Retirement Checklist: What to Confirm in Your Final 1-2 Years of Work
Somewhere between “I’ll retire in a few years” and an actual last day of work, a lot of loose ends need to get tied down, most of them mechanical rather than emotional. This is a practical checklist for that final stretch, the concrete items worth confirming before the paycheck actually stops.
Pin down an actual retirement date, not a rough year
A specific date, not just a general year, changes what’s actually actionable. It determines when to time a Social Security application, when a final 401(k) contribution needs to happen, when healthcare coverage needs to be in place, and when a withdrawal strategy actually needs to start. “Sometime next year” doesn’t let you plan any of that precisely.
Map out your actual retirement budget, not your working budget
A working budget and a retirement budget are rarely the same, commuting costs disappear, but healthcare costs often rise, some categories shrink, others (travel, hobbies, time with family) often grow. This is worth building as an actual number, not an assumption carried over from a working-years budget.
Time your Social Security application
The application needs to happen before benefits start, not on the day you want them to begin, and the exact timing interacts with your specific retirement date and claiming strategy.
Close the healthcare coverage gap
If retirement happens before Medicare eligibility, there needs to be a specific, confirmed plan for coverage in between, COBRA, a marketplace plan, or continued coverage through a spouse’s employer. This is a real cost that belongs in the retirement budget above, not an afterthought.
Finalize your withdrawal sequence
Which accounts get drawn down first, and in what order, taxable, tax-deferred, tax-free, has a real effect on how long savings last and how much tax gets paid along the way. There’s no single right order; the best sequence depends on individual factors such as your tax bracket, account balances, income needs, and other sources of retirement income. This is worth confirming as an actual sequence before the first withdrawal happens, not decided reactively account by account.
Confirm your final paperwork is actually in order
Beneficiary designations, powers of attorney, any pension election forms, and pending employer paperwork (potential 401(k) rollover decisions, unused PTO payout, COBRA election forms) all have real deadlines attached. This is the point to confirm each one is actually complete, not assumed to be handled.
When to bring in outside help
Confirming a withdrawal sequence, timing a Social Security application against a specific date, and building an accurate retirement budget is a lot to coordinate alone, especially in the final stretch before retirement, when the margin for error narrows. As an independent fiduciary, Apriem helps clients coordinate these decisions: building the withdrawal sequence, analyzing Social Security timing, and managing the tax and income timing together, so it isn’t something a client has to piece together on their own.
