A practical, printable checklist for the year before retirement. Work through income, taxes, healthcare, investments, and estate tasks in the right order—so your first year feels organized, not rushed.
Educational only—not tax or legal advice.
A practical, printable checklist for the year before retirement. Work through income, taxes, healthcare, investments, and estate tasks in the right order—so your first year feels organized, not rushed.
Educational only—not tax or legal advice.
Instant download + email copy
From T-12 to T-0, plus a 30/60/90-day post-retirement section to keep you on track.
Cash-flow setup checklist: taxable → tax-deferred → tax-free, with your "retirement paycheck" plan.
Pre-65 bridge coverage options vs. Medicare windows if you're 65+—know which path applies.
401(k)/403(b) decisions, pension elections, PTO payout, HSA strategy, and stock plan timing.
Titling, TOD/POD designations, trust funding, notary items, and secure digital vault setup.
A shareable overview for your spouse, CPA, and attorney—everyone stays aligned.
A sample of what's covered in the planner—month by month.
Define your target: Set your retirement date, monthly net income goal, and big one-time expenses (move, car, remodel).
Inventory accounts: Taxable, IRA/401(k)/403(b), Roth, HSA, pensions/annuities, and Social Security eligibility.
Start a simple "retirement paycheck" plan: baseline spending + reserves (3–12 months). Review investment policy for the first 3–5 years of withdrawals.
Map withdrawal order: Taxable → tax-deferred → tax-free. Sketch a first-year draw schedule.
List employer benefits that change at retirement: life/DI insurance, retiree health, COBRA options, PTO payout, stock plans.
Begin Roth-conversion or gain-harvesting conversations (if appropriate for your bracket/timeline).
Healthcare planning: If you'll be 65+ at retirement, sketch your Medicare timeline (IEP/SEP/GEP) and drug/doctor needs.
If retiring before 65, compare ACA/private bridge coverage vs. spouse's plan.
Confirm HSA strategy (spend or keep) and how premiums will be paid in retirement.
Keep 1–2 months of extra cash during the transition for unexpected timing gaps.
Use a dedicated "retirement income" checking account for clarity on what's coming in vs. going out.
Name a backup signer on your vault; keep originals with you or your attorney.
Re-read pension survivor choices before finalizing—they're usually irrevocable.
Get the complete 12-month planner with all tasks, plus the shareable one-page summary.
Download the PlannerIdeally 12 months before your target retirement date. If you're closer than that, you can still use the planner—just compress the earlier months and focus on what's most time-sensitive (healthcare, employer notifications, beneficiary updates).
The planner includes a healthcare pathfinder section specifically for pre-65 retirees. Options typically include ACA marketplace coverage, COBRA continuation, a spouse's employer plan, or private insurance. Costs and eligibility vary, so we recommend comparing at least 2–3 options.
A common guideline is 3–12 months of baseline expenses in cash or near-cash. During the actual transition, we suggest keeping 1–2 extra months on hand for unexpected timing gaps (like a delayed pension check or healthcare premium timing).
Not necessarily. There are pros and cons to leaving it in the employer plan vs. rolling to an IRA. Factors include investment options, fees, creditor protection, and whether you might use the "Rule of 55" for early withdrawals. The planner includes a decision framework.
Absolutely. The planner includes a one-page shareable summary designed for couples. Many tasks involve both spouses—pension survivor elections, beneficiary designations, and healthcare decisions all benefit from reviewing together.
Our countdown planner is a starting point. For personalized help with withdrawal strategies, tax projections, healthcare timing, and coordinating all the pieces, schedule a 20-minute introductory call.
Or call us directly: (480) 597-1743
Instant download + email copy