Here is the short answer. A good pre-retirement checklist covers nine decisions, and each one has a deadline counted back from your last day of work: 90, 60, or 30 days out. They are final pay and bonus timing, deferred compensation and equity elections, your pension election, your 401(k), Social Security, Medicare and IRMAA, health coverage before 65, a cash reserve, and beneficiaries.
When you have a set retirement date, planning turns into deadlines. Some elections are hard to change after you leave, and a missed Medicare window can follow you for life. We built this pre-retirement checklist to put every date in one place. If you are still choosing a claiming age, start with our guide to when to claim Social Security.
Four groups cover the checklist:
1. Pay, deferred compensation, and equity
2. Pension, 401(k), and Social Security
3. Medicare and health coverage
4. Cash reserve and beneficiaries
Your Pre-Retirement Checklist at a Glance
| Task | Deadline | Why it matters |
|---|---|---|
| Group 1: Pay, deferred compensation, and equity | ||
| 1. Confirm final paycheck, PTO payout, and bonus timing | 90 days out | Some bonus plans require you to be employed on the payment date. Pay can also land in a different tax year than you expect. |
| 2. Make deferred compensation and equity elections | 90 days out | Deferred compensation timing is set by your plan and hard to change later. Stock options can expire soon after you leave. |
| Group 2: Pension, 401(k), and Social Security | ||
| 3. Request pension estimates, then choose lump sum or annuity | Estimates at 90 days out; elect at 60 days out | A married participant needs spousal consent to pick anything other than the joint-and-survivor annuity. The form you choose sets lifetime income. |
| 4. Decide whether to roll over or leave your 401(k) | 60 days out | A direct rollover avoids 20% mandatory withholding. Leaving your employer at 55 or later can open penalty-free access to that plan. |
| 5. Set your Social Security claiming plan | 60 days out | Claiming at 62 cuts your benefit by 30% if your full retirement age is 67, and each year of delay past that adds 8% up to age 70. |
| Group 3: Medicare and health coverage | ||
| 6. Map Medicare enrollment windows and IRMAA exposure | 90 days out | Your enrollment window is built around age 65, and a late penalty can last as long as you have Part B. IRMAA is based on income from two years earlier. |
| 7. Line up health coverage if you retire before 65 | 60 days out | COBRA must be elected within a set window and lasts up to 18 months. It does not count as employer coverage for Medicare's later enrollment window. |
| Group 4: Cash reserve and beneficiaries | ||
| 8. Fund a 12 to 24 month cash reserve | 60 days out | Cash covers spending, so a market drop in your first years does not force you to sell investments. |
| 9. Update beneficiaries on every account | 30 days out | Beneficiary forms, not your will, decide who receives most retirement accounts and insurance. |
Table 1: Your pre-retirement checklist, with each deadline counted back from your last day of work.
Group 1: Pay, Deferred Compensation, and Equity
Start here, because this group has the fewest second chances. We suggest asking HR in writing when your final paycheck, PTO payout, and any bonus will be paid, and whether leaving before the bonus date forfeits it. Employers often withhold supplemental pay such as bonuses at a flat 22% on the first $1 million, which may differ from your actual bracket, so plan for a true-up at tax time.1
Next, pull your deferred compensation and equity agreements. Under Section 409A, deferred compensation can be paid on set events such as separation from service. A later change generally must be made at least 12 months before the scheduled payment and push it back at least five years, and key employees of public companies may face a six-month delay before payments begin.2 If you hold incentive stock options, you generally need to exercise within three months of leaving to keep their tax treatment.3 Also check vesting terms for restricted stock units and options, since some awards are forfeited when you leave.
Group 2: Pension, 401(k), and Social Security
Request your pension estimates at 90 days and make the election at 60 so you have time to compare. Most defined benefit plans default to a joint-and-survivor annuity, and a married participant needs the spouse's written consent to choose a lump sum or another form.4 Run both options against your full plan before you sign, because the payment form sets your income and what your spouse keeps.
For your 401(k), a direct rollover moves the money with no withholding. A check made out to you triggers 20% mandatory withholding, and any amount you do not redeposit within 60 days is taxable and may face the 10% early distribution tax.5 If you leave your employer in or after the year you turn 55, distributions from that employer's plan can avoid the 10% tax, but an IRA does not offer that exception, so rolling over can close the door.6
If you were born in 1960 or later, your full retirement age is 67. Claiming at 62 reduces your benefit by 30%,7 and each year you delay past full retirement age adds 8% until age 70.8 You can generally apply while still working,9 so settle your date before your last day.
Group 3: Medicare and Health Coverage
Medicare's initial enrollment period lasts seven months: the three months before your 65th birthday month, the month itself, and the three months after. If you keep working past 65 on employer coverage, you get an eight month special enrollment period after that coverage or employment ends, but COBRA does not count as employer coverage for this purpose.10 Missing the window adds 10% of the standard Part B premium for each full 12 months you could have enrolled, and the penalty generally lasts as long as you have Part B.11
IRMAA is the other trap. Medicare uses your tax return from two years earlier, so your final high-earning years set your premiums after you stop working. Bonus payouts, deferred compensation distributions, and a pension lump sum you do not roll over can all push income higher. For 2026, surcharges begin above $109,000 of modified adjusted gross income for single filers and $218,000 for joint filers. Stopping work counts as a life-changing event, so you can ask the Social Security Administration to use a lower income figure with Form SSA-44.12 Our IRMAA article explains the tiers.
If you retire before 65, you need a bridge. COBRA gives you at least 60 days to elect and can last up to 18 months,13 though you may pay up to 102% of the plan's cost.14 A Marketplace plan is the alternative, and you can enroll from 60 days before your coverage ends to 60 days after.15 Compare both before your last day, because that window closes quickly.
Group 4: Cash Reserve and Beneficiaries
A reserve of 12 to 24 months of spending gives you a buffer during the early years, when a market drop does the most damage. If you spend $15,000 a month after tax, that means $180,000 to $360,000. Net out pension and Social Security income, fund the reserve before your paycheck stops, and hold it in Treasury bills, money market funds, or insured cash.
Finish with beneficiaries. A beneficiary form usually overrides your will, so update every 401(k), IRA, life insurance policy, HSA, and annuity, along with the survivor option on your pension. A new rollover IRA needs fresh forms, and as noted above, plan rules can require your spouse's consent to name someone else.
Talk Through Your Last 90 Days
A checklist tells you what is due, and a review shows how the choices fit together. If it would help to talk through yours, the team at Journey Advisory Group, led by Eric Pettway, CFA, is glad to walk through a pre-retirement review with you. As fee-based fiduciaries, we build the plan alongside your CPA and attorney. You can reach us at info@JourneyAdvisory.Group or 800-749-7143, and you can find more guides in our life transitions hub.
Disclosure
This material prepared by Journey Advisory Group, LLC is for informational purposes only. It is not intended to serve as a substitute for personalized investment, tax, or legal advice, or as a recommendation or solicitation of any particular security, strategy, or investment product. Facts presented have been obtained from sources believed to be reliable. Journey Advisory Group, however, cannot guarantee the accuracy or completeness of such information, and certain information may have been condensed or summarized from its original source.
SEC Registration does not constitute an endorsement of the firm by the SEC nor does it indicate that the advisor has attained a particular level of skill or ability. Securities investments contain risks including the possible loss of principal. Neither asset allocation nor active management guarantee a profit or protection from loss.
Journey Advisory Group is a fee-based advisory firm and SEC-registered Registered Investment Adviser (RIA). Additional information about Journey Advisory Group's services, fees, and potential conflicts of interest is available in Form ADV Parts 2A and 2B, which can be obtained through the SEC's Investment Adviser Public Disclosure website at adviserinfo.sec.gov or by contacting the firm directly.
JAG does not provide tax or legal advice, and nothing contained in these materials should be taken as tax or legal advice.
References
1. Internal Revenue Service. "Publication 15 (2026), Employer's Tax Guide." https://www.irs.gov/publications/p15
2. Thompson Coburn. "Section 409A: Top 10 Rules for Compliant Non-Qualified Deferred Compensation." https://www.thompsoncoburn.com/insights/publications/item/2016-07-28/section-409a-top-10-rules-for-compliant-non-qualified-deferred-compensation
3. Cornell Law School Legal Information Institute. "26 U.S. Code § 422: Incentive Stock Options." https://www.law.cornell.edu/uscode/text/26/422
4. Internal Revenue Service. "Fixing Common Plan Mistakes: Failure to Obtain Spousal Consent." https://www.irs.gov/retirement-plans/plan-sponsor/fixing-common-plan-mistakes-failure-to-obtain-spousal-consent
5. Internal Revenue Service. "Rollovers of Retirement Plan and IRA Distributions." https://www.irs.gov/retirement-plans/plan-participant-employee/rollovers-of-retirement-plan-and-ira-distributions
6. Internal Revenue Service. "Topic No. 558, Additional Tax on Early Distributions from Retirement Plans Other Than IRAs." https://www.irs.gov/taxtopics/tc558
7. Social Security Administration. "Retirement Benefits Planner: Reduction for Retiring Early." https://www.ssa.gov/benefits/retirement/planner/agereduction.html
8. Social Security Administration. "Retirement Benefits Planner: Delayed Retirement Credits." https://www.ssa.gov/benefits/retirement/planner/delayret.html
9. Social Security Administration. "Learn About Retirement Benefits." https://www.ssa.gov/benefits/retirement/learn.html
10. Medicare.gov. "When Does Medicare Coverage Start?" https://www.medicare.gov/basics/get-started-with-medicare/sign-up/when-does-medicare-coverage-start
11. Medicare.gov. "Avoid Penalties." https://www.medicare.gov/basics/costs/medicare-costs/avoid-penalties
12. Social Security Administration. "Medicare Premiums: Rules for Higher-Income Beneficiaries." https://www.ssa.gov/benefits/medicare/medicare-premiums.html
13. U.S. Department of Labor. "An Employee's Guide to Health Benefits Under COBRA." https://www.dol.gov/sites/dolgov/files/ebsa/about-ebsa/our-activities/resource-center/publications/an-employees-guide-to-health-benefits-under-cobra.pdf
14. U.S. Department of Labor. "COBRA Continuation Coverage." https://www.dol.gov/general/topic/health-plans/cobra
15. HealthCare.gov. "Special Enrollment Period (SEP)." https://www.healthcare.gov/coverage-outside-open-enrollment/special-enrollment-period/