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Before you retire, run this checklist
Retiring well is mostly about not missing anything. This walks the big decisions, from cash
flow and healthcare to taxes and your estate, so nothing important slips through. Check off
what you've handled, and save a copy to bring to your advisor.
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Cash flow Will your income and expenses change in retirement? Build a fresh income-and-spending plan for your first few years off the paycheck. Do you have a pension? Compare the payout options (single life, joint, lump sum), and coordinate it with Social Security and any life insurance. Could you be forgetting a pension or benefit from a past employer? Old plans are easy to lose track of. Track them down before you retire. Are you retiring early? Before full retirement age, Social Security is reduced if you earn over $24,480 (or $65,160 in the year you reach FRA). Claiming before FRA also permanently lowers the benefit. And you can tap a 401(k) penalty-free if you leave that employer at 55 or later. Are you married? Spousal claiming strategies can raise your household's lifetime Social Security. Were you married before and are now single? An ex-spouse's record can pay you if the marriage lasted 10 or more years; a late spouse's record can pay survivor benefits. See the survivor-benefits guide. Healthcare & insurance Are you retiring before 65 and need coverage? Medicare doesn't start until 65. A Marketplace plan can bridge you, and you may qualify for a premium tax credit, but watch the income cliff near 400% of the federal poverty level. See the healthcare-transition guide. Will you lose employer coverage when you retire? Under 65, look at COBRA or the Marketplace. At 65 or older, enroll in Medicare on time. Do you need extra coverage like vision or dental? Medicare leaves most of it out, so price standalone options. Are you contributing to an HSA? Once you enroll in Medicare you can no longer fund an HSA, so plan the timing. Will your income (MAGI) top $109,000 single or $218,000 married? Above those lines, Medicare adds IRMAA surcharges to your Part B and Part D premiums, based on your income from two years earlier. Are you disabled? You may qualify for certain benefits or earlier access to them. Have your life insurance needs changed? What you needed while working and raising a family may not match retirement. Are you thinking about long-term care? Weigh traditional LTC insurance, self-funding, and hybrid policies. If you already have a policy, confirm it still fits. Assets & debt Do you hold stock options, grants, or RSUs? Retiring can change your rights, your taxes, and your cash flow, so map it out before you leave. Are your investment goals or risk tolerance shifting? The portfolio that got you here usually isn't the one that carries you through retirement. Do you own a business? You'll want an exit or succession plan well before you stop working. Do you hold annuities or illiquid assets? Review how and when you can actually access them. Do you have a loan against an employer retirement plan? Plan to pay it off, since leaving can trigger repayment or taxes on the balance. Do you have a deferred compensation plan? Coordinate its payout with your other income to manage the tax hit. Do you have several similar accounts (multiple 401(k)s or IRAs)? Consolidating can simplify both your life and your RMDs. Are you planning to move? A new state can change your taxes, your cash flow, and your Medicare Advantage network. Taxes Do you expect large required minimum distributions later? Roth conversions in your lower-income years can shrink the future RMD and the tax bill it brings. Will your income drop once you retire? That low-income window is often the best time for Roth conversions at a lower rate. Are you or your spouse 65 or older? The 2026 senior deduction ($6,000 per eligible person) can free up room for Roth conversions or gain harvesting. Mind the income phaseouts. Estate & long-term Could your estate exceed the federal exemption ($15M, or $30M for a couple)? If so, estate-tax planning is worth starting early. Are you charitably inclined? Tax-smart giving, like donating appreciated stock or using a donor-advised fund, can do more for less. Is your estate plan old or possibly outdated? Check that your beneficiaries and the people you've named (trustee, power of attorney) still reflect your life today. Do your account beneficiaries need updating? This covers retirement plans, life insurance, and transfer-on-death accounts, which all pass outside your will. Other Do you have unused vacation days? You may be able to use them before you go, or get paid out for them. Are there state-specific rules to consider? Some states tax retirement income very differently, so know how yours treats it.
A starting point, not personal advice. Your situation may add items or change the priorities.
When a decision is high-stakes, walk it through with a planner before you act.