Your Retirement Planning Checklist: What to Do 10 Years, 5 Years, and 1 Year Before You Retire
“By failing to prepare, you are preparing to fail.”
-Benjamin Franklin
Retirement doesn’t happen all at once. Neither should your planning.
The steps you take at 55 are different from the steps you take at 64. Miss something important along the way and you could end up scrambling — or worse, leaving money on the table.
I’ve helped hundreds of people retire over nearly 30 years. The ones who feel most confident aren’t the ones with the most money. They’re the ones who planned ahead at each stage.
Here’s a checklist for each phase of the retirement countdown.
10+ Years From Retirement: Build the Foundation
You still have time. But time goes fast. Use it wisely.
☐ Pick a target retirement age. You don’t need an exact date. But you need a number. Are you aiming for 62? 65? 67? Everything else flows from this.
☐ Estimate how much you’ll need. A common rule of thumb is 25 times your annual expenses. If you spend $100,000 a year, that’s $2.5 million. Another benchmark: aim to replace 70-80% of your pre-retirement income. Your number can vary, so think about HOW you want to live in retirement. That should help you get more clear about your income needs.
☐ Check your current savings against that goal. Log into your 401(k), IRA, and brokerage accounts. Add it all up. How close are you? If you’re behind, you still have time to catch up — but you need to know where you stand.
☐ Review your investment strategy. Are you taking enough risk to grow your money? Too much risk for your timeline? Asset allocation matters more than stock picking. If you’re not sure, this is a good time to get a second opinion.
☐ Look at your debt. Will you be debt-free by retirement? If you’re carrying a mortgage, car loans, or other debt, map out when it will be paid off. Entering retirement with no debt gives you a lot more flexibility. Keep in mind, some debt could be ok to have. I have seen people with a 2.5% home mortgage. That may be better to keep than to pay off. Your risk tolerance has a say in this too.
☐ Think about healthcare costs. Medical expenses usually go up after you stop working. Have you factored that into your estimates? Do you have long-term care insurance — or a plan to self-insure?
☐ Consider life insurance. If your spouse or dependents rely on your income, will your retirement savings be enough for them if something happens to you? Or do you need a death benefit to fill the gap? If you are close to hitting your retirement goals, then you may not need it. But double check just to make sure.
☐ Max out your retirement accounts. In 2026, you can contribute $24,500 to a 401(k) — or $32,500 if you’re 50 or older. For IRAs, it’s $7,500 — or $8,600 if you’re 50+. If you’re not maxing out, you’re leaving tax-advantaged growth on the table.
5 Years From Retirement: Get Specific
The finish line is in sight. Time to get serious about the details.
☐ Set a target retirement date. Not just a year — Pick a specific season or even a specific month. This makes everything else more concrete.
☐ Decide where you’ll live. Will you stay in your current home? Downsize? Move to a lower-cost area? Your location affects your cost of living, your taxes, and your access to healthcare.
☐ Total up all your resources. Add up everything: 401(k)s, IRAs, Roth accounts, brokerage accounts, real estate, pensions, Social Security estimates. This is your retirement income machine. Is it big enough?
☐ Stress-test your plan. What happens if the market drops 30% in your first year of retirement? What if you live to 95? What if healthcare costs more than you expect? Run the scenarios now — not after you’ve quit your job.
☐ Start shifting to lower-risk investments. You don’t want a market crash to derail your retirement right before you stop working. Consider moving some assets to bonds or cash equivalents to reduce volatility.
☐ Decide when you’ll claim Social Security. You can claim as early as 62 or as late as 70. The longer you wait, the higher your monthly benefit. For someone eligible for the maximum benefit, that’s the difference between $2,831/month at 62 and $5,108/month at 70. This decision is permanent — don’t rush it. THIS IS IMPORTANT: think through not only YOUR benefit, but how it will affect your spouse’s benefit too. This one decision can mean $200,000 or more over the course of your lifetime.
Real financial planning for real life.
Riverbend is a fee-only, fiduciary advisor. Our plans are personal, shaped by your values and designed to help you build a full life.
Who We Are☐ Learn about Medicare. You’re eligible at 65, even if you don’t retire until later. Understand the difference between Original Medicare and Medicare Advantage. Know the enrollment windows. Late enrollment penalties can follow you for life.
☐ Think about your withdrawal strategy. Which accounts will you draw from first? In what order? This affects your taxes, your Social Security, and how long your money lasts. It’s not something to figure out on the fly.
1 Year From Retirement: Handle the Details
You’re almost there. Now it’s about execution.
☐ Apply for Social Security. If you want benefits to start when you retire, apply a few months early. You can do it online at ssa.gov, by phone, or in person. Don’t wait until the last minute. BUT, as I mentioned previously, think about how that affects your family’s overall lifetime income. You may be able to still retire and bridge the gap, to maximize your benefits.
☐ Enroll in Medicare. Your initial enrollment period starts three months before you turn 65 and ends three months after. Miss that window and you’ll pay higher premiums — permanently.
☐ Coordinate with your employer’s health insurance. Know exactly when your coverage ends. Make sure there’s no gap between your employer plan and Medicare. If your employer offers retiree health benefits, understand what they cover and what they cost.
☐ Finalize your drawdown plan. Know exactly where your income will come from each month. Social Security. Pension. IRA withdrawals. Brokerage account dividends. Map it out so you’re not guessing.
☐ Review your tax strategy. Your first few years of retirement are often your best opportunity for Roth conversions and other tax moves. Plan ahead so you don’t miss the window.
☐ Update your estate documents. When’s the last time you reviewed your will, trust, powers of attorney, and beneficiary designations? Retirement is a good trigger to make sure everything is current.
☐ Tell your employer. Give appropriate notice. Understand your options for any deferred compensation, stock options, or pension elections. Get everything in writing.
The Bottom Line
Retirement planning isn’t a single event. It’s a series of decisions spread over years — sometimes decades. And rules change, make sure your plan is nimble enough to change with it.
The earlier you start thinking about these questions, the more options you’ll have. And the closer you get to retirement, the more important it is to get the details right.
If you’re not sure where you stand, now is the time to find out.
