Retirement Retirement Planning

Within 3 Months of Retirement? 6 Things to Do Now

Use this quick 90-day checklist to feel more confident about retiring.

By Chris Lewis, CEPF , Edited by Laura Hohenstein

Updated Aug. 5, 2026

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The last three months before retirement can be filled with nerves, both good and bad. Even if you're done with the lion's share of retirement planning, there are usually a few things to finish in the home stretch.

This quick checklist of retirement money moves helps ensure you've covered your bases while inspiring you to think strategically about how different these next years will be.

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Run a tax "test drive" on your first year of retirement income

Sketch out what your income actually looks like in the first year of retirement, using the numbers you gathered from Social Security, pension, RMDs, part-time work, and other sources.

Plug this into tax software for next year, or use an online estimator (if next year's updates aren't available). This shows you if you're under-withholding on Social Security or pensions, or if you're in danger of falling into a higher tax bracket.

Play with the numbers to see how withholding or higher quarterly estimated payments will affect your final tax bill. You may find that a part-time consulting job nets you very little extra income after taxes—but you'll discover it early enough to make changes before the damage is done.

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Triple-check that your income is ready to hit your account

You've likely already confirmed with your employer and benefits administrator when your retirement officially begins. Go through these items once again, just in case:

Social Security Administration: Verify filing and first payment dates, as well as projected benefit amount, through the SSA.gov online dashboard.
Pensions and annuities: Confirm payout type (lump sum or monthly) and the start date of payments.
Employer plans: Check the rollover timing or first withdrawal date for any 401(k) or 403(b) plans to ensure they follow your last paycheck without a gap.

This is also when you should set up withdrawals and direct deposits, so payments move automatically. Consider a test month to make sure a small scheduled withdrawal works successfully, and troubleshoot issues before you truly need the money.

If you can consolidate more of your financial actions (monthly bills, savings plan) with one bank or credit union, do so. You'll appreciate the simplicity as you age.

Prototype your retirement with a trial run

Map out a sample four-week calendar for life after retirement. Ask yourself questions like, "When will I wake up?" and "What people will I spend time with?"

While not specifically financial details, these bigger life questions may matter even more. Retirement can leave some people reeling and unsure what to do next, which can lead to behaviors that negatively impact long-term security.

You might consider a mini-retirement weekend, where you enact strict retirement protocols. Don't check work email, spend only what you would in retirement, and follow through on that "someday" hobby or interest.

Take notes on what you learned with action points for changes you should make. You may find your budget is out of touch or that hobby isn't really all that exciting. It's best to have those eureka moments now while you can comfortably pivot.

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Nail down health care and Medicare details

It's important that you don't have any gaps in health care coverage, which means coordinating plan start and end dates very carefully. Begin by verifying the end of benefits for any employer coverage, whether it's through COBRA, a marketplace plan, or another option.

If you're close to 65, pay close attention to the Medicare Initial Enrollment Period, which starts three months before you turn 65 and ends three months after. If you miss this seven-month window, you may have to wait (possibly going without coverage) and pay penalties on your monthly payment amount afterward.

Enlist help for digital and financial security

The Federal Trade Commission (FTC) reports that from 2020 to 2024, the number of older adults who lost 10,000 dollars or more to impersonation scams increased more than fourfold.

With identity theft and fraud so rampant these days, it's wise to read up on the latest scams. Your state attorney general's website can familiarize you with the most common schemes for your area, and the news bulletins on the FTC.gov website are also a good resource.

Ensure your accounts are secured with multi-factor authentication and devices have a password, PIN, or biometric protection. If a credit monitoring or ID protection service helps you sleep well at night, review the options from reputable web security firms or your bank.

Check in with family

Finally, have some conversations with your loved ones about their expectations for your retirement. These may be your Golden Years, but they do affect people in your circle.

Do your kids expect you to visit more? Are more family holidays on the table? These new but sometimes uncommunicated wishes may take more time (and money) than what you had planned for. Knowing them now and setting reasonable boundaries may be the key to avoiding hurt feelings and a growing travel budget.

Retirement News: Almost 80% of Americans fear a retirement age increase — here’s the real reason why

Bottom line

There is admittedly quite a bit to do before you can sail into full retirement, and many of the things on this list aren't a one-and-done task. If you find you need more time to get retirement-ready, you might be able to delay things for weeks or months.

Otherwise, tightening a few key dials, such as income timing, cash cushion, or paperwork, now is better than doing nothing. Even if they are just a small portion of your much longer to-do list, they can help you avoid major money mistakes.

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