What to Do Six Months Before Retirement: Checklist

The final six months before retirement are some of the most important. During this window, you’ll want to fine-tune your income plan. This means you should assess your tax exposure, make sure your investment mix supports your goals and double-check your paperwork. Even if you’ve been planning for years, the last stretch before retirement is when all the pieces start to come together, or fall apart. And a structured checklist can make all the difference.

A financial advisor can help you review your income sources, test different withdrawal strategies and confirm that your plan stays aligned with your retirement goals.

1. Revisit Your Asset Allocation

Your investment strategy should evolve as you approach retirement. At this stage, your focus typically shifts from growth to preservation and income. That means reassessing your portfolio to ensure your asset allocation matches your changing risk tolerance.

For example, someone who has spent decades investing in a 70% stock and 30% bond portfolio might decide that level of stock exposure no longer matches their risk tolerance or withdrawal needs. A different mix could reduce exposure to market losses, although holding fewer stocks can also reduce the portfolio’s potential for long-term growth.

Investment Tip: Use this time to rebalance your accounts across IRAs, 401(k)s and taxable investments. Review the portfolio as a whole so that changes in one account do not unintentionally alter your overall allocation.

2. Create or Finalize a Withdrawal Strategy

Knowing how and when you’ll tap into your retirement accounts is just as important as knowing how much is in them. A well-thought-out withdrawal plan can help minimize taxes, extend the life of your investment portfolio and provide a framework for covering expenses.

For example, someone with $800,000 spread across a traditional IRA and Roth IRA could compare withdrawals from both accounts rather than automatically emptying one before using the other. Traditional IRA distributions generally increase taxable income, while qualified Roth IRA withdrawals generally do not. The amount taken from each account can therefore affect income taxes and Medicare premiums later in retirement.

Investment Tip: Consider the order of withdrawals, the impact on your tax bracket and how required minimum distributions (RMDs) will affect your plan later. Under current guidance, people born from 1951 through 1959 generally begin RMDs at 73, while people born in 1960 or later generally begin at 75.

3. Review Your Tax Plan

A retiree reviews tax-saving strategies like Roth conversions and withdrawal timing to help reduce long-term tax costs.

If you’ve built up significant retirement savings, now is the time to explore strategies that could reduce your long-term tax liability. This includes Roth conversions, tax-loss harvesting and carefully timing withdrawals.

Let’s say you’re in a lower tax bracket now but expect higher income later due to RMDs or Social Security. Converting $30,000 per year from a traditional IRA to a Roth IRA before RMDs kick in could reduce your future taxable income. The conversion itself generally creates taxable income in the year it is completed, so compare the immediate tax cost with the potential effect on future withdrawals and RMDs.

For 2026, the standard deduction is $16,100 for single filers, $32,200 for married couples filing jointly and $24,150 for heads of household. Federal income tax brackets range from 10% to 37%, so the amount of a Roth conversion or taxable withdrawal can affect the marginal rate applied to part of your income.

Investment Tip: Consider working with a financial advisor or tax professional to compare the tax effects of withdrawals and Roth conversions across multiple years.

4. Estimate and Lock in Healthcare Coverage

If you’re retiring before age 65, you won’t generally be eligible for Medicare just yet. That makes healthcare one of the most urgent issues to address six months before retirement.

Suppose you’re 62 and planning to retire in January. You might compare options like COBRA from your employer, a plan from the Affordable Care Act marketplace or other coverage available to you. If you use a health savings account (HSA), Medicare enrollment also deserves attention because you generally cannot contribute to an HSA once Medicare coverage begins.

Investment Tip: Begin shopping early to compare costs, deductibles and provider networks. If you are approaching 65, review Medicare enrollment dates before leaving employer coverage. Medicare Part A can begin retroactively for up to six months when you enroll after 65, although coverage cannot begin before the month you turned 65. This can affect when you should stop making HSA contributions.

5. Decide When to Claim Social Security

Your Social Security claiming age has a major impact on your monthly benefit. While you can claim as early as age 62, delaying past your full retirement age (FRA), which is 67 for people reaching age 62 in 2026, can significantly increase your monthly check.

If your FRA is 67, claiming at 62 permanently reduces your benefit by about 30%. Waiting until age 70 permanently increases it by about 24% above your FRA amount.

Investment Tip: Factor in your life expectancy, spousal benefits and whether you plan to work part-time. If you claim before full retirement age while continuing to work, the Social Security earnings test may temporarily reduce your payments. In 2026, the earnings limit is $24,480 for someone under FRA for the entire year and $65,160 for earnings before reaching FRA during the year FRA is attained. Beginning with the month you reach FRA, earnings no longer reduce your benefits.

6. Update Estate Planning Documents

Your estate plan isn’t just about what happens after you’re gone. It also provides a clear framework for how your finances and healthcare choices will be managed if you lose the ability to make decisions.

At a minimum, review or create the following:

A will or trust
Financial power of attorney
Healthcare directive
Beneficiary designations

For example, a retiree who recently remarried may need to update beneficiaries to ensure assets pass to the intended spouse or children.

Investment Tip: Estate planning laws can vary by state. Consult with an estate planning attorney who can help you review whether your documents reflect your current wishes and comply with applicable state requirements.

7. Build a Retirement Paycheck Before Your Last Workday

Moving from a regular paycheck to retirement income can change when money reaches your bank account. Before leaving work, list the income you expect during your first year of retirement, including Social Security, pensions, annuities and planned portfolio withdrawals. Compare the monthly total with essential and discretionary expenses to identify any shortfall before your salary stops.

Timing is also important. Your final paycheck, unused vacation payout, bonus, pension payment and first Social Security deposit may arrive on different dates. Keeping enough cash available for several months of planned expenses can reduce the need to sell investments simply because a bill comes due during a market decline.

Review automatic payments and deposits as part of the transition. Employer benefits, payroll deductions and contributions to workplace retirement accounts may end with your last paycheck, while Medicare premiums, insurance costs or estimated tax payments can become new expenses. Mapping these changes onto a monthly budget can show how much you will actually need to withdraw from savings.

Investment Tip: Calculate how much monthly income your savings will need to provide after accounting for Social Security, pensions and other reliable income sources.

Bottom Line

Six months before retirement is when many people start taking final steps to organize their finances, investments, and benefits for the years ahead.

Six months before retirement is typically the time when you begin putting your plans into action. This period allows you to make final financial and healthcare decisions, such as adjusting investments, planning withdrawals or confirming your Social Security filing strategy. It also gives you time to review taxes, Medicare enrollment, estate documents and the transition from employment income to retirement withdrawals before your final paycheck.

“A pre-retirement checklist can help you spot weaknesses in your plan and give you time to make adjustments,” said Tanza Loudenback, a Certified Financial Planner™ (CFP®). “Recent tax legislation has introduced new rules around charitable giving, Roth conversions, senior deductions and more, so ask your financial advisor or tax professional to review your situation and model how these changes may affect your plan.”

Retirement Investing Tips

A financial advisor can help you build and manage a retirement investment strategy that balances growth, income and risk. Finding a financial advisor doesn’t have to be hard. SmartAsset’s free tool matches you with vetted financial advisors who serve your area, and you can have a free introductory call with your advisor matches to decide which one you feel is right for you. If you’re ready to find an advisor who can help you achieve your financial goals, get started now.
If you want to diversify your portfolio, here’s a roundup of 13 investments to consider.

Tanza Loudenback, a Certified Financial Planner™ (CFP®), provided the quotes used in this article. Please note that Tanza is not a participant in SmartAsset AMP, is not an employee of SmartAsset and has been compensated. The opinions voiced in the quote(s) are for general information only and are not intended to provide specific advice or recommendations.