Presented by Axial Financial Group. 

Retirement is an exciting milestone, but preparing for it involves more than choosing your final day of work. The decisions you make during the years leading up to retirement can affect your income, taxes, healthcare, and overall financial flexibility.

Whether retirement is several years away or just around the corner, this checklist can help you identify important questions to discuss with your Axial advisor, or your tax, and legal professionals.

1. Define What Retirement Looks Like to You

Before focusing on the numbers, think about how you would like to spend your time.

Consider:

• Where you plan to live
• Whether you hope to travel
• If you intend to work part-time or volunteer
• How you will spend your day-to-day life
• Whether you expect to provide financial support to family members

 

Having a clearer picture of your retirement lifestyle can help you create a more realistic financial plan.

2. Estimate Your Retirement Expenses

Review your current spending and consider which expenses may increase, decrease, or disappear in retirement.

Your retirement budget should account for:

• Housing and home maintenance
• Healthcare and insurance
• Food and transportation
• Travel and entertainment
• Taxes
• Family support or gifting
• Unexpected expenses

 

It may also be helpful to separate essential expenses from discretionary spending. This can show you where you may have flexibility during periods of market volatility or unexpected change.

3. Take Inventory of Your Income Sources

Make a list of the income you expect to receive throughout retirement, including:

• Social Security
• Pensions
• Retirement accounts
• Investment accounts
• Annuities
• Rental or business income
• Part-time employment

 

The next step is determining when each income source should begin and how they can work together to support your spending needs.

4. Review Your Social Security Options

The age at which you claim Social Security can affect the amount of your monthly benefit. Benefits may generally begin as early as age 62, but the right timing depends on your health, life expectancy, marital status, other income sources, and broader retirement plan.

Review your estimated benefit through your my Social Security account and consider how different claiming ages may affect both you and your spouse. The Social Security Administration allows individuals to apply up to four months before they want their benefits to begin. Learn more from the Social Security Administration.

5. Create a Healthcare Plan

Healthcare is one of the most important (and sometimes underestimated) retirement expenses.

If you plan to retire before age 65, determine how you will maintain coverage until becoming eligible for Medicare. Options could include coverage through a spouse, COBRA, a former employer, or the Health Insurance Marketplace.

If you are approaching age 65, learn when and how you need to enroll in Medicare. The initial enrollment period generally lasts seven months, beginning three months before the month you turn 65 and ending three months afterward. Enrollment requirements can vary if you or your spouse are still covered by an employer plan. Missing the appropriate enrollment window may result in a coverage gap or late-enrollment penalty. Review Medicare enrollment information.

6. Evaluate Your Retirement Savings

Review your retirement accounts and assess whether your current savings pace remains aligned with your goals.

Questions to consider include:

• Are you taking full advantage of an employer match?
• Can you increase contributions during your final working years?
• Are catch-up contributions available to you?
• Is your investment allocation appropriate for your timeline?
• Do you have enough accessible savings outside your retirement accounts?

 

For 2026, eligible employees can generally contribute up to $24,500 to a 401(k), 403(b), or governmental 457 plan, plus an $8,000 catch-up contribution for those age 50 or older. Different rules and enhanced catch-up limits may apply in certain situations. View current contribution limits from the IRS.

7. Develop a Retirement Withdrawal Strategy

Retirement requires a shift from saving money to determining how and when to use it.

A thoughtful withdrawal strategy should consider:

• Which accounts to draw from first
• How much to keep in cash
• How withdrawals may affect your taxes
• How to generate reliable income
• How to respond during market downturns
• When required minimum distributions may begin

 

Required minimum distributions generally begin at age 73 under current law, although individual circumstances and account types can affect the rules. Read the IRS guidance on RMDs.

8. Review Your Tax Strategy

Your tax situation may change significantly once your paycheck stops. Some retirement income may be taxable, and withdrawals can also affect Medicare premiums and the taxation of Social Security benefits.

Before retiring, consider discussing:

• Traditional versus Roth account withdrawals
• Potential Roth conversions
• Capital gains and losses
• Charitable giving strategies
• Pension and Social Security taxation
• Required minimum distributions
• Your state of residence in retirement

 

Tax planning should ideally happen before retirement, while you may still have time to adjust your income and savings strategy.

9. Pay Down Debt and Strengthen Your Cash Reserve

Review your mortgage, credit cards, auto loans, and other outstanding debts. Retiring debt-free can reduce monthly expenses, but using a large portion of your savings to eliminate a low-interest loan may not always be the right decision.

It is also important to maintain an emergency reserve for home repairs, medical costs, and other unexpected expenses. The appropriate amount will depend on your anticipated spending, income sources, and comfort level.

10. Update Your Estate Plan and Beneficiaries

Make sure your estate documents continue to reflect your wishes.

Review your:

• Will
• Trust documents, if applicable
• Financial and healthcare powers of attorney
• Healthcare directive
• Retirement account beneficiaries
• Life insurance beneficiaries
• Transfer-on-death designations

 

Beneficiary designations generally determine how certain accounts are distributed, so they should be reviewed after major life events such as marriage, divorce, a birth, or a death in the family.

One Final Step: Test Your Retirement Plan

Before giving notice at work, consider living on your projected retirement budget for several months. This trial run can help you determine whether the budget feels comfortable and identify expenses you may have overlooked.

Retirement planning is not about predicting every detail perfectly. It is about creating a strategy that can adapt as your life, priorities, markets, and tax laws change.

If retirement is approaching, now may be a good time to review your income plan, investment strategy, healthcare coverage, and long-term goals with your financial advisor.

Want to prepare as best you can before or during your discussion with your Axial advisor?

Here is a printable Pre-Retirement Checklist to get you started!

Axial Financial Group. All Rights reserved. 1 Van de Graaff Drive, Suite 500, Burlington, Massachusetts. 781.273.1400

This material is intended for general informational purposes only and should not be considered individualized investment, tax, or legal advice. Before making any tax-related decisions, consult with your financial advisor and tax professional. This article was developed with the assistance of generative artificial intelligence and reviewed, edited, and verified by the author/advisor prior to publication.