Retirement planning checklist

Key issues to address and steps to consider 10+ years, five years and one year before retirement.

Last updated October 15, 2025

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Like most significant life events, retirement planning has many stages. How you approach it at age 25 – when you may decide to open your first retirement account or participate in a company 401(k) – is very different from how to approach it at age 40, 50, or 60, when the amount of time left to reach your financial goals is limited. At each stage, there are specific guidelines and tasks that will help you get where you want to go. Wherever you are in the process, a retirement plan can put you in a better position to achieve financial confidence and retire comfortably.

If you’re still decades away from retirement, you should consider putting away a portion of every dollar you earn in a long-term tax-advantaged savings plan, for example by participating in your employer’s 401(k) or opening an Individual Retirement Account (IRA). The following checklist is meant for those getting closer to retirement age and outlines the key issues to address and steps to take– from reviewing your retirement account balances, to estimating your retirement income, to applying for Medicare and Social Security. If you’re age 40 or older, now might be a great time to make sure that your retirement plan is on track, find out what has to be done now, and plan ahead for what remains to be done in the coming years.

Checklist: 10+ years from retirement

If you’re 10 or more years from your expected retirement, the main focus of your checklist items should be making sure that you’re on track to building an adequate retirement fund. If not, you may need to adjust other expenses in your budget to prioritize retirement savings. Take it step-by-step and, if you run into any problems, think about consulting a professional financial professional for help.

Think about when and how you’d like to retire: At what age do you anticipate retiring? How many years do you have left to save and invest? What type of lifestyle do you want in retirement? Will maintaining the way you currently live cost more than you currently spend or will you “downsize” your lifestyle to reduce your expenses?
Estimate how much savings you’ll need in your retirement accounts: While this number is dependent on several factors — including when you retire and what kind of lifestyle you maintain — there are some retirement savings rules of thumb to make it easier. Many professionals advise accumulating 25 times your current annual expenses to ensure that you’ll make it through retirement without financial pressure – but many people retire with far less. Another common benchmark is to aim for retirement savings that will replace 70-80% of your pre-retirement income.
Review your retirement accounts and other assets to see if you’re on track: How close — or far — are you from your estimated retirement savings goal? Assess your current savings and compare it to your retirement goal to identify any gaps. If you continue to save at your current rate, will you reach your goal in time? If not, how much more should you contribute to your retirement accounts per year?
Review your investment strategy and results: Is your investment strategy generating the returns you need in order to reach your savings goals? Could you be earning more on your money without exceeding your risk tolerance? Asset allocation is crucial — consider diversifying your retirement investments across mutual funds and exchange traded funds to spread risk and simplify portfolio management. Take advantage of compound interest by investing early and consistently. And, if you’re not already working with an investment advisor, consider doing so: more than half (55%) of those who feel “exactly on track” for retirement work with a financial professional, versus just 20% of those who handle their finances independently.²
Will you be debt free by the time you retire? How much long-term debt — mortgage, college loans, medical bills — are you carrying? If you continue paying it down at your current rate, will you be debt free at retirement age? If not, can you find a way to allocate more money to accelerated repayment? Look at how much interest you’re paying on your debts to decide whether to prioritize repayment or invest for growth.
Are you prepared for increased health care and elder care costs? Medical expenses — including out-of-pocket costs — usually increase after retirement. Have you considered this possibility and worked it into your estimates of living expenses? Do you have Long Term Care Insurance?
Should life insurance be part of your plan? If you have a spouse or dependents who may still rely on you for financial support during retirement, should you consider life insurance? Will the savings in your retirement accounts be adequate for their needs, or would they need a death benefit as a supplement? Could tax-advantaged savings through a life insurance policy help you meet your goal?
Is now the time to purchase an annuity? Want to make sure you have enough money to cover your desired lifestyle long into retirement? While not appropriate for everyone, annuities can offer steady cash flow, and financial stability with the assurance you won’t outlive your retirement income. Plus, they often offer tax advantages, which can help to reduce tax burdens and maximize retirement savings.
Are you maximizing your retirement account options? If you do not have access to a workplace retirement plan, consider contributing to a traditional IRA, Roth IRA, or both. If you have a workplace plan, take advantage of any employer match to boost your savings.

Checklist: Five years from retirement

If you’re approximately five years away from your anticipated retirement age, it’s time to take a very close look at your finances, to think carefully about the details of your retirement plan, and to make some important decisions. And, if you feel overwhelmed or encounter unforeseen challenges, remember: there are professionals who can help.

Set a retirement date: You are now close enough to retirement to begin thinking about an actual date. While it doesn’t have to be a specific day or even a specific month, you should narrow the timeframe down enough so that you can accurately assess your finances and make sure that you will be prepared when retirement time comes.
Decide on a specific retirement location: In addition to having a specific idea about a retirement date, at this point you should also have specific ideas about where and how you plan to live when retired. Cost of living and access to amenities can affect your long-term financial security and quality of life. Will you stay in your current home, or will you move to a more or less expensive location? Do you plan to upgrade your lifestyle, or will you cut back in order to reduce living expenses? Having solid answers to questions like these is essential to figuring out if your retirement finances will be in order when you stop working.
Review retirement savings, assets and investments: With approximately five years left to save and invest, you want to be 100% certain that you’re on track to retire on or around your desired retirement date. Now is the time to total up all your resources — including IRAs, Roth IRAs, 401(k)s, non-retirement accounts, stock portfolios, and real estate — and determine whether you are close to your retirement savings goal. If you find a shortfall, be prepared to make some adjustments to your savings and investment strategy and/or to consider putting off retirement for a while longer than anticipated.
Transition out of high-risk investments: A widely accepted guideline surrounding retirement planning is that as you approach retirement age, you should reduce investment risk. Why? Because retirement is not a good time to weather a market downturn that might deplete your retirement fund for an extended period. Simply put, you want to know that your money will be there when you need it.
Decide when you will start taking Social Security benefits: As of 2025, you can begin collecting Social Security as early as age 62 and as late as age 70, with the monthly payment increasing the longer you wait. That said, the key question to ask yourself is at what age will you need the money to supplement other income? If the answer is age 62, the decision will be simple. However, if you can afford to put off collecting until full retirement age (age 67 as of 2025) or later, the calculation becomes more complicated. The timing of your claim will directly affect the social security benefit you receive, so consider your options carefully. For instance, you’ll have to figure out if it makes sense to start earlier and collect a lower monthly amount for more years, or to delay as long as possible and collect a higher monthly amount for less years? You should do some research before making any final decisions and, if necessary, consult a financial professional for help.
Familiarize yourself with Medicare: While full retirement age has been raised to 67, Medicare coverage is still available at age 65. So, as you approach that birthday, you’ll want to start getting familiar with your options. Keep in mind that when you reach enrollment age, you’ll be asked to choose between traditional Medicare (the government program) and Medicare Advantage (administered by private insurers). It’s an important decision, so you won’t want to leave it until the last minute.

Checklist: One year from retirement

At one year from retirement, it will be time to take care of the “nuts-and-bolts” involved in the transition from your working years to your retirement years. Some of these tasks must be completed by a specified date, so please make sure you have accurate information and keep an eye on your calendar.

Apply for Social Security benefits: If you’ve yet to apply for Social Security — and want to begin collecting as soon as you stop working — don’t wait until the last minute. The sooner you apply, the sooner your payments will begin. You can apply online, by phone, or in person at your local Social Security office. Required documentation will include your Social Security number, birth certificate, and proof of U.S. citizenship or lawful immigration status.
Apply for Medicare: If you are planning to enroll in traditional Medicare (the government program), you can apply beginning three months before your 65th birthday and up until three months after.³ If you miss this window and then decide to apply, you’ll have to pay a late enrollment penalty that will increase your monthly premiums. To apply, visit the official Social Security Administration (SSA) website or call their toll-free number. If you prefer, you can visit your local SSA office in person.
Or, apply for Medicare Advantage: If you are interested in Medicare Advantage — an alternative to Medicare offered by private health insurance companies — plan to spend some time researching and comparing the many different plans offered in your area. You may want to enlist the help of an insurance broker who can help you to evaluate the plans and make the best possible decision.
Transition insurance away from your workplace: At some point before retiring, inquire about your employee health insurance plan and whether coverage of any kind is available after retiring. If yes, decide whether it makes sense to take advantage of the benefit as a supplement to your Medicare or Medicare Advantage. Whether or not your employer offers ongoing coverage, make sure that your HR department is aware of your retirement date, and the date on which your Medicare or Medicare Advantage coverage will begin. This will help to ensure that there are no gaps in your health insurance coverage.
Develop a drawdown plan: A strategy for withdrawing funds — i.e., turning your built up savings into monthly income to live on — is a crucial piece of the retirement planning puzzle. An effective drawdown plan must reflect several factors, including your estimated lifespan, anticipated expenses, required minimum distributions, and inflation. It should also reflect your sources of income — including Social Security, pension or retirement accounts, and investments — and strike a balance between covering expenses and preserving principal. When withdrawing from accounts like traditional and Roth IRAs, ensure that your withdrawals are qualified withdrawals that benefit from tax-advantaged treatment. You may wish to consult with a tax professional for guidance on the tax implications of your withdrawals and to ensure proper tax documentation. With a thoughtful drawdown plan, individuals can navigate their retirement years with confidence and financial stability.

Resources to help with your retirement plan

While 77% of US adults say they strive to live comfortably in retirement, according to recent Guardian research, only 32% say they’re good at setting up and sticking to a long-term financial strategy.¹ The good news is, there are a many resources available to help you make the most of your finances in retirement

Social Security Resources

As you start thinking about when and how to apply for Social Security, you’ll probably have a lot of questions. These resources can help you navigate the process:

Social Security Administration (SSA) Website: The official website of the SSA — www.ssa.gov — provides detailed information about Social Security benefits, eligibility criteria, application procedures, and various tools and calculators to estimate benefits.
Online Benefit Planner: The SSA's Benefit Planner offers interactive tools like the Retirement Estimator and the Benefits Calculators.
Social Security Publications: The SSA publishes informative brochures, fact sheets, and guides on various topics related to Social Security. You can access these publications on the SSA website or request physical copies to be mailed to you.
Local Social Security Office: If you prefer in-person assistance, you can visit your nearest Social Security office. The SSA's website provides a search tool to find the office closest to your location.
Social Security Toll-Free Number: You can contact the SSA by phone through their toll-free number, 1-800-772-1213 (TTY 1-800-325-0778). Representatives are available to answer questions, provide information, and assist with the application process.
Online Application: The SSA allows you to apply for Social Security benefits online. The application is available on their website, and it guides you through the process step-by-step.
Social Security Statement: You can request a personalized Social Security Statement that provides an estimate of your future Social Security benefits. The statement also includes a record of your reported earnings history, which is crucial for determining benefit amounts.

Medicare Resources

There are a number of specific rules and deadlines to consider as you prepare to apply for Medicare or a Medicare Advantage plan. Here are some key resources you can use for help:

Official Medicare Website: The official website of Medicare, www.medicare.gov, is an excellent resource for all things related to Medicare. It provides comprehensive information on eligibility, enrollment periods, coverage options, and how to apply.
1-800-MEDICARE Helpline: You can call the 1-800-MEDICARE helpline (1-800-633-4227) to speak with a representative who can answer your questions, provide assistance with enrollment, and guide you through the application process. The helpline is available 24 hours a day, seven days a week.
Medicare & You Handbook: Medicare publishes an annual handbook called "Medicare & You," which provides detailed information about Medicare coverage, costs, and enrollment. You can access the handbook online on the official Medicare website or request a printed copy to be mailed to you.
State Health Insurance Assistance Programs (SHIP): SHIP is a network of state-based programs that offer free counseling and assistance to Medicare beneficiaries. They provide personalized guidance on Medicare options, help with enrollment, and answer questions about coverage. To find your local SHIP office, visit the official Medicare website or call 1-800-MEDICARE.
Medicare Advantage Plan Finder: If you're considering enrolling in a Medicare Advantage plan, you can use the Medicare Plan Finder tool on the official Medicare website. It allows you to compare different Medicare Advantage plans available in your area, including their costs, coverage, and quality ratings.
Local Insurance Agents and Brokers: Insurance agents and brokers who specialize in Medicare can offer personalized assistance in understanding your options and choosing the right plan. They can help you navigate the enrollment process and provide guidance based on your specific needs and preferences.

Guardian can be a resource, too

The checklist above can be a valuable tool in preparing for retirement and can help you to develop your retirement strategy. However, as you get deeper into the planning process, there may be financial issues and questions that require you to consult a financial professional with retirement planning experience.

If you don’t currently have a financial professional, we can help. A Guardian Financial Professional will listen to your needs, help define your goals, and work with you to better understand the retirement planning process and help make the appropriate decisions.

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Frequently asked questions about retirement planning

Start by using one of the checklists in this article, or you can download many similar lists from the internet. You may have to do some customization to reflect your specific retirement and financial planning needs, but most are fairly comprehensive. Once you have a list that fits your needs, set aside some time to consider each item and take any actions needed to address them. And if you feel you need help, don't hesitate to consult a financial professional.

The “5-retirement rule” was once a popular guideline that suggested withdrawing no more than 5% of your retirement savings each year in order to preserve your retirement savings. Nowadays, however, financial professionals are more likely to suggest limiting withdrawals to 4% per year in order to ensure long-term sustainability while accounting for inflation and potential market fluctuations. This approach promotes a balanced withdrawal rate, designed to help retirees maintain a steady income stream throughout retirement, while also safeguarding their assets for unexpected expenses and above average longevity.

This material is intended for general public use. By providing this content, The Guardian Life Insurance Company of America, and their affiliates and subsidiaries are not undertaking to provide advice or recommendations for any specific individual or situation, or to otherwise act in a fiduciary capacity. Please contact a financial representative for guidance and information that is specific to your individual situation. All investments contain risk and may lose value. Diversification does not guarantee profit or protect against market loss. Guardian, its subsidiaries, agents, and employees do not provide tax, legal, or accounting advice. Consult your tax, legal, or accounting professional regarding your individual situation. The Social Security Administration and Centers for Medicare and Medicaid Services have not approved, endorsed, or authorized this material. Contact them directly for complete details regarding eligibility and benefits. Links to external sites are provided for your convenience in locating related information and services. Guardian, its subsidiaries, agents and employees expressly disclaim any responsibility for and do not maintain, control, recommend, or endorse third-party sites, organizations, products, or services and make no representation as to the completeness, suitability, or quality thereof.

1 Mind, Body, and Wallet® 2025, The Guardian Life Insurance Company of America, 2025.

2 When to sign up for Medicare, Social Security Administration.

3 Mind, Body, and Wallet® 2025, The Guardian Life Insurance Company of America, 2025.

Retirement planning checklist

Checklist: 10+ years from retirement

Checklist: Five years from retirement

Checklist: One year from retirement

Resources to help with your retirement plan

Social Security Resources

Medicare Resources

Guardian can be a resource, too

Need some help?

Need more retirement planning information?

Retirement planner

Retirement plan

Retirement income planning

Frequently asked questions about retirement planning

How do I prepare a retirement checklist?

What is the 5-retirement rule?

Disclaimer8491376.1•Exp 10/27angle down

Checklist: 10+ years from retirement

Checklist: Five years from retirement

Checklist: One year from retirement

Resources to help with your retirement plan

Social Security Resources

Medicare Resources

Guardian can be a resource, too

Frequently asked questions about retirement planning