The five years before retirement are usually less about finding one perfect number and more about making the important assumptions visible. You may be deciding when to leave work, how much the household will spend, when to claim Social Security, how to use retirement accounts, and how health care will fit into the plan. Each answer affects the others.
A retirement planning checklist gives those decisions an order. It helps you address the items with deadlines first, make room for the choices that need more thought, and avoid treating a single account balance as the whole story. Use this checklist to prepare for a conversation with the people and professionals who will help you make the decisions.
1. Define the retirement you want to support
Start with the life the money needs to support, not a generic benchmark. Consider when you and a spouse might stop working, whether part-time work could be useful, where you want to live, how often you expect to travel, the help you may want to offer family, and the activities that make retirement feel worthwhile. Then separate recurring needs from occasional wants. Housing, food, insurance, taxes, and health costs belong in the first group. Travel, home projects, gifts, and larger purchases can be planned separately so they do not disappear inside a monthly estimate.
Use recent bank and card statements to build the starting point. The goal is not to predict every dollar for the next 30 years. It is to identify the spending that is likely to continue, the costs that may end when work ends, and the expenses that could increase. A mortgage may be nearing payoff while health coverage, travel, support for family, or home maintenance could take on a larger role. MRA's budget planner can help organize the household numbers before a retirement projection turns them into income assumptions.
Retirement dates deserve the same care. Leaving at 62, 65, 67, or later can change the number of years the portfolio may need to provide income, the health insurance options available, and the timing of Social Security or pension choices. If you are a business owner, a succession timeline can add another layer. Write down at least two possible retirement dates, then ask what would need to be true for each one to feel realistic.
2. Build an income map before choosing withdrawals
List every source of income the household may have in retirement: Social Security, pension payments, part-time work, rental income, annuity income, cash reserves, taxable investments, traditional retirement accounts, Roth accounts, and any business-related proceeds. Then note when each source may begin and whether it is guaranteed, flexible, taxable, or tied to a decision you have not made yet.
Social Security is often a major part of this map. The Social Security Administration's retirement planning resources explain how to review your earnings record and compare benefit estimates. Do not look at just one claiming age. A benefit estimate at age 62, full retirement age, and age 70 can help show the tradeoff between starting sooner and creating a larger monthly benefit later. Couples should consider both records, especially where survivor income may matter.
If you have a pension, read the election options early. A larger payment that ends at the first spouse's death can create a very different household outcome than a smaller joint-and-survivor payment. If an employer offers a lump sum, obtain the plan documents and compare the choice with the income it would replace before making an election. The same rule applies to an annuity: confirm the payment terms, guarantees, inflation features, beneficiary provisions, and tax treatment rather than relying on a headline number.
Once income sources are listed, identify the annual gap between expected spending and dependable income. That gap is the job your savings and investments may need to do. MRA's retirement readiness review is built around this connected picture, helping households look beyond a balance and into the income, risk, tax, and timing choices behind it.
3. Review taxes before the final working years pass
Retirement changes more than a paycheck. The accounts you use, the timing of gains, a sale of company stock or a business interest, charitable gifts, and the age at which you begin benefits can all affect taxable income. The best time to review those questions is before a transaction or retirement date makes the options narrower.
Gather the last two tax returns and make a list of expected changes. That may include a final bonus, deferred compensation, stock compensation, severance, a pension election, the sale of a home, a business transition, or a move. Each item can have its own timing and tax implications. A withdrawal that looks reasonable on its own can become less attractive when added to other income in the same year.
Pay attention to required minimum distributions as well. Traditional retirement accounts can eventually require withdrawals, and the timing depends on the account owner and account type. The IRS maintains current required minimum distribution guidance, but personal planning should also account for the tax return, charitable goals, projected spending, and the people who may inherit the account.
Retirement-account contributions can still matter in the final working years, too. The IRS's retirement contribution guidance explains annual limits and catch-up rules, which can change. MRA's personal tax planning work can help bring the retirement-income question into the same conversation as the tax decisions already on your calendar.
4. Put health care and protection decisions on the calendar
Health coverage often has a deadline, which is why it belongs on a retirement checklist well before the final day of work. If retirement happens before Medicare eligibility, identify the coverage that will bridge the gap and the cost of that coverage. If Medicare is near, understand the enrollment timing, current employer coverage rules, prescription needs, providers, and the costs that may not be included in a plan premium.
Medicare's getting-started guide outlines enrollment and coverage basics. It is a useful place to begin, but the personal decision may also involve a working spouse's plan, retiree benefits, health savings accounts, income-related Medicare premiums, and the travel or provider access that matters to you. Put the dates and questions in writing instead of assuming a benefits deadline will be easy to revisit later.
Insurance deserves a wider review at the same time. Confirm health, life, disability, long-term care, home, auto, umbrella, and any business coverage that could change once work or income changes. Employer-provided life and disability coverage may end or change at retirement. MRA's umbrella insurance guide and Medicare and long-term care guide can help frame the questions, while the actual policy terms should guide the decision.
5. Adjust investments for the job they need to do
Approaching retirement does not automatically mean moving everything to cash. It does mean the portfolio may have a new job. Some money may be needed soon for spending, taxes, or a major purchase. Other money may need to support decades of future income. A useful review separates near-term needs from longer-term investments so a difficult market does not force the sale of assets meant to stay invested.
Start by identifying the amount needed over the next one to three years, then consider where that money will come from. Review concentrated positions, company stock, investment expenses, risk level, tax location, and whether the accounts you own still work together. MRA's investment risk review can help turn a broad concern about market movement into practical questions about time horizon, liquidity, and the role each account has in your plan.
Do not make a large allocation change solely because a retirement date is on the calendar. A decision that lowers short-term volatility can also reduce long-term growth potential, while a portfolio that ignores upcoming withdrawals can leave too little flexibility. The point is to make the tradeoff intentional. MRA's RetirementBuilder approach is designed to connect retirement-account investment decisions to the goals, risk, and timeline they are meant to support.
6. Confirm beneficiaries, documents, and the people who need to know
Retirement can expose records that have not been reviewed since a previous employer, a move, marriage, divorce, birth, death in the family, or a change in the size of the estate. Review retirement accounts, life insurance, annuities, bank accounts, transfer-on-death registrations, and workplace benefits for beneficiary designations. A will or trust can be important, but it does not necessarily replace an account or policy beneficiary form.
Confirm that your estate documents match the people and roles you would choose today. That can include a will, trust, powers of attorney, health care directive, and a current list of professional contacts. MRA's beneficiary guide and estate-planning resources can help organize the financial questions to bring to an attorney.
Make a simple, secure inventory of accounts, insurance policies, recurring bills, safe-deposit information, and important passwords or password-manager instructions. Tell the person who would need the information where to find it. The goal is not to hand someone a complicated binder. It is to make a stressful moment less confusing for the people you trust.
7. Use the final year as a rehearsal, not a scramble
During the final year before retirement, test the plan in real life. Try living on an expected retirement budget for a few months and direct the difference to savings. Confirm the health coverage transition, Social Security or pension application timing, account withdrawal process, tax withholding plan, and how the household will handle large irregular costs.
Schedule a review after the first few months of retirement, too. The transition can reveal spending patterns, tax questions, health coverage details, and investment needs that were difficult to see while working. A plan is more useful when it is revisited after real life supplies better information.
How MRA can help
MRA helps clients connect retirement income, investments, taxes, health care, insurance, estate planning, and family priorities in one practical conversation. That can be valuable when retirement is close enough to create deadlines but far enough away to preserve real choices.
If retirement is within the next five years, meet with an MRA advisor to start with the decisions that matter most to your household and the records that can help clarify them.
Frequently asked questions
What should I do five years before retirement?
Start by estimating the life your household wants retirement income to support. Then review expected spending, Social Security and pension choices, health coverage, taxes, account withdrawals, investment risk, beneficiaries, and the records you will need to make decisions. Five years is enough time to compare options and make changes gradually instead of reacting to a deadline.
How much money should I have before I retire?
There is no single dollar amount that fits every household. The more useful question is whether your expected income sources, savings, spending, taxes, health costs, and time horizon can support the retirement you want. A retirement projection can make those assumptions visible and help you test different retirement dates or spending choices.
When should I claim Social Security?
The right claiming age depends on your work plans, health, other income, taxes, marital situation, and the role Social Security will play in your household. Review your estimate at different claiming ages before deciding, especially when one spouse may have a different retirement date or a survivor benefit could matter later.
What documents should I organize before retirement?
Gather account statements, Social Security estimates, pension and workplace-benefit information, recent tax returns, insurance policies, beneficiary confirmations, estate documents, debt records, and a list of recurring bills. Keep the information in one secure place and update it after a move, job change, major purchase, or family change.
Related reading
This article is for general educational purposes and is not individualized tax, legal, investment, insurance, or financial advice. Retirement decisions, benefit choices, tax treatment, account withdrawals, and coverage rules depend on your personal circumstances. Review decisions with qualified professionals before acting.