The Retirement Readiness Checklist: 10 Things to Consider Before You Retire

Retirement is not simply the day your paycheck stops. It is the point when the financial life you have built must begin supporting the life you are about to enter.

For decades, the focus may have been on building: growing a career, leading a business, saving consistently, investing carefully, and providing for the people who depend on you. As retirement approaches, the work changes. The question is no longer only whether you have accumulated enough. It becomes whether your income, taxes, healthcare, investments, estate plan, and family responsibilities are all coordinated well enough to support the next season.

That transition can feel exciting, but it can also carry real weight. Many people arrive at retirement with multiple accounts, employer benefits, Social Security decisions, Medicare questions, aging parents, adult children, charitable goals, and a spouse who may or may not be equally involved in the financial details. The challenge is rarely a lack of discipline. More often, the challenge is bringing all the pieces into one clear plan.

The checklist below outlines 10 important areas to address before you retire. Each one gives you a chance to replace uncertainty with structure, so you can step into retirement with a plan that is thoughtful, flexible, and built around the life you actually want to live.

1. Define What Your Retirement Needs to Fund

Before you can know whether you are ready to retire, you need a clear picture of what retirement will require. That means looking beyond your regular monthly expenses and thinking carefully about the full life your plan needs to support.

Start with the essentials: housing, utilities, groceries, insurance, transportation, healthcare, and taxes. Then consider the lifestyle expenses that may become more important once you have more time available, such as travel, hobbies, club memberships, home projects, family visits, charitable giving, or time at a second property. Finally, account for larger expenses that do not arrive neatly every month, such as replacing a vehicle, helping a child or grandchild, repairing a roof, or navigating a medical event.

A useful retirement budget has three layers: what must be covered, what you want the freedom to enjoy, and what your plan needs to absorb when life is inconvenient or unexpected. Understanding these layers can give you a clearer picture of the kind of life your wealth is being asked to sustain.

2. Build a Plan for Replacing Your Paycheck

During your working years, income often arrives on a familiar schedule. Retirement changes that rhythm. Instead of one primary paycheck, your income may come from Social Security, pensions, retirement accounts, taxable investments, cash reserves, rental income, business-sale proceeds, deferred compensation, or other sources.

A retirement income plan should show where money will come from, how often it will be distributed, and how those distributions will be managed during both calm and difficult markets. It should also account for taxes, because a dollar withdrawn from a traditional IRA is not the same as a dollar withdrawn from a Roth IRA or a taxable brokerage account.

This is where many people feel the emotional shift of retirement most clearly. They may know how much they have saved, but they do not yet know how those savings will become dependable income. A well-built plan helps answer that question before the paycheck stops, so retirement feels less like a leap and more like a carefully prepared transition.

3. Create a Tax-Aware Withdrawal Strategy

The order in which you draw from your accounts can affect your tax bill, Medicare premiums, investment flexibility, and the longevity of your portfolio. Many retirees have a mix of traditional IRAs, 401(k)s, Roth accounts, taxable brokerage accounts, bank savings, and possibly employer stock or deferred compensation. Each account has its own tax treatment, and each should have a defined role.

Some retirees may benefit from using taxable assets first. Others may need retirement account withdrawals earlier than expected. In certain situations, the years between retirement and required minimum distributions can create a useful planning window for Roth conversions or other tax strategies.

Under current law, the age at which required minimum distributions begin depends on your birth year. The applicable starting age is generally 73 or 75, depending on when you were born. The first RMD can generally be delayed until April 1 of the following year, although doing so may result in two taxable RMDs in the same calendar year. Workplace retirement plans may have different timing depending on retirement status, ownership, and plan rules.

There is no single withdrawal order that works for every family. The better question is whether your accounts are being used in a way that supports your income needs, tax situation, estate goals, charitable intentions, and long-term flexibility.

4. Choose the Right Time to Claim Social Security

When to claim Social Security is one of the most important retirement income decisions because Social Security can provide lifetime income. Retirement benefits can generally begin as early as age 62, and the monthly benefit generally increases the longer you wait to claim, up until age 70.

That does not mean everyone should wait until 70, and it does not mean everyone should claim early. The right decision depends on factors such as your health, family longevity, spousal and survivor benefits, other income sources, tax picture, and whether you plan to keep working.

For married couples, Social Security should be considered as a household decision because one spouse’s claiming strategy may affect the financial security of the other spouse, particularly after the first spouse dies.

Rather than treating Social Security as a quick administrative step, coordinate it with the rest of your retirement income plan. The timing may affect how you manage taxes, withdrawals from other accounts, and long-term income for a surviving spouse.

5. Review Your 401(k) and Other Employer Benefits Before Retiring

Before you retire, take time to understand the role your employer-sponsored retirement plan will play. Some retirees leave assets in the plan, while others roll funds into an IRA. Some need immediate income, while others want to simplify account management or broaden investment options.

The right path depends on investment choices, costs, creditor protections, tax planning, distribution needs, and the level of coordination you want across your financial life.

The final working years may also offer an opportunity to increase retirement savings. For 2026, the annual employee contribution limit for 401(k), 403(b), governmental 457(b) plans, and the federal Thrift Savings Plan is $24,500. The general catch-up limit for many participants age 50 and older is $8,000, with a higher catch-up limit of $11,250 for eligible participants who turn age 60, 61, 62, or 63 during the calendar year.

Beginning in 2026, certain higher-earning participants may also be required to make catch-up contributions on a Roth basis, so it is important to understand how the rules apply to your employer’s plan.

This review should go beyond whether to roll over an account. Make sure your employer benefits, retirement accounts, stock positions, pension options, deferred compensation plans, and final-year savings opportunities are evaluated before you leave the workplace.

6. Make Sure Your Portfolio Is Prepared for Retirement

A portfolio designed to build wealth may not be the same portfolio you need when you begin drawing from it. During your working years, market volatility can feel uncomfortable, but you may still be adding to your accounts. In retirement, volatility can feel different because you may be withdrawing from the same portfolio that is moving up and down.

That does not mean a retirement portfolio should avoid risk altogether. Many retirees still need growth to help address inflation, longevity, and rising costs over time. The question is whether that risk is intentional, measured, and supported by a distribution strategy.

Before retirement, review whether your portfolio has enough liquidity for near-term needs, enough growth potential for the years ahead, and enough structure to help reduce the likelihood of selling long-term investments at an unfavorable time.

You cannot predict every market cycle. But you can build a retirement plan designed to continue functioning when markets are not cooperating.

7. Plan for Healthcare and Medicare

Healthcare is one of the most important planning areas in retirement, especially if you plan to retire before age 65. If there will be a gap between employer coverage and Medicare eligibility, understand how that gap will be covered and what it may cost. Options may include COBRA, a spouse’s plan, private coverage, or marketplace coverage, depending on your circumstances.

Medicare timing also deserves careful attention. Most people become eligible for Medicare at age 65. However, if you are covered by a qualifying employer group health plan based on your or your spouse’s current employment, you may be able to delay Medicare Part B and later qualify for a Special Enrollment Period.

For 2026, the standard monthly Medicare Part B premium is $202.90 and the annual Part B deductible is $283. Higher-income beneficiaries may also be subject to income-related monthly adjustment amounts.

Healthcare planning is not only about choosing coverage. It is also about understanding how income, taxes, premiums, and retirement distributions interact. A withdrawal strategy that looks efficient from an income tax standpoint may still affect Medicare costs, so these decisions should be reviewed together.

8. Prepare for the Possibility of Extended Care

Extended care is one of the harder topics to address because it involves more than numbers. It touches on independence, family roles, home, dignity, and the possibility that a spouse or adult child may one day need to make decisions during a stressful season.

A thoughtful plan should consider where you would want care to be provided, who would help coordinate it, how it would be funded, and how a care event could affect the rest of the family. Some families use traditional long-term care insurance. Others consider hybrid policies, self-funding strategies, or a combination of resources.

There is no perfect solution, but leaving the topic unaddressed can create more pressure later.

This is also a family communication issue. The people who may one day be involved should have some understanding of your preferences, legal documents, and financial resources. You do not need to burden them with every detail, but giving them direction now can keep them from having to guess when the stakes are high.

9. Revisit Your Estate Plan and Beneficiaries

Retirement is a natural time to revisit your estate plan. Wills, trusts, powers of attorney, healthcare directives, account titling, and beneficiary designations should all be reviewed before you enter this next season. Documents that made sense years ago may no longer reflect your family structure, assets, charitable goals, or wishes.

Beneficiary designations deserve special attention because they often control where retirement accounts, life insurance proceeds, annuities, and transfer-on-death accounts go. A will generally does not override beneficiary designations on these types of assets, which makes it important to review both your estate documents and the account-level details that sit alongside them.

For families with business interests, blended families, significant assets, charitable intentions, or adult children who may eventually share responsibility, estate planning should also include communication. A good plan does more than transfer assets. It can reduce uncertainty for the people who will one day need direction.

10. Make Sure Your Family Knows Where to Turn

Many people manage the majority of their household’s financial details themselves. They know where accounts are held, how bills are paid, which professionals to contact, where important documents are stored, and what needs attention. But if illness, incapacity, or death occurs, a spouse or adult child may suddenly be responsible for navigating those details during an already difficult time.

Preparing for retirement is an opportunity to make sure your family would know where to turn and what to do if you were no longer able to manage everything yourself. That means thinking beyond your investment accounts to the information that keeps your financial and household life running.

At GDS Wealth Management, we provide clients with a GDS Life Book, an organizational resource designed to bring important personal, financial, and household information together in one place. It provides a place to document key contacts, financial accounts, monthly expenses, insurance coverage, important documents, estate information, household details, legacy wishes, and other information your family may need. It also helps provide direction about whom to contact and what steps may need to be taken if something happens to you.

Completing and securely maintaining this information can give the people you love something invaluable: a place to start. Rather than leaving your family to piece together accounts, documents, contacts, and responsibilities during a difficult time, you can leave them with greater organization, direction, and clarity.

Retirement Readiness Is Built One Decision at a Time

Retirement confidence does not come from guessing, and it does not require having every answer at once. It comes from addressing important decisions before they become urgent.

When your income plan, withdrawal strategy, Social Security timing, healthcare coverage, investment approach, estate documents, and family communication are aligned, retirement can become easier to step into. There may still be uncertainty, but there is also structure. There may still be questions, but there is a process for answering them.

At GDS Wealth Management, our financial planning process is designed to coordinate income planning, tax planning considerations, benefits, Social Security, healthcare considerations, RMD planning, and legacy goals into a plan that evolves with your life.

If retirement is approaching, now is a good time to understand where you stand and identify the areas of your financial life that may need more attention.

Take our financial assessment to see how you’re tracking toward retirement and gain greater clarity about the road ahead. If you’re ready to speak with an advisor or review your financial plan with our team, please schedule a meeting. We look forward to serving you.