10 Things to Do Before You Retire: A Checklist

10 Things to Do Before You Retire: The Essential List

Eric Bilitz | Feb 19, 2026

Key Takeaways

Establish your financial baseline: A strong retirement plan is built on knowing your current financial health. Take inventory by calculating your net worth, creating a debt payoff strategy, and ensuring your legal paperwork is up to date.
Design your retirement "paycheck": Thoughtfully plan how you'll fund your life after work. This involves maximizing your Social Security benefits, creating a sustainable withdrawal strategy from your savings, and budgeting for future expenses like healthcare.
Partner with the right experts: Retirement planning is a team sport, so you don't have to go it alone. A financial advisor, tax professional, and attorney can provide specialized guidance, ensuring your financial and legal plans work in harmony.

Get a Clear View of Your Finances

Before you can map out your retirement, you need to know your starting point. Getting a clear, honest look at your finances is the first and most important step. It’s about moving past guesswork and building a solid foundation for your future. This process gives you the information you need to make smart decisions, whether you’re five or twenty years from retirement. Let's break down how to get that clear view.

Calculate Your Net Worth

Your net worth is a simple yet powerful number: what you own (assets) minus what you owe (liabilities). To figure it out, make two lists. For assets, include cash, your home's current value, and investment portfolios. For liabilities, list your mortgage, car loans, and credit card debt. Subtract your total liabilities from your total assets to get your net worth. This figure gives you a realistic baseline of the resources you have to fund your retirement. You can use online financial calculators to help with the math and get a clear snapshot of your financial health.

Review All Your Income Sources

When you retire, your regular paycheck stops, but your income doesn't have to. Your retirement income will likely come from several places. List every potential source: Social Security, pensions, 401(k)s, IRAs, and any rental or investment income. For each one, learn the rules. When can you start taking withdrawals? How much can you expect each month? And how will that income be taxed? Understanding the mechanics of each stream is essential for creating reliable cash flow. A comprehensive financial planning process helps organize these sources into a cohesive strategy for your future.

Check In on Your Retirement Savings

Your total retirement savings balance doesn’t tell the whole story. You need to project how long that money will actually last, considering factors like inflation, healthcare costs, and taxes on withdrawals. Think about your savings in terms of the annual income it can generate. Will your nest egg support the lifestyle you envision for 20, 30, or even 40 years? This is where professional guidance on asset management becomes invaluable. An advisor can help you stress-test your portfolio and ensure your savings are aligned with your long-term retirement goals.

Create a Plan to Tackle Debt

Entering retirement with a clean slate is one of the best gifts you can give your future self. Debt, especially the high-interest kind, can act as an anchor, weighing down your savings and adding unnecessary stress to what should be a relaxing chapter of your life. Imagine your retirement income not having to be split between living expenses and old credit card bills or loans. That freedom is entirely possible with a solid plan.

Creating a strategy to pay down what you owe is a critical part of financial planning. It’s not just about making payments; it’s about making the right payments. By looking at all your debts together, you can decide which ones to prioritize and how to allocate your resources most effectively. This proactive approach ensures your hard-earned retirement savings can be used for what they were intended for: supporting your lifestyle, pursuing hobbies, and enjoying your time without the constant worry of monthly debt payments. Getting organized now will make your transition into retirement much smoother and more secure.

Focus on High-Interest Debt First

When you have multiple debts, it can be tough to know where to start. The most effective strategy is often to target your high-interest debts first. Think credit cards, personal loans, or any other debt with a double-digit interest rate. These are the most expensive debts because they accumulate interest quickly, making them harder to pay off over time.

By funneling any extra money toward the balance with the highest interest rate while making minimum payments on the others, you’ll save a significant amount of money in the long run. As one source puts it, "Try to pay off all your debts, especially high-interest ones, before you retire. This gives you peace of mind." Use one of our financial calculators to see how much you could save.

Explore Debt Consolidation

If you're juggling several different payments each month, debt consolidation might be a great option to simplify your financial life. This process involves taking out a new, single loan to pay off multiple existing debts. The goal is to secure a lower interest rate than what you’re currently paying across all your different accounts. This can make your debt more manageable and potentially help you pay it off faster.

Consolidating your debts means you’ll only have one monthly payment to keep track of, which reduces the risk of missing a due date. Paying off high-interest debts like credit cards before you retire can make your savings last longer. Understanding if this is the right move for you is a key part of our process when we work with clients to build their retirement roadmap.

Map Out Your Mortgage Payoff

The question of whether to pay off your mortgage before retiring is a common one, and the answer isn't always straightforward. For many, the idea of owning their home outright provides incredible peace of mind. However, from a purely financial standpoint, it might not always be the best move to prioritize it over other goals.

If your mortgage has a low interest rate, it could be more beneficial to direct extra funds toward higher-interest debt or even your investment accounts. As one expert notes, "You can pay off your home mortgage last if it has a low interest rate." The right choice depends on your personal risk tolerance, the terms of your loan, and your overall financial plan. It’s worth weighing the emotional benefits against the mathematical ones.

Make the Most of Your Social Security

Social Security is a key piece of most retirement income plans, so it pays to be strategic. The decisions you make about when to claim your benefits can have a lasting impact on your financial comfort for years to come. It’s not just about waiting for a check; it’s about actively managing this asset. Let's walk through three essential steps to ensure you're maximizing your benefits.

Know Your Full Retirement Age

Your first step is understanding your "full retirement age," or FRA. This is the age you're entitled to 100% of the Social Security benefits you've earned, and it varies based on your birth year. While you can start claiming at 62, doing so permanently reduces your monthly payment. Your benefit is calculated from your 35 highest-earning years, so knowing your specific full retirement age provides a crucial baseline for planning. It helps you decide when to start collecting payments and map out your retirement timeline more effectively.

See How Delaying Benefits Affects You

Patience can pay off when it comes to Social Security. If you can wait past your full retirement age to claim benefits, your monthly payment will increase for every year you delay, up to age 70. For many, waiting until 70 could result in a monthly payment that's over 30% higher than what they would have received at their FRA. This decision depends on your personal situation, including your health, other savings, and income needs. It's a good idea to run the numbers to see how different claiming ages would impact your overall retirement income and fit into your financial plan.

Check Your Earnings History for Errors

Your Social Security benefit is tied directly to your lifetime earnings record, so accuracy is essential. The Social Security Administration (SSA) tracks your earnings, but mistakes can happen, and an incorrect year of income could lower your benefit for life. You can easily review your earnings statement by creating a free account on the SSA's website. Take a few minutes to look over your history and compare it with your own records. If you spot a discrepancy, you can request a correction. This simple checkup is one of the easiest ways to protect your future retirement income.

Plan for Healthcare and Long-Term Care

Healthcare is one of the most significant expenses you’ll face in retirement, and it’s often the hardest to predict. As you get older, your medical needs will likely change, and it’s important to have a plan in place to handle those costs without derailing your financial security. Thinking through your options for health insurance, potential long-term care needs, and out-of-pocket expenses is a critical piece of your overall financial plan. By addressing these topics before you retire, you can move into your next chapter with more confidence and peace of mind.

Research Your Medicare Options

As you approach age 65, you’ll need to get familiar with Medicare. This isn’t something you want to put off, as your initial enrollment period is time-sensitive, and missing it can lead to lifelong penalties. Medicare is the federal health insurance program for seniors, but it’s not a one-size-fits-all solution. It’s broken into different parts that cover hospital stays, doctor visits, and prescription drugs. You’ll have to decide between Original Medicare, often paired with a Medigap policy, or a Medicare Advantage plan. You can start by exploring the official Medicare website to understand the basics and see what makes the most sense for your health needs and budget.

Decide if You Need Long-Term Care Insurance

One common misconception is that Medicare will cover extended stays in a nursing home or the cost of a home health aide. For the most part, it doesn’t. Long-term care helps with daily activities like eating, bathing, and dressing, and these services can be incredibly expensive. Without a plan, you could end up depleting your retirement savings quickly. Long-term care insurance is one way to protect your assets. When deciding if it’s right for you, consider your family’s health history and your personal wishes for care. This is a complex decision, and it’s a good idea to discuss it as part of your broader wealth management strategy.

Budget for Out-of-Pocket Health Costs

Even with great insurance coverage, you’ll still have out-of-pocket healthcare costs in retirement. These include premiums, deductibles, copayments, and expenses for services that Medicare typically doesn’t cover, like routine dental, vision, and hearing care. It’s smart to get any major check-ups or medical procedures done while you’re still covered by your employer’s health plan. As you build your retirement budget, be sure to include a dedicated line item for these ongoing health expenses. If you have a Health Savings Account (HSA), it can be an excellent, tax-advantaged way to pay for these costs. Planning ahead ensures these expenses are manageable and don’t become a source of stress.

Plan Your Retirement Account Withdrawals

You’ve spent decades saving for retirement, and now it’s time to think about how you’ll use that money. Creating a smart withdrawal strategy is just as important as your savings plan was. How and when you take money out of your accounts can have a big impact on how long your savings last and how much you pay in taxes. A thoughtful approach ensures you can enjoy your retirement without worrying about outliving your funds. Planning your withdrawals helps you create a steady, predictable income stream that supports the lifestyle you’ve worked so hard to build.

Strategize Your 401(k) and IRA Withdrawals

When you pull money from traditional retirement accounts like a 401(k) or IRA, that money is typically taxed as ordinary income. This means your withdrawal strategy is also a tax strategy. Instead of taking out large, random sums, it’s often better to plan your withdrawals to keep your taxable income as low as possible. Think about which accounts to draw from first and how much you need each year to cover your expenses. A well-designed financial plan can help you map this out, creating a "paycheck" for yourself in retirement that balances your needs with tax efficiency.

Understand Required Minimum Distributions (RMDs)

The IRS requires you to start taking withdrawals from most retirement accounts once you reach a certain age. These are called Required Minimum Distributions, or RMDs. The government wants to get the tax revenue from your tax-deferred savings, and RMDs are how they ensure it happens. The starting age for RMDs can change, so it's important to stay up-to-date on the current rules. Failing to take your full RMD on time can result in a steep penalty. You can use an online RMD calculator to get an estimate of what you’ll need to withdraw each year, which is a great first step in planning your income.

Look into Roth Conversions

A Roth conversion is a strategy where you move funds from a traditional, pre-tax retirement account into a post-tax Roth IRA. You’ll have to pay income tax on the amount you convert in the year you do it. So, why would you do this? The main benefit is that once the money is in the Roth IRA, all future qualified withdrawals are completely tax-free. This can be a powerful move if you expect to be in a higher tax bracket in the future or if you want to reduce your RMDs down the road (Roth IRAs don't have them). It’s a complex decision, so it’s wise to discuss your options with a financial advisor to see if it fits your wealth planning goals.

Get Your Legal Documents in Order

While finances are often top of mind for retirement, getting your legal house in order is just as important. Up-to-date legal documents ensure your wishes for your assets and health are clearly defined and protected. This isn't just about planning for the inevitable; it's about giving yourself and your loved ones peace of mind. When these documents are current, you remove ambiguity and potential stress for your family down the road. Taking the time now to review your will, healthcare directives, and beneficiaries means your intentions will be honored.

Review Your Will and Estate Plan

Your life isn't static, and your will shouldn't be either. Major life events like marriages, births, or even significant financial changes can make an old will obsolete. Pull out your will and other estate planning documents, like your power of attorney, and read through them carefully. Do they still reflect who you want to inherit your assets and who you trust to manage your affairs? A comprehensive financial planning process includes making sure these documents align with your current goals. If anything seems off, it’s time to connect with an attorney to make updates.

Update Your Healthcare Directives

What happens if you can't make medical decisions for yourself? This is where healthcare directives, such as a living will and a healthcare power of attorney, come into play. These documents outline your wishes for medical treatment and appoint someone you trust to make decisions on your behalf. As you approach retirement, it's a good time to review these instructions. Make sure your designated healthcare agent is still the right person for the job and that they understand your wishes. This simple step gives you a voice in your own healthcare, no matter what the future holds.

Check Your Beneficiaries

This is one of the most critical and frequently overlooked tasks. The beneficiary designations on your retirement accounts (like your 401(k) and IRA) and life insurance policies directly determine who receives that money, and they override what’s written in your will. An outdated beneficiary, like an ex-spouse, could inherit your assets if you haven't updated the forms. Log into each of your accounts and confirm that the listed beneficiaries are correct. Proper asset management involves ensuring your wealth is transferred exactly as you intend.

Picture Your Ideal Retirement Lifestyle

Retirement planning often gets bogged down in numbers, but the numbers only matter if they support the life you want to live. Before you can build a realistic budget, you need a clear vision of what your retirement will actually look like. What will you do with all that newfound free time? Thinking about this now makes the financial side of planning much more tangible and exciting. It’s not just about saving money; it’s about funding your future.

This is your chance to dream a little. Do you see yourself traveling the world, or are you more of a homebody who wants to perfect your garden and spend more time with grandkids? Maybe you want to start a passion project, volunteer for a cause you care about, or even work part-time in a field you love. Having a clear picture of your goals helps you and your financial team create a financial plan that truly fits your aspirations. The clearer your vision, the easier it is to map out the financial steps to get there.

Define Your Retirement Goals

A great way to think about this is to plan what you want to retire to, not just what you’re retiring from. Leaving your nine-to-five is the end of one chapter, but it’s the beginning of a brand new one that you get to write. What activities, hobbies, and interests will fill your days? Make a list of everything you’d like to do, from big adventures like hiking a national park to simple pleasures like reading on the porch. This isn’t just daydreaming; it’s the essential first step in designing a retirement that feels fulfilling and purposeful.

Estimate Your Monthly Expenses

Once you have a vision, you can start putting some numbers to it. Your spending habits will likely change in retirement. Some costs, like commuting and work lunches, might disappear, but others, like travel and healthcare, could increase. The best way to get a handle on this is to track your current spending for a few months. This gives you a realistic baseline. From there, you can adjust for your new lifestyle. A great strategy is to try living on your projected retirement budget for a month or two before you actually retire. It’s a practical test run to see if your estimates are on track.

Think About Where You'll Live

Your home is one of your biggest assets and expenses, so deciding where you’ll live is a major piece of the retirement puzzle. Will your current home suit your needs as you age, or does downsizing make more sense? Perhaps you’ve always dreamed of moving closer to family or relocating to a warmer climate. When considering a move, think beyond just the cost of living. Consider your social network, access to quality healthcare, and proximity to the activities you want to enjoy. If you’re thinking about a new city, try renting there for a few months first to see if it’s a good fit before making a permanent move.

Create Additional Income Streams

Relying on a single source of income in retirement can feel restrictive. Creating multiple income streams before you stop working builds a more resilient financial future, giving you flexibility and peace of mind. Think of it as building a safety net. If one income source fluctuates, like the stock market, you have others to lean on. This approach can help you cover your essential expenses while leaving more room for the activities you’ve been looking forward to, whether that’s traveling, pursuing hobbies, or spoiling your grandkids. It’s about creating options so you can live your retirement on your own terms, not just getting by. The years leading up to retirement are the perfect time to explore these possibilities. You still have your primary income to support you as you experiment with a side business, invest in a rental property, or build a dividend-focused portfolio. By the time you're ready to leave the workforce, these supplemental streams can be well-established, providing a reliable flow of cash to complement your retirement savings and Social Security. This strategy helps protect your nest egg from being depleted too quickly and gives you the confidence to truly enjoy your post-career life.

Explore Passive Income Ideas

Passive income is money you earn without actively working for it every day. Setting up these streams takes effort upfront, but the goal is to have them generate cash flow with minimal ongoing work. Common examples include rental income from a property, dividends from stocks, or interest from bonds and high-yield savings accounts. Building a portfolio that provides steady asset management income is a popular strategy for retirees. The key is to start planning and building these income sources while you’re still working, so they are mature and reliable by the time you need them.

Consider Part-Time Work

Retirement doesn’t have to mean a complete stop to working. For many, part-time work provides a perfect transition. It offers extra income, a sense of routine, and valuable social interaction. You could leverage your decades of experience by consulting in your field or mentoring younger professionals. If you’re a small business owner, you might consider scaling back your hours instead of selling the company entirely. This can be a great way to keep your mind sharp and your wallet full. Or, you could turn a lifelong hobby into a small side business, doing something you truly love on a flexible schedule.

Evaluate Your Investment Income

Your retirement accounts are more than just a lump sum of savings; they are a potential source of regular income. Before you retire, it’s crucial to evaluate how your investments will translate into a steady paycheck. Understand how each income stream works, how much you can sustainably withdraw each month, and the tax implications of those withdrawals. Your investment income might come from dividends, bond interest, or by selling assets. Creating a cohesive financial planning strategy around these sources is essential to make your money last. It’s always a good idea to talk to a financial professional about this to ensure your plan is tax-efficient.

Build Your Retirement Budget

Once you have a clear picture of your ideal retirement, it’s time to build a budget that can make it happen. Think of this budget less as a set of restrictions and more as a roadmap for your spending. It helps you align your financial reality with your retirement dreams. A solid budget is built on a few key pillars: a smart withdrawal plan, a strategy for economic changes, and a safety net for life’s surprises.

Create a Sustainable Withdrawal Plan

Your retirement savings are meant to support you for decades, so you need a plan for how you’ll draw from them. A sustainable withdrawal strategy considers which accounts to tap into first, like your 401(k)s and IRAs, and how to manage the tax implications of each withdrawal. Understanding these rules is key to making your money last. Creating a personalized financial plan can help you structure these withdrawals to support your lifestyle while being as tax-efficient as possible, ensuring your nest egg lasts as long as you do.

Plan for Inflation and Market Swings

Your retirement could last 30 years or more, and in that time, the cost of living will rise. That’s inflation, and your budget needs to account for it. At the same time, the stock market will have its ups and downs. A good retirement plan doesn’t ignore these realities; it includes an investment strategy designed to grow your money enough to outpace inflation without taking on unnecessary risk. Proper asset management focuses on building a balanced portfolio that can weather market volatility and provide the income you need, helping you feel secure no matter the economic climate.

Set Up Your Emergency Fund

Unexpected expenses don’t stop just because you’ve retired. A new roof or a surprise medical bill can pop up at any time. That’s why having a dedicated emergency fund is so important. This isn’t your investment money; it’s a separate, easily accessible cash reserve to cover life’s curveballs. A good rule of thumb is to have at least six months of essential living expenses saved. This financial cushion gives you peace of mind and prevents you from having to sell investments at a bad time to cover an emergency. You can use online financial calculators to figure out the right amount for your fund.

Build Your Financial Team

You don’t have to figure out every detail of retirement planning on your own. In fact, you shouldn’t. Assembling a team of trusted professionals is one of the smartest moves you can make to protect your financial future. Think of it as creating a personal board of directors for your retirement, with each member bringing specialized expertise to the table. A strong team helps you see the complete picture, ensuring your investment, tax, and legal strategies all work together seamlessly.

This collaborative approach helps you make informed decisions and avoid common pitfalls as you transition from working to retirement. Your team can help you weigh complex choices, from when to take Social Security to how to withdraw from your accounts most efficiently. With the right people in your corner, you can feel confident that your plan is built on a solid foundation. At Endeavor, our process is designed to be collaborative, working with you to build a strategy that fits your life.

Find the Right Financial Advisor

Your financial advisor is the quarterback of your retirement team. They look at your entire financial situation, from your savings and investments to your long-term goals, and help you create a cohesive plan to get you where you want to go. A great advisor does more than just manage your portfolio; they act as your guide, helping you make adjustments as your life and the market change. When looking for an advisor, find someone who understands the specific challenges and opportunities that come with being a pre-retiree or a business owner. They should be someone you trust to provide clear, unbiased advice that always puts your interests first.

Work with Tax and Legal Experts

Retirement introduces a new set of tax and legal considerations. Your income sources will change, and you’ll need a strategy for tax-efficient withdrawals from your retirement accounts. A certified public accountant (CPA) or tax professional can be an invaluable part of your team, helping you minimize your tax burden and handle things like Required Minimum Distributions (RMDs). Similarly, an estate planning attorney can help you get your legal documents in order, including your will, trusts, and healthcare directives. Your financial advisor can work directly with these experts to ensure every part of your financial life is aligned, from your investments to your estate plan.

Schedule Regular Check-ins

Building your team is the first step, but maintaining the relationship is just as important. Your financial plan isn’t something you can set and forget. Life changes, your goals may shift, and financial markets are always evolving. That’s why scheduling regular check-ins with your financial advisor is so important. These meetings, whether they happen once or twice a year, are your opportunity to review your progress, discuss any changes in your life, and make sure your strategy is still on track. Consistent communication keeps everyone on the same page and ensures your plan adapts right along with you. Ready to start the conversation? You can always book a meeting with our team.

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Frequently Asked Questions

Why is calculating my net worth so important before planning for retirement? Think of it like using a map: you can't figure out the best route to your destination without knowing your exact starting point. Calculating your net worth gives you that clear, honest baseline. It moves you from guessing about your finances to knowing precisely what assets and debts you have, which is the foundation for every other decision you'll make for your retirement.

Is it always best to pay off my mortgage before I retire? Not necessarily, and this is a great question. While the emotional security of owning your home free and clear is a powerful motivator, it might not always be the most strategic financial move. If you have a mortgage with a very low interest rate, for example, your money might generate better returns in an investment account. It's a personal decision that requires weighing the peace of mind against the math of your specific situation.

What's the biggest factor in deciding when to claim Social Security? The main consideration is a trade-off between receiving smaller monthly payments for a longer time or larger monthly payments for a shorter time. Your decision should really depend on your complete financial picture. Consider your other income sources, your health, and your family's needs. There isn't a single right answer for everyone, so it's about choosing the timing that best supports your unique retirement plan.

How do I plan for healthcare costs if they're so unpredictable? You're right, you can't predict the exact number, but you can build a strong framework to handle whatever comes your way. This means doing your homework on Medicare options before you turn 65, deciding if long-term care insurance fits into your plan, and budgeting for routine out-of-pocket costs like dental and vision. A well-funded emergency fund is also a key part of this strategy, acting as a buffer for any surprise medical bills.

I have savings, but how do I turn that into a regular "paycheck" in retirement? This is the central question of a good withdrawal strategy. The process involves creating a sustainable plan for which accounts to draw from and in what order, all while considering the tax implications. The goal is to create a predictable income stream that covers your lifestyle expenses without depleting your nest egg too quickly. A financial professional can help you structure this plan to make your savings last throughout your retirement.