8 questions to ask yourself when planning for retirement
From long-term retirement income to healthcare, here are important questions to ask yourself when preparing for retirement.
Preparing for retirement can be an exciting time, but it can also spur a lot of questions about the unknown. No matter what you envision for retirement, it’s important to have a plan. Here are some answers to common questions you might have as you start to reach retirement age.
1. What will I do after retirement?
When deciding how to spend your days after retirement, it’s time to start thinking about your priorities.
Do you want to spend more time traveling? Pursue new or existing hobbies? Spend more time with friends or family? Once you have a better vision for your retirement goals, you can more effectively create a roadmap for how you want to get there. Here are a few ideas to get you started on your retirement bucket list.
2. When should I retire?
There is no “correct” age to retire. Taking early retirement — before your full retirement age — may be a good option for you. This allows you more time to do what you want, but it may have long-term financial implications for your retirement savings. It’s also important to remember that you can’t claim Medicare until you reach age 65, so you’ll need to purchase health insurance coverage in the interim.
You may prefer to continue working, due to personal or financial needs. Retiring later can have financial benefits as you’ll receive a higher Social Security benefit and will have more time to build your retirement savings.
3. When should I claim Social Security?
Social Security retirement benefits will likely play a role in the majority of people’s retirement decisions. When planning to collect Social Security, there are important ages that will factor into how you design your retirement income plan.
The earliest age you can claim Social Security benefits; however, claiming at an early age reduces the amount of your benefits.
66-67 is full retirement age, depending on the year you were born; when you reach it you can claim Social Security with no reduction in benefits due to your age.
The age Social Security benefits stop accumulating; there’s no gain from delaying claiming benefits after you turn 70.
While you can apply for Social Security benefits any time between age 62 and 70, the amount will be higher the longer you wait, up to age 70. You can learn more about Social Security retirement benefits on the Social Security website.
4. How can I apply for Social Security benefits?
You can apply for Social Security benefits online at the Social Security website, and submit your application up to four months before you want your income payments to start. You will receive a letter within 30 days letting you know if your application was approved. You can also apply in person. Visit ssa.gov/locator to find the nearest location and schedule an appointment.
5. How will I pay for health care in retirement?
The vast majority of people become eligible for Medicare at age 65. You can sign up for Medicare Part A and B from the Social Security website.
When you enroll you’ll be able to select the coverages you want, some of which include paying a premium. You will also be able to choose between traditional Medicare, or a private Medicare Advantage plan.
Medicare can be confusing and it’s a good idea to consult a financial professional as choices can have long-term impacts. You can learn more in this Medicare guide.
6. How will I create income in retirement?
A good plan is to have a well-rounded portfolio with income coming from multiple sources.
Investment savings accounts like 401(k)s and individual retirement accounts (IRAs) provide a steady source of income through withdrawals over time. They also continue to provide potential market-based growth for your savings. But because these income sources are linked to market performance, it’s possible their account value could decrease in bear markets, even before you take withdrawals.
That’s why it’s important to also include sources that provide guaranteed income, like Social Security, workplace pensions, and other long-term retirement income products like fixed index annuities. You can count on guaranteed income to pay your bills each month, no matter what’s happening in the market.
7. Should I have an estate plan?
You never know what the future might hold, but having an estate plan can help provide assurance that you and your family will be protected financially. Retirement is a great time to work with a financial advisor and attorney; they can help you take care of the paperwork and legal documents needed to protect your assets and make sure they go where and to whom you want when you’re no longer here. Adding products like annuities to your portfolio can help make this process easier by allowing you to name beneficiaries.
8. Should I work with a financial professional?
Yes. Preparing for retirement can involve numerous tasks that need to be managed. Financial professionals can offer advice and guidance about investments, personal finances, and retirement planning.
Published June 29, 2026