Moneywise and Yahoo Finance LLC may earn commission or revenue from the links below.
Most people spend countless hours planning their retirement before the big day finally arrives. After all, it often takes a lifetime of savings to confidently exit the workforce and enter your golden years.
But rising costs of living and an ongoing affordability crunch are making retirement planning more difficult. According to the 2025 Annual Retirement Study conducted by Allianz Life, 64% of Americans are more worried about running out of money during retirement than they are about dying(1).
But intentional and targeted planning can help you escape these fears.
As personal finance commentator Dave Ramsey says, “Retirement planning takes a big, sometimes unimaginable goal and breaks it down into small, manageable steps you can take now (and keep taking) until you achieve your overall goal(2).”
With that in mind, here are six milestones you should strive to achieve to feel more confident in your retirement plan.
One of the biggest concerns for retirees is having enough money to live on without a paycheck.
Financial advisors often cite the “Rule of 25,” which states that you can retire comfortably if your assets are worth at least 25 times your annual expenses. However, this rule of thumb doesn’t take into account changes in annual expenses or the amount of income your assets will actually generate each year in retirement.
Working with a financial advisor can be very beneficial—they can help you create a personalized plan based on your financial situation and adjust it as your needs change, even in retirement.
A Bank of America survey revealed that more than 90% of wealthy Americans work with financial advisors and are highly satisfied with the guidance they receive (3). However, you don’t have to be wealthy to take advantage of professional guidance.
A trusted, pre-screened financial advisor can help you develop a solid retirement strategy and protect your wealth at every level.
Advisor.com can quickly match you with an advisor to guide you through your choices. The platform’s advisors are fiduciaries, which means they have a legal obligation to act in your best interests.
Just answer a few questions about your investing timeline and goals, and Advisor.com will match you with a vetted, experienced fiduciary financial advisor.
Schedule a free call today to see if they’re right for your needs.
Carrying debt with no employment income does not make for an enjoyable retirement, and unfortunately, many retirees are burdened with this burden.
“Debt isn’t just borrowing money from a bank. It’s also borrowing money from your future,” Ramsey writes on his blog (4). “Every dollar you use to pay down debt can be invested. If you want to be serious about saving for the future, you have to get out of debt.”
According to a survey by the National Debt Relief Organization, 72% of Americans over the age of 55 have accumulated some debt, with more than half admitting that debt is “holding back their lives” (5).
This is not surprising considering total household debt reached a staggering $18.59 trillion in the third quarter of 2025, according to the Federal Reserve, with credit card debt reaching $1.23 trillion (6). Even worse, 10.71% only use their credit card to pay the minimum payment(7).
It’s important to prioritize paying off high-interest debt first. Consider using a strategy like the avalanche method, which focuses on paying off the debt with the highest interest first. Or choose the snowball method, which aims to pay off the smallest debt first to build momentum.
Read more: Nearing retirement but no savings? Don’t panic, you’re not alone. Here are 6 easy ways you can catch up (and fast)
According to LendingTree, nearly 97.1% of retirement-age Americans carry non-mortgage debt, with the median balance reaching $11,349(8).
One of the main causes of this debt is unexpected medical bills. Medical expenses in old age can be very expensive, so it’s wise to plan ahead for potential health care expenses before retirement.
Americans under the age of 65, and even those with pre-existing health conditions, can compare rates and features of health insurance policies from reputable providers with U65 Health Insurance.
The process is simple: enter your postcode, age and household income, and within five minutes U65 will display quotes from providers near you. You can compare policies and coverage from Aetna, Kaiser, Anthem, Oscar Health and more providers for free to help you make an informed decision.
If you have enough assets to retire, you may be able to leave something to your family when you pass away. According to the Michigan Journal of Economics, by 2045, the largest intergenerational wealth transfer in history is expected to occur, with the amount expected to change hands reaching $68 to $84 trillion(9). If you have enough assets to retire, you may also have something to pass on.
While you can wait until retirement to plan your estate, starting early allows you to maximize tax benefits and lock in lower insurance premiums.
Taking action now can help protect your loved ones and avoid unnecessary expenses in the future.
Choosing term life insurance through a provider like Ethos can ensure your loved ones are protected from unexpected expenses as you age. With term life insurance, you can get affordable coverage while managing your other financial responsibilities.
It only takes 5 minutes to get a policy with coverage up to $2 million, starting at just $2 a day.
To get a free quote, just answer a few questions about yourself. From there, you can compare various policies and choose the one that best suits your needs.
Ethos’ application process ensures you have fast, transparent access to flexible coverage options, allowing you to focus on what matters most.
After decades of career or business development, a retiree’s identity is often tied to their job. Most people spend too much time working and raising children to cultivate relationships outside of these two worlds.
This is a source of loneliness and boredom in retirement. In fact, 36% of seniors said they had considered going back to work because they were bored, according to a resume template survey(10).
That’s why it’s important to have a social and mental health plan in place before retirement. Don’t leave work unless you know exactly what you want to spend your time doing.
Consider doing a trial run before retiring. This may include taking a month or two off to experience retirement life before officially retiring.
Use this time to meet people or complete activities you’ve included in your social plans to determine if adjustments need to be made.
Taking a closer look at your budget can also help you identify areas where you are overspending.
For example, car insurance costs often make up a large portion of your monthly expenses. In 2025, Americans will spend an average of 3.39% of their total household income on auto insurance, an increase of 12% from last year (11).
Shopping around and comparing rates from different providers can help you lower your premiums. A LendingTree survey shows that 92% of Americans save money by switching carriers when shopping for auto insurance rates (12).
OfficialCarInsurance.com can help you compare car insurance policies from reputable insurance companies near you for free.
Once you answer some basic questions, such as your age, driving history and the vehicle you want to insure, OfficialCarInsurance.com will display quotes within minutes, starting at just $29/month.
As retirement age approaches, every dollar starts to matter more. Rising health care costs, uncertain markets and a fixed income can make it harder to grow your savings — especially if you want to plan for decades into the future.
That’s where senior-focused organizations like AARP come in. Members receive discounts on nearly everything—from prescription drugs and dental plans to travel, entertainment, and insurance.
AARP members also receive guidance to help you get the most out of Social Security, choose the right Medicare plan and find other government benefits you may qualify for – potentially saving you thousands of dollars.
Join AARP today and get 25% off your first year.
We rely only on vetted sources and reliable third-party reports. For more information, please see our Editorial Ethics and Guidelines](https://moneywise.com/editorial-ethics-and-guidelines)).
Allianz Life (1); Ramsey Solutions (2), (4); Bank of America (3); National Debt Relief (5); Federal Reserve Bank of New York (6); Fred (7); Lending Tree (8), (12); Michigan Journal of Economics (9); Resume Templates (10); Bank Rates (11)
This article provides information only and should not be considered advice. It is provided without any warranty of any kind.
