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Many people spend countless hours planning their retirement before the big day finally arrives. After all, it usually takes a lifetime of savings to confidently exit the workforce and enter your golden years.
But the rising cost of living and the ongoing affordability crisis are making retirement planning more difficult. According to the 2025 Annual Retirement Study conducted by Allianz Life, 64% of Americans worry more about running out of money in retirement than about death (1).
But deliberate and focused planning can help you overcome these fears.
As personal finance commentator Dave Ramsey puts it, “A retirement plan takes a big, sometimes hard-to-imagine goal, and breaks it down into small, manageable steps you can take now (and keep taking) until you reach that big-picture goal (2).”
With that in mind, here are six milestones you should hit to feel more confident in your retirement planning.
One of the biggest concerns for retirees is having enough money to survive 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 does not account for 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 finances and adjust as your needs change in retirement.
More than 90% of wealthy Americans work with financial advisors and report high satisfaction with the guidance they receive, according to a Bank of America survey (3). However, you don’t have to be super rich to take advantage of professional guidance.
A trusted, pre-screened financial advisor can help you develop a solid retirement strategy and protect your assets at any level.
Advisor.com can quickly match you with an advisor who can guide you through your options. The platform’s advisors are fiduciaries, meaning they are legally bound to act in your best interest.
Answer a few questions about your investment timeline and your goals, and Advisor.com will match you with a vetted, experienced financial advisor.
Book a free, no-obligation call today to see if they’re a good fit for your needs.
Carrying debt without employment income does not make for an enjoyable retirement, and unfortunately, many retirees live with this burden.
“Debt isn’t just money you don’t have from the bank, it’s borrowing from your future,” Ramsey wrote on his blog (4). “Every dollar that goes into debt payments is a dollar you could be investing. If you’re serious about saving for the future, the debt has to go.”
According to a National Debt Relief survey, 72% of Americans over 55 have accumulated some debt, with more than half admitting that it has “held them back” in life (5).
According to the Federal Reserve Bank (6), total household debt hit an astonishing $18.59 trillion in the third quarter of 2025, with credit card debt at $1.23 trillion, which is no surprise. Even worse, 10.71% of people were making only the minimum payment on their credit cards (7).
It is important to prioritize paying off high interest debt first. Consider using strategies like the avalanche method, which focuses on paying off your highest-interest debt first. Or opt for the snowball method, which aims to pay off the smallest debt first to build momentum.
Read more: Approaching retirement with no savings? Fear not, you are not alone. Here are 6 easy ways you can catch up (and fast).
About 97.1% of Americans of retirement age carry non-mortgage debt, with the median balance reaching $11,349, according to LendingTree (8).
One of the major causes of this debt is unexpected medical expenses. Medical bills can be surprisingly expensive in your senior years, so it’s wise to plan for potential health care costs before you retire.
Americans under 65 — even those with pre-existing health conditions — can compare rates and features of health insurance policies from reputable providers through U65 Health Insurance.
The process is simple: enter your zip code, age and household income, then the U65 will display quotes from providers near you within five minutes. You can compare free policies and coverage by providers like Aetna, Kaiser, Anthem, Oscar Health and more, helping you make an informed decision.
If you have enough assets to retire, you may have something to leave behind for your family when you’re gone. According to the Michigan Journal of Economics (9), by 2045, the largest generational wealth transfer in history is expected, with an estimated $68 to $84 trillion changing hands. If you have enough assets to retire, you might as well 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 down the road.
Opting for term life insurance through a provider like Ethos ensures that your loved ones are protected from unexpected costs as you age. With term life insurance, you can secure affordable coverage while managing your other financial responsibilities.
You can get a policy with coverage up to $2 million in just five minutes, starting at just $2/day.
To get a free quote, just answer a few questions about yourself. From there, you can compare different policies and choose the one that suits your needs.
Ethos’ application process ensures you get flexible coverage options quickly and transparently, allowing you to focus on what matters most.
After decades of building a career or business, a retiree’s identity is often tied to his work. Most people spend so much time working and raising children that they can’t nurture these two out-of-this-world relationships.
This is a recipe for loneliness and boredom in retirement. In fact, 36% of seniors said they’ve considered returning to work because they’re bored, according to a Resume Templates survey (10).
That’s why it’s important to have a social and mental health plan before you retire. Don’t quit your job until you have a good idea of what you’ll do with your time.
Consider a test run before you retire. This may include taking a month or two off work to experience retirement before you officially retire.
Use this time to meet people or complete the activities you included in your social plan to determine if adjustments are needed.
Taking a closer look at your budget can also help you identify areas where you spend more.
For example, auto insurance costs often account for a significant proportion of your monthly expenses. Americans spent an average of 3.39% of their gross household income on car insurance in 2025, a 12% increase from last year (11).
Shopping around and comparing rates from different providers can help lower your premiums. According to a LendingTree survey, 92% of Americans who shopped for auto insurance rates saved money by switching carriers (12).
OfficialCarInsurance.com can help you compare auto insurance policies from reputable insurers near you for free.
Once you answer a few basic questions like your age, driving history and the vehicle you want to insure, OfficialCarInsurance.com will show you quotes starting at just $29/month in minutes.
As you get closer to retirement, every dollar starts to matter more. Rising health care costs, uncertain markets and fixed incomes can make it difficult to stretch your savings—especially if you’re trying to plan for decades ahead.
That’s where senior-focused organizations like AARP come in. Members can unlock discounts on almost everything — from prescription and dental plans to travel, entertainment and insurance.
AARP members also get access to guides that can 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.
Sign up with AARP today and get 25% off your first year.
We rely only on vetted sources and reliable third-party reporting. For details, see our editorial ethics and guidelines](https://moneywise.com/editorial-ethics-and-guidelines)).
Allianz Life (1); Ramsay solution (2), (4); Bank of America (3); National Debt Relief (5); Federal Reserve Bank of New York (6); Fred (7); LendingTree (8), (12); Michigan Journal of Economics (9); Resume Templates (10); bankrate (11)
This article provides information only and should not be construed as advice. It is provided without warranty of any kind.
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