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Most people spend countless hours planning their retirement before the big day finally arrives. After all, it usually takes a lifetime 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 an annual 2025 retirement study by Allianz Life, 64% of Americans are more worried about running out of money in retirement than they are about dying (1).
But intentional and focused planning can help you shake those fears.
As personal finance commentator Dave Ramsey says, “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 overall goal (2).”
With that in mind, here are six milestones you should try to reach to feel more confident about your retirement plan.
One of the biggest concerns for retirees is having enough money to survive without a salary.
Financial advisors often cite the “rule of 25,” which says 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 your annual expenses or the amount of income your assets will realistically generate each year in retirement.
Working with a financial advisor can be extremely beneficial—they can help you create a customized plan based on your finances and adjust it as your needs change, even 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 ultra-rich 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 any level.
Advisor.com can quickly match you with an advisor who can guide you through your options. The platform’s advisors are fiduciaries, which means they are legally bound to act in your best interest.
Just answer a few questions about your investment timeline and goals, and Advisor.com will match you with a vetted and experienced fiduciary financial advisor.
Book a free, no-obligation call today to see if they’re right for your needs.
Carrying debt without work income doesn’t make for a fun retirement, and unfortunately, many retirees live with this burden.
“Debt isn’t just borrowing money you don’t have from the bank. It’s also borrowing from your future,” Ramsey wrote on his blog (4). “Every dollar that goes toward paying down debt is a dollar that you could have invested. If you’re serious about saving for the future, the debt has to go away.”
According to a survey by National Debt Relief, 72% of Americans over 55 have accumulated some debt, with more than half admitting to having it “held back” in their lives (5).
This is no surprise, given that total household debt reached a staggering $18.59 trillion in the third quarter of 2025, with credit card debt accounting for $1.23 trillion, according to the Federal Reserve Bank (6). Worse, 10.71% of people only made minimum payments on their credit cards (7).
It’s important to prioritize paying off high-interest debt. Consider using strategies like the avalanche method, which focuses on paying off the highest-interest debt first. Or opt for the snowball method, which aims to pay off the smallest debts first to build momentum.
Read more: Approaching retirement with no savings? Don’t panic, you are not alone. Here are 6 easy ways to catch up (and fast)
Nearly 97.1% of Americans of retirement age have non-mortgage debt, with the average balance reaching $11,349, according to LendingTree (8).
One of the main causes of this debt is unexpected medical expenses. Medical bills can be surprisingly expensive in your later years, so it’s wise to plan ahead for potential health care costs before you retire.
Americans under the age of 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 postcode, age and household income, and the U65 will display quotes from suppliers near you within five minutes. You can compare policies and coverage from Aetna, Kaiser, Anthem, Oscar Health and other providers for free, helping you make an informed decision.
If you have enough assets to retire, you may have something to leave behind for your family after you’re gone. By 2045, the largest generational transfer of wealth in history is expected to occur, with an estimated exchange of $68 to $84 trillion, according to the Michigan Journal of Economics (9). If you have enough assets to retire, you may have something to roll over too.
While you might wait until retirement to plan your wealth, starting earlier allows you to maximize tax benefits and lock in lower insurance premiums.
Acting now can help protect your loved ones and avoid unnecessary costs down the road.
Opting for term life insurance through a provider like Ethos ensures that as you age, your loved ones are protected from unexpected costs. With term life insurance, you can ensure affordable coverage while managing your other financial responsibilities.
You can get a policy with up to $2 million in coverage in just five minutes, starting at just $2/day.
To get a free quote, simply answer a few questions about yourself. From there, you can compare various policies and choose one that best suits your needs.
The 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 their work. Most people spend so much time working and raising children that they cannot maintain relationships outside of these two worlds.
This is a recipe for loneliness and boredom in retirement. In fact, 36% of seniors said they considered going back to work because they were bored, according to a survey of resume templates (10).
That’s why it’s important to create a social and mental health plan before you retire. Don’t leave your job unless you have a good idea of what you’re going to do with your time.
Consider a trial before you retire. This might include taking a month or two off 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’re overspending.
For example, car insurance costs are often a significant proportion of your monthly expenses. Americans spent an average of 3.39% of their total household income on auto insurance in 2025, a 12% increase from last year (11).
Shopping 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 car 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 as low as $29/month in minutes.
As you get closer to retirement, every dollar starts to count more. Rising health care costs, uncertain markets and fixed incomes can make stretching your savings more difficult, especially if you’re trying to plan decades into the future.
That’s where senior-focused organizations like AARP come in. Members can unlock discounts on almost everything – from prescriptions and dental plans to travel, entertainment and insurance.
AARP members also have 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, which can save you thousands.
Join AARP today and get 25% off your first year.
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Allianz Life (1); Ramsey Solutions (2), (4); Bank of America (3); Reduction of national debt (5); Federal Reserve Bank of New York (6); FRED (7); LendingTree (8), (12); Michigan Journal of Economics (9); Resume Templates (10); Bank rate (11)
This article provides information only and should not be construed as advice. Offered without warranty of any kind.
