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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 of saving to confidently exit the workforce and enter your golden years.
But the rising cost of living and ongoing affordability crunch are making retirement planning more difficult. According to a 2025 Annual retirement study conducted by Allianz Life, 64% of Americans are more worried about running out of money during retirement than the are about death (1).
But intentional and focused planning can help you shake off 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 aim to hit to feel more confident in your retirement plan.
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 says that you can retire comfortably if your assets are worth at least 25 times your annual expenses. However, this rule of thumb doesn’t account for changes in yearly spending or the amount of income your assets will realistically generate each year in retirement.
Working with a financial advisor can be highly beneficial — they can help you create a personalized 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-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 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 obligated to act in your best interest.
Just answer a few questions about your investment timeline and your goals, and Advisor.com will match you with a vetted, experienced fiduciary financial advisor.
Book a free, no-obligation call today to see if they’re the right fit for your needs.
Carrying debt without employment 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 to a debt payment is a dollar you could have invested. If you want to be serious about saving for the future, debt has got to go.”
According to a survey from National Debt Relief, 72% of Americans over 55 have accumulated some debt, with more than half admitting it has “held them back” in life (5).
This comes as no surprise, considering total household debt hit an astonishing $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 still, 10.71% of people were making only minimum payments on their credit cards (7).
It’s 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 at paying off the smallest debts first to build momentum.
Read More: Approaching retirement with no savings? Don’t panic, you’re not alone. Here are 6 easy ways you can catch up (and fast)
Nearly 97.1% of Americans at retirement age carry non-mortgage debt, with the median balance reaching $11,349, according to LendingTree (8).
One of the leading causes of this debt is unexpected medical expenses. Medical bills can be surprisingly costly in your senior 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 zip code, age and household income, then U65 will display quotes from providers near you within five minutes. You can compare policies and coverage by Aetna, Kaiser, Anthem, Oscar Health and more 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 wealth transfer in history is projected to take place, with an estimated $68 to $84 trillion changing hands, according to the Michigan Journal of Economics (9). If you have enough assets to retire, you too may have something to pass on.
While you could wait until retirement to plan your estate, starting sooner allows you to maximize tax benefits and lock in lower insurance premiums.
Taking action 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 secure 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.
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 can’t nurture relationships outside of these two worlds.
This is a recipe for loneliness and boredom in retirement. In fact, 36% of seniors said they have considered going back to work because they’re bored, according to a Resume Templates survey (10).
This is 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 about what you will do with your time.
Consider a trial run before you retire. This could 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’ve included in your social plan to determine whether adjustments are needed.
Taking a closer look at your budget can also help you identify areas where you overspend.
For instance, auto insurance expenses often account for a significant proportion of your monthly expenses. Americans spent an average of 3.39% of their total household income on car insurance in 2025, marking a 12% increase from last year (11).
Shopping around and comparing rates from different providers can help reduce your premiums. According to a LendingTree survey, 92% of Americans who shopped around 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 some basic questions like your age, driving history and the vehicle you want to insure, OfficialCarInsurance.com will display quotes starting at just $29/month within 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 harder 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 prescriptions and dental plans to travel, entertainment and insurance.
AARP members also get access to guides that can help you make the most 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.
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Allianz Life (1); Ramsey Solutions (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.