Retiring soon? Here are 6 must-hit milestones to check off before diving into retirement

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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 swim into your golden years.

But the rising cost of living and ongoing affordability crunch can make 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 they are about death (1).

But intentional and focused planning can help you shake off these fears and reach clear water.

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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.

1. Develop a comprehensive income and expense 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).

For those struggling with the cost-of-living crisis, the One Big Beautiful Bill act offered some immediate, albeit temporary, relief. Those aged 65 and above can now claim a bonus tax deduction of $6,000 for single filers or $12,000 for joint filers. But taking advantage of these changes might be difficult on your own, especially since these measures are set to expire after the 2028 tax year. Taking full advantage requires a precise approach to ensure you aren’t leaving money on the table — or triggering an accidental audit.

This is especially critical for retirees with a portfolio of $250,000 or more. When larger portfolios are involved, tax decisions become less about filing and more about strategy.

In these cases, working with a financial advisor can help reduce costly oversights. Platforms like WiserAdvisor can connect you with vetted professionals who specialize in this kind of planning.

How it works:

Share your goals: You provide a few details about your savings, retirement timeline and your investment portfolio

Note: WiserAdvisor is a matching service and does not provide financial advice directly. All matched advisors are third parties, and specific financial results are not guaranteed.

2. Eliminate your debt

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.

Another option is consolidating your existing debt through one personal loan, ideally at a lower interest rate.

If you have considerable equity in your home, you may consider consolidating your high-interest debt into a low-interest HELOC or home equity loan.

Having access to your home equity could help to cover unexpected expenses, pay substantial debt, fund a major purchase like a home renovation or supplement income from your retirement nest egg.

Rates on HELOCs are typically lower than APRs on credit cards and personal loans, making it an appealing option for homeowners with substantial equity.

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3. Find a good healthcare plan

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.

If you want to absorb some of the costs of a sudden medical expense, an emergency fund could help take some of the bite out — especially if coupled with good quality insurance.

A high-yield account like a Wealthfront Cash Account can be a great place to grow your uninvested cash, offering both competitive interest rates and easy access to your money when you need it.

A Wealthfront Cash Account currently offers a base APY of 3.30% through program banks, and new clients can get an extra 0.75% boost during their first three months on up to $150,000 for a total variable APY of 4.05%.

That’s ten times the national deposit savings rate, according to the FDIC’s April report.

Additionally, Wealthfront is offering new clients who enable direct deposit ($1,000/mo minimum) to their Cash Account and open and fund a new investment account an additional 0.25% APY increase with no expiration date or balance limit, meaning your APY could be as high as 4.30%.

With no minimum balances or account fees, as well as 24/7 withdrawals and free domestic wire transfers, your funds remain accessible at all times. Plus, you get access to up to $8M FDIC Insurance eligibility through program banks.

4. Ensure your loved ones are taken care of

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.

But getting your estate in order can take time. To protect yourself, and your family, in the meantime you way want to consider signing up for term life insurance from Ethos.

Ethos is rated “Excellent” on Trustpilot, and has an A+ rating from the Better Business Bureau (BBB). The platform offers simple and affordable coverage for a set period of time — typically between 10 and 30 years.

As a licensed third-party insurance administrator, Ethos has joined forces with some of the industry’s top insurance carriers, such as Banner Life, TruStage Financial and Ameritas Life Insurance.

Ethos gives you the flexibility to select coverage amounts ranging from $2,000 to $100,000. Premiums start at just $9.80 a month and are guaranteed throughout the term.

You can get coverage in just 10 minutes online or by phone, with no medical exams or blood tests required.

5. Prepare a mental and social plan

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.

6. Do a lifestyle trial run

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 the previous 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).

By using a comparison platform like Insurify, you can instantly view quotes from top-rated providers to ensure you aren’t paying a hidden ‘loyalty tax’ to your current insurer.

Just answer a few basic questions, and Insurify will show you the most affordable deals in as little as 3 minutes.

Not only is the process 100% free, but you could also save up to 15% by bundling your car and home insurance.

And 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.

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