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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.
With that in mind, here are six milestones you should aim to hit to feel more confident in your retirement plan.
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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. 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.
FinancialAdvisor.net is a free online service that helps you find a financial advisor who can help you create a plan to reach your financial goals. Just answer a few questions and their extensive online database will match you with a few vetted advisors based on your answers.
You can view advisor profiles, read past client reviews, and schedule an initial consultation for free with no obligation to hire.
2. Eliminate your debt
Carrying debt without employment income doesn’t make for a fun retirement, and unfortunately, many retirees live with this burden.
According to a survey from National Debt Relief, 72% of Americans over 55 have accumulated some debt, with more than half admitting it’s “held them back” in life.
This comes as no surprise, considering total household debt hit an astonishing $18.20 trillion in the first quarter of 2025, with credit card debt accounting for $1.18 trillion, according to the Federal Reserve Bank. Worse still, 11.12% of people were making only minimum payments on their credit cards—a 12-year high.
Reducing or eliminating your non-mortgage debt can significantly improve your retirement outlook. If you’re dealing with multiple credit cards and high-interest debt, tapping into your home’s equity through a Home Equity Line of Credit (HELOC) can help you regain control. Americans currently hold over $ 34.7 trillion in home equity—surpassing the entire U.S. GDP, according to Newsweek.
A HELOC is a secured line of credit that leverages your home as collateral. Depending on the value of your home and the remaining balance on your mortgage, you may be able to borrow funds at a lower interest rate from a lender as a form of revolving credit.
Rather than juggling multiple bills with varying due dates and interest rates, you can consolidate them into one easy-to-manage payment. The results? Less stress, generally reduced fees, and the potential for significant savings over time.
LendingTree’s marketplace connects you with top lenders offering competitive HELOC rates. Instead of going through the hassle of shopping for loans at individual banks or credit unions, LendingTree lets you compare multiple offers in one place. This helps you find the best HELOC for your situation.
Terms and conditions apply. NMLS#1136.
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.
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 healthcare 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.
Read more: Warren Buffett used 8 simple money rules to turn $9,800 into a stunning $150B — start using them today to get rich (and then stay rich)
4. Create an estate plan
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. 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.
You can get a term life insurance policy without taking extensive medical tests with Ethos.
You can get coverage of up to $3 million in three simple steps. The best part? The process takes about 10 minutes, with premiums starting at $2/day.
5. Prepare a mental and Social Plan
After decades of building a career or business, a retiree’s identity is often wrapped up in their work. Most people spend so much time working and raising children that they can’t nurture relationships outside of these two settings.
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.
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 from work to experience retirement before you officially call it a career.
Use this time to meet the people or do the activities that you’ve included in your social plan so you can see if 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.
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.
OfficialCarInsurance.com lets 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.
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This article provides information only and should not be construed as advice. It is provided without warranty of any kind.