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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.
It’s often better to consult a professional financial advisor who can help you create a customized plan that accounts for your income, investments and expenses. A financial advisor can also help you change or modify your plan after you retire. On average, people working with financial advisors see their net returns rise by 3%, according to a Vanguard report.
With Vanguard, you can connect with a personal advisor who can help assess how you’re doing so far and make sure you’ve got the right portfolio to meet your goals on time.
Their hybrid advisory system combines advice from professional advisers and automated portfolio management to make sure your investments are working to achieve your financial goals. All you have to do is fill out a brief questionnaire about your financial goals, and Vanguard’s advisers will help you set a tailored plan, and stick to it.
Once you’re set, Vanguard’s advisors manage your portfolio. Because they’re fiduciaries, they don’t earn commissions, so you can trust that the advice you’re getting is unbiased.
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.
Read more: Want an extra $1,300,000 when you retire? Dave Ramsey says this 7-step plan ‘works every single time’ to kill debt, get rich in America — and that ‘anyone’ can do it
This isn’t surprising, given that credit card debt reached a record high of $1.21 trillion in the fourth quarter of 2024, according to the Federal Reserve Bank of New York. What’s more, 11.12% of people were just making minimum payments on their credit cards — a 12-year high — according to data from the Federal Reserve of Philadelphia.
As such, planning to eliminate or minimize your non-mortgage debt could help boost your retirement. But if you’re struggling with multiple credit cards and high-interest debt, one way to start regaining control is by tapping into your home’s equity through a Home Equity Line of Credit (HELOC).
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
One reason many seniors have debt is because of unexpected medical expenses. Roughly 17% of seniors carry an average of $9,144 in debt due to outstanding medical bills, according to the same National Debt Relief survey.
Don’t underestimate just how expensive medical bills can be in your senior years. Try to set up a plan in anticipation of unexpected medical 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.
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.
You could always wait until you stop working to plan your estate. However, managing your estate and retirement plans simultaneously can help you maximize potential tax advantages and other benefits. Plus, premiums tend to increase as you age, so locking in a low rate now can help you protect your loved ones tomorrow without breaking the bank today.
For that reason, consider planning your estate before your working days come to an end.
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, home and auto insurance expenses often account for a significant proportion of your monthly expenses. Americans spend an average of 3.39% of their total household income on car insurance in 2025, marking a 12% increase from last year.
Home insurance rates are also shooting up. On average, homeowners insurance premiums have increased by 24% over the last three years, according to Consumer Federation of America.
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.
What’s more, you can save about $482 a year — that’s extra money to fund your retirement lifestyle — by shopping around and comparing home insurance rates through OfficialHomeInsurance.com.
Get started and find the best deals for you from nearby insurers in just two 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.
