May 11, 2025
Most people spend countless hours planning their retirement before the big day finally arrives. After all, it’s not always easy to feel completely confident before you exit the workforce and enter your golden years.
With that in mind, here are six milestones you should aim to hit in order to feel more confident in your retirement plan.
1. Comprehensive income and expense plan
One of the biggest concerns for retirees is whether they have enough money to survive without a paycheck.
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Financial advisors often cite the 'rule of 25', which states that you can expect to retire comfortably if your assets are worth at least 25 times your annual expenses. However, this rule of thumb doesn’t guarantee how much you can spend each year, or how much income your assets will realistically generate every year in retirement.
It’s likely 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.
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2. Debt elimination
Carrying debt without employment income doesn’t often make for a fun retirement and, unfortunately, many retirees live with this unpleasant 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.
With this in mind, you should plan to eliminate or minimize your non-mortgage debt before you retire.
3. Healthcare plan
One of the reasons many seniors have debt is because of unexpected medical expenses. The same National Debt Relief survey found that roughly 17% of seniors carry an average of $9,144 in debt due to outstanding medical bills.
Don’t underestimate just how expensive medical bills can be in your senior years. With this in mind, you’d be wise to set up a robust plan to deal with these medical costs before you retire.
Read More: Dave Ramsey says this 7-step plan ‘works every single time’ to kill debt, get rich in America — and that ‘anyone’ can do it
4. Estate plan
If you have enough assets to retire, you may have something to leave behind for your heirs 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.
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For that reason, consider planning your estate before your working days come to an end.
5. 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 have little time to 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 or who you will spend your time with.
6. 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 that you can assess whether you need to make any adjustments.
If your mini-retirement isn’t as fun or fulfilling as expected, you can consider delaying retirement for a few years.
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Vishesh Raisinghani is a financial journalist covering personal finance, investing and the global economy. He's also the founder of Sharpe Ascension Inc., a content marketing agency focused on investment firms. His work has appeared in Moneywise, Yahoo Finance!, Motley Fool, Seeking Alpha, Mergers & Acquisitions Magazine and Piggybank.
