Nov 11, 2026

You Can Retire Now If You Answer 'Yes' to These 6 Questions, According to Kevin Lum

You may think you’re ready to retire, but how do you know you’re ready for retirement? Unless you know, many individuals will opt to keep working year after year.

Fortunately, retirement planner and certified financial planner (CFP) Kevin Lum has walked hundreds of clients through this issue. In a YouTube video, Lum addressed the six questions you need to ask yourself to make the call. Those able to answer “yes” to these six questions can retire now.

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Sounds easy enough, right? Let’s get into it.

1. Is Your Health Suffering Because of Work?

Lum cited a February 2026 article in Psychology Today which linked retirement stress to physical symptoms. Think shoulders tightening, headaches and muscle tension. The same article said mental health counselors see an uptick in patients who are soon-to-be retirees still in the workforce who haven’t decided to leave their jobs yet.

Your health should be a key consideration when deciding when to retire, especially for workers ages 62 or older. You may decide to work one more year to keep adding to your retirement nest egg but continue spending increasingly large amounts of money on physical therapy and medications to manage workplace stress. For a lot of people, Lum said this math doesn’t make sense.

2. Have You Been Postponing Your Life?

Many retirees have bucket lists loaded with experiences and hobbies they want to live out and pick up after retirement. Why not do them now? Usually, most people will reply that they simply don’t have the time. Instead of continuing to defer your life, it may be time to consider retiring.

“There are only so many good summers left where you can physically do the things you want to do,” Lum said. For a 65-year-old, this could shake out as 15 to 20 (if lucky, more) active years ahead of you to engage in activities that require real energy.

3. Do You Know Who You Are Outside of Work?

Lum said he’s watched many successful, competent people lose themselves when they retire and it has nothing to do with a lack of preparedness. Rather, these individuals have spent the last 30 to 40 years building their entire sense of self around their job titles.

According to a 2021 study from the The Gerontologist, as reported on by SupportiveCare.com, 41% of retirees experience moderate to severe identity disruption during the first year of retirement. A separate study conducted by Harvard University revealed that those with social support outside of work experienced less mental "deterioration" as they aged.

If you can answer yes to this question, Lum said you’ve already done the hard work and figured out who you are beyond a paycheck. But if you don’t know, it’s time to start thinking about who you are and what you care about when you don’t have a full-time job.

4. Can You Financially Afford To Stop Working?

Technically, this should be the number one question to ask yourself if you think you’re ready to retire. Surprisingly, though, money is often not the thing Lum finds holds retirees back.

According to a 2026 report from the National Institute of Retirement Security, the median amount saved for retirement for workers ages 55 to 64 is $30,000. Broaden this amount out to all working Americans, including those without any retirement savings and it drops to $955. People are still retiring even if they don’t have a lot of money saved up.

If you’re unsure whether you can afford to stop working, Lum recommended asking yourself these three questions.

What are your essential expenses? Think housing, healthcare, utilities and groceries. Lum said for most people this is somewhere between $5,000 to $10,000 a month.
What guaranteed income do you already have? Some examples include Social Security, pensions and annuities. If your essential expenses are $8,000 a month, Lum said Social Security may cover $4,000 and you’ll need your portfolio to generate another $4,000 for the remaining balance.
Can your portfolio sustainably generate that additional money every month? Here you can implement a variety of withdrawal strategies or a dynamic income strategy, the latter of which Lum said can help people spend more if they have some sort of variability in their budgets.

5. Do You Know What You’ll Do All Day?

It’s a very different thing to confuse wanting to retire versus wanting to stop working for a little bit. You need to plan how to spend your newly acquired free time beyond traveling and playing golf.

“Retirement isn’t a vacation,” Lum said, adding that retirees end up with 2,500 hours of leisure time annually compared to their working life. “Structure and purpose aren’t optional. They’re what separate a great retirement from a miserable one.”

6. Are You Working Because You Want To or Are You Afraid Not To?

Fear, Lum said, is a terrible reason to keep working. Being afraid you won’t have enough money, even if your accounts say otherwise or fear of being bored even though you have lots of hobbies you’re planning to try out.

Suffering from too much analysis paralysis often leads to making no decisions at all. Instead, you keep working and wind up working longer than you need to.

Lum recommended asking yourself: “If money wasn’t an issue, would you keep working?”

If you answer yes, it’s likely because you love what you do and it gives you a sense of purpose. But if it’s no, why are you continuing to work?

This article was provided by MoneyLion.com for informational purposes only and should not be construed as financial, legal or tax advice.

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Written by

Heather Taylor

Edited by

Rebekah Evans