19 March 2026

4 Big Retirement Questions

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The questions that workers grapple with as they look ahead to retirement range from the financial to the philosophical. Some lend themselves to straightforward answers: Yes you can—or no you can’t—afford to keep your vacation home as well as your primary residence. Others are more open-ended and may take years of trial and error to resolve.

Here are four questions that loomed large in two focus groups that research firm Hearts & Wallets conducted in New York last week with people ages 53 through 70 who indicated they were at least five years away from stopping full-time work.

What’s the Goldilocks age for me to retire? Many workers are fearful of quitting—or getting pushed out of the workplace—before they have enough money to live comfortably for the rest of their days. But there’s also concern about waiting too long and missing the sweet spot when they still have the physical ability and good health for the activities on their retirement wish list.

Should I buy long-term-care insurance? Whether in a nursing home, assisted-care facility or at home, extended care can be a retirement budget-buster. But long-term-care policies aren’t necessarily the answer. The premiums can be thousands of dollars a year—and insurers have been hiking charges for people who bought long-term-care insurance years ago.

When should I collect Social Security? Depending on a person’s year of birth, there’s an age at which he or she will get “normal” or “full” benefits based on a career-long work record. But really, it’s a continuum: People can collect retirement benefits as early as age 62 or delay to age 70, with the monthly check getting bigger the longer they wait.

One man of 66 said he has started collecting because he wants the money now and would rather invest it himself than wait to get a larger monthly check. But other panelists said they have heard conflicting advice and are confused about when to collect.

Unlike some other big retirement questions, the decision about when to start Social Security lends itself to a straightforward analysis based on assumptions about life expectancy, marital status and other factors. There are a variety of paid and free online tools that can be helpful.

Who will the “retired me” be? While the thought of having too little money for retirement is scary, so too is the question of how to spend one’s time and maintain a sense of purpose and identity.

“I enjoy working,” including the experience of working with younger colleagues, said one man of 54. He is thinking he may transition from full-time to part-time work in about five years.

A woman who is 66 said many people spend more time planning their summer vacations than planning what they are going to do when they retire. She and her husband are laying the groundwork for a retirement that may start in another five years.

 Click here to access the full article on The Wall Street Journal.

 

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