Wealth management
Three quirky retirement questions everyone should be asking
Americans spend too much time thinking about bucket lists and not enough about what their daily lives will be like in retirement, one expert says.
Summary
- Pre-retirees pay too much attention to planning for travel in retirement and not enough time planning for their daily lives.
- Consider a retirement test drive. Explore public transportation to determine whether remaining in your home without a car is feasible. Experiment with handyman apps so you’ll know your options when your DIY days are done.
- Loneliness is a common problem in retirement. Be proactive about making and keeping friends in the years leading up to your retirement.
Rethinking retirement beyond travel
When workers 50 and older were surveyed recently on what they expected to do in retirement, the most common response was “travel.” A whopping 65% of pre-retirees said they envisioned a retirement filled with planes, trains, campers and cruise ships.1
Joseph Coughlin, a leading expert on aging and the director of the MIT AgeLab, doesn’t particularly like this answer—and it’s not because he’s some kind of curmudgeon. The affable, bow-tied professor enjoys a good vacation as much as the next person. He’s just quick to point out that only a fraction of our retirement years are spent strolling with giant tortoises in the Galápagos, touring thousand-year-old temples in Tokyo or doing anything else on our retirement bucket lists.
“Wealthy retirees travel only one month a year,” says Coughlin, also a TIAA Institute research fellow. “If you’re super-wealthy and have your own boat, maybe it’s two months. Question is, what will you do with the rest of your time?”
According to Coughlin, planning a happy, healthy retirement requires less focus on the fabulous and more on the mundane. Less focus on how much fun you’ll have at Disney with the grandkids and more on how you’ll get to the airport. With this in mind, Coughlin has crafted three quirky questions designed to get people thinking about everyday life in retirement.
Question #1: Who will you have lunch with?
“You spend more time socially with the people you work with than the people you live with,” says Coughlin. “If you retired on Friday at 5 o'clock, you left a big part your social portfolio at work. So on Monday, who are you going to have lunch with?”
One in three adults ages 50 to 80 report feeling lonely or isolated.2 Making and keeping friends gets harder with age, so the purpose of Coughlin’s lunch question is pushing people to be more proactive about socializing. The most common answer is a spouse or partner, but as we all learned during lockdowns, together time has its limits. “Covid was actually a fire drill for retirement,” Coughlin says. “It turned out your significant other did not enjoy seeing you 24/7, 365 days a year.”
What does being proactive look like? “Have you thought about connecting with old friends and rekindling those relationships?” Coughlin says. “Have you considered taking a class, not necessarily to learn but to connect with others? And you know those hobbies you want to do? Don’t do them alone.”
If you enjoy bird-watching, in other words, join a birding group. If you like gardening, volunteer at a community garden. “Get out there and do it with other people,” Coughlin advises.
Question #2: Who’s going to change your lightbulbs?
Falling is a major risk for seniors. Twenty-two percent of seniors who suffer hip fractures die within a year of the injury.3 Of those who recover, a majority never regain full independence.4 So while Coughlin’s second question may sound silly, it’s actually quite serious.
“As we age, we become less well physically,” says Coughlin. “Our balance on that ladder is not quite as good as it used to be.”
“So the question then becomes, who are you going to find and trust to go into your home and help you do all those things you now take for granted, like changing light bulbs, taking out the trash, cleaning the gutters or whatever it might be?”
A 60-year-old couple in good health isn’t thinking about such things. Nor are their children. But they should be. “Don’t wait until there’s a crisis,” says Coughlin. If your children won’t be nearby to help, see if there’s a friend or neighbor who could. Another suggestion: Experiment with on-demand services, such as handyman apps or grocery delivery apps. “That way,” he says, “they won’t be novel when you need them.”
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Question #3: How are you going to get an ice cream cone?
Coughlin’s final question addresses the mobility challenges of older age. “It’s a hot summer night,” he hypothesizes, “and suddenly you have the desire—or at least I always do—for a soft-serve ice cream cone. How are you going to get it?” For most pre-retirees, the answer is obvious: You’ll grab your keys, get in your car and dive to your favorite ice cream shop. But what happens when you’re 80 and don’t like to drive at night—or maybe can’t drive at all?
As with the light bulb question, Coughlin encourages people to experiment. Explore local bus routes or take an Uber when you don’t have to. It will make the transition to post-car life easier. “You're not going to suddenly say, ‘Gee, I don't feel well enough to drive, and even though I haven't used the bus for 50 years, today is the day I'm going to take the bus to Dairy Queen to get ice cream!’”
Another consideration is location. Coughlin says 70% percent of older Americans live in suburban or rural areas where the inability to drive diminishes quality of life. For many, an apartment in a city or town center will be a better retirement choice than a suburban home. Not only will they be able to walk to their favorite ice cream shop (or bakery or bookstore), but they’ll also have fewer stairs to navigate, assuming the building has an elevator.
“You want a community that has all the things that make you smile and keep you vibrant but also has them close enough so it’s not a big project to get there,” says Coughlin.
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1Transamerica Center for Retirement Studies, “Life in Retirement: Pre-Retiree Expectations and Retiree Realities,” September 2023,
2Institute for Healthcare Policy and Innovation, National Poll on Healthy Aging, University of Michigan, “Trends in Loneliness Among Older Adults from 2018-2023,” March 2023,
3Downey C, Kelly M, Quinlan JF. Changing trends in the mortality rate at 1-year post hip fracture - a systematic review. World J Orthop. 2019 Mar 18;10(3):166-175. doi: 10.5312/wjo.v10.i3.166. PMID: 30918799; PMCID: PMC6428998,
4Dionyssiotis Y, de León AO. Sarcopenia and Hip Fractures. J Frailty Sarcopenia Falls. 2024 Mar 1;9(1):1-3. doi: 10.22540/JFSF-09-001. PMID: 38444544; PMCID: PMC10910255,