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7 Big Retirement Surprises and What to Do About Them

Try these tips to navigate retired life’s unexpected twists and turns


spinner image a woman opens a box full of surprising items
Jan Buchczik

Retirement is supposed to be that time of life when the sun shines golden, the vacation has no expiration date and the early-bird dinner deals are endless.

All those expectations might come true. Inevitably, though, retirement will spring something unexpected on you.

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Some of these surprises are good. Some are not so good. Either way, it’s best to be as ready as you can be for whatever retirement throws at you.

To that end, we asked four authorities who have written books on retirement lifestyle and finance to weigh in on the surprises they hear about most and how to avoid them if you can — or deal with them if you must.

1. Surprise! Leisure gets boring fast

People who retire in a position to bask in leisure 24/7 often discover something they never expected: Leisure can be a yawner.

“Sure, every day is Saturday, but what do you do — mow your lawn every day?” asks Mitch Anthony, a consultant to financial advisers and author of The New Retirementality: Planning Your Life and Living Your Dreams at Any Age You Want.

“When people only have leisure, they find out it’s not so fun anymore,” he says. And once retirees stop having fun, they can get pessimistic and hit a downward spiral.

Anthony cites a retired friend, formerly an engineer at IBM, who played golf every day for five months with four buddies, all also recently retired. They drove each other crazy. Anthony says his friend couldn’t take having “the same conversation over and over with the same results every day.“

Solution: Get a life. Anthony’s buddy soon got a part-time job as a limo driver. He didn’t really need the money, but he needed a purpose beyond hitting the links every day.

“You need a vacation and a vocation,” Anthony says. “The two feed off each other. When you have something meaningful to do every day, it makes the leisure stuff fun.”

2. Surprise! You can’t stop checking your portfolio

It’s one thing to review your 401(k) statement when it shows up in the mail or online. It’s something else entirely to be on your laptop for hours a day, tracking your portfolio’s every microscopic movement.

This is your inner fear of running out of money in retirement rearing its head, Anthony says. Many retirees share this fear, and too much free time only makes it worse. These are the retirees who obsess over the stock ticker on CNBC and endlessly watch the financial news shows.

“They should be investing in Pepto-Bismol, because they’ll be drinking more of it,” he says.

Solution: Don’t retire before you feel financially ready. Most folks underestimate how strongly they will feel about getting their last paycheck, Anthony says. Going forward, “your income is pretty much set. Your expenses are not going to be set. Taxes don’t go down. Costs don’t go down.”

spinner image a person looks distressed as shapes and arrows emerge from their laptop
Jan Buchczik

The best defense against portfolio obsession is to retire only when you’re financially comfortable in your retirement shoes. And not just for your own fiscal sanity, he says. That constant checking “drives your [financial] advisers crazy, too.”

3. Surprise! The kids come back (or the folks move in)

In family life, stuff happens. This is the one retirement surprise that should never be a complete surprise. Whether it’s your adult kids returning to the nest after graduation, a job loss or divorce or your parents moving in for health or financial reasons, it’s critical to be prepared for the possibility, says Jason Parker, president of Parker Financial in Silverdale, Washington, and the author of Retirement Calculator: How Much Money Do I Need to Retire?

Solution: Roll with it. Some retirees genuinely love it when a kid moves back in, especially when grandchildren are part of the bargain. “They get not only more time with their grandkids but supper with them every night,” Parker says.

If space under your roof is tight and the multigenerational household seems like a long-term thing, you might consider adding a so-called accessory dwelling unit (ADU) on your property, provided your city or county permits it and you have the means. These small, detached dwellings on your property typically cost from $60,000 to $225,000, depending on size, according to online home-services marketplace Angi.

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4. Surprise! Your first-year spending is through the roof

Plain and simple, most people spend more in the first year of retirement than they ever expected to, says Parker. That’s especially true with prices for many products continuing to rise, albeit at a slower pace than during the inflation spurt of 2021 and ’22. And some costs have kept on spiking: In 2023, the average U.S. rate for car insurance jumped 24 percent compared to 2022, according to Insurify, an insurance comparison shopping site.

But even when inflation is tame, discretionary spending tends to rise in early retirement as folks newly freed from the workaday grind indulge more in things like travel, entertainment and eating out. Parker estimates that people spend 10 to 20 percent more on discretionary items in their early retirement years than they expected to.

Solution: Make a realistic budget. Most folks retire without closely comparing what they want to do with how much it will cost to do it. Building a comprehensive spending plan is a great way to avoid digging yourself into a hole, especially if you can do it with the help of a financial planner, Parker says.

Don’t just add up regular fixed bills like rent, utilities, insurance and taxes — factor in travel and entertainment, too. Err on the side of overestimating rather than underestimating your discretionary spending, Parker advises. If your retirement income doesn’t cover it, you’ll need to be more realistic about your spending (or find a way to bring in more money, like gig work or a part-time job).

5. Surprise! You and your spouse approach retirement differently

If you are married or have a significant other, remember that retirement is not a single decision, says Patrice Jenkins, an organizational psychologist and author of What Will I Do All Day? Wisdom to Get You Over Retirement and On With Living! “If you are in a committed relationship, deciding to retire needs to be a conversation,” she says.

Retirement means that you and your spouse suddenly face the daunting prospect of spending up to 40 extra hours each week together, Jenkins notes. Failing to communicate in advance about how you each envision your retirement years will likely lead to disagreement and disappointment, she says.

Solution: Plan time to be together, and apart. Too much time apart in retirement is not a good thing, Jenkins says, but neither is too much time together. Plan your months, weeks, even days around doing both things you can share and things you each want to do on your own.

“You need a ‘your time,’ ‘my time’ and ‘our time’ plan,” she says. Identify your individual interests as well as those you share as a couple and, critically, give each other time and space to pursue them.

6. Surprise! You have a harder time spending than saving

For many folks, one of the most difficult adjustments in retirement is suddenly flipping the switch from years and years of saving money to years and years of spending money. “It’s really hard to transition from being a saver to spending and seeing your account balance going down,” says Jenkins.

Solution: Trust the plan. Just as creating a budget can help forestall overspending at the start of retirement, developing a solid financial plan can show you when, and how, you can afford to do the things you want to do.

Parker recalls advising a well-to-do retired couple who had long dreamed of taking a 30-day cruise. “The husband really wanted to do this, and the wife thought they couldn’t afford it,” he says. Parker printed out the details of their financial plan to demonstrate that they could.

“It was a dream come true. They would never have taken it if I hadn’t told them it was OK,” he says. “Have a good financial plan so you know that you can spend.”

7. Surprise! You live longer than you thought

Most people expect to die sooner than they do, says Teresa Ghilarducci, a professor of economics at the New School in New York City and author of Work, Retire, Repeat: The Uncertainty of Retirement in the New Economy. That can lead them to plan and save for fewer years of retirement than they’ll have, increasing the risk of outliving their money.

An August 2023 report by financial services company TIAA and the Global Financial Literacy Excellence Center at George Washington University documents Americans’ low “longevity literacy.” Only about a third of U.S. adults they surveyed correctly answered multiple-choice questions about the average life expectancy for a 65-year-old (84 for a man, 87 for a woman) or the probability of a 65-year-old living to 90 (about 30 percent for men, 40 percent for women). Most of the incorrect answers were either “don’t know” or underestimates.

Many people base their expectations on how long their parents or grandparents lived rather than on data, Ghilarducci says. The fallout can be particularly acute for married women, she adds.

“Most married couples spend as if the wife will live just a little bit longer than the husband,” but the gap is often considerably longer, she says. “The surprise is, the widow or divorced woman will [have to] live with a lot less money than the couple thought.”

Solution: Do the research — then overestimate. Retirement security rests largely on building a financial cushion that lasts as long as you do. No one knows exactly how long they’ll live, but there are resources to help you get a better sense of the probabilities and plan accordingly.

One valuable step is to search out actuarial data, like the life tables published annually by the National Center for Health Statistics. Find the average life expectancy for your current age and plan as if you’ll live five years longer, Ghilarducci suggests. That can give you, and your spouse, an extra measure of confidence that your money will last as long as you do.

Another resource is the Actuaries Longevity Illustrator, a tool developed by the American Academy of Actuaries and the Society of Actuaries that estimates the probability of your living to various ages based on your age, gender and overall health. You can also enter information for your spouse to help determine how long you can reasonably expect to live as a retired couple.

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