Meet the oversavers: Older Americans who have plenty for retirement but wish they'd worked less and vacationed more

• Some Americans "oversave" for retirement and end up sacrificing during their working years.
• Financial planners advised balancing savings with enjoying life to avoid regrets in retirement.
• This is part of an ongoing series on older Americans' regrets.

Joshua Winston, 70, did a pretty good job preparing for retirement: He ran two successful veterinary clinics, made smart investments, and lived frugally.

But a week after he retired in May, he was diagnosed with cancer. Now, Winston said, he regrets working such long hours during his career, often missing out on trips and date nights.

Winston is one of a few dozen respondents to an informal Business Insider survey who said they worked too hard during their careers or focused too much on saving for retirement, sacrificing family time, travel, or other leisure activities when they were younger. They're among the more than 3,600 older Americans who shared their life regrets through surveys or direct emails to reporters. This story is part of an ongoing series.

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Some survey respondents thought they were behind on retirement goals and chose to bypass larger purchases, only to realize they were well-prepared and too cautious about getting there. A few said traumatic experiences, such as the death of a loved one or a catastrophic medical diagnosis, made them anxious about saving money in case of another emergency. Interviews with five Americans who thought they were too frugal point to the difficulties of knowing how to best prepare for retirement.

Dylan Tyson, the president of retirement strategies at Prudential Financial, described the mindset of an oversaver: "You're cutting back on living — not taking that extra trip or going to that concert or ball game with family and friends — because you're worried that you don't have enough saved."

Saving for an anticlimactic retirement

Winston, who lives in Arizona, spent much of his career in veterinary work. Throughout his life, he drove modest vehicles, lived in an upper-middle-class house, and was cautious about making larger purchases.

He retired with about $3 million but wished he'd spent some of that money on an assistant for his practice so he wouldn't need to work nights running an emergency vet helpline.

"That sucked up a lot of oxygen in my life. I never could watch a movie when I went out with my wife because I would get a dozen phone calls," Winston said, though he acknowledged the helpline helped make his practice successful.

He planned to spend some of his savings in retirement, but he was diagnosed with lung cancer in May and said life has "been hell" since then.

"I have enough money to live until 95 and go on vacations. I have a whole life ahead of me, and this is what happens," Winston said. "I have cancer, and I may not even enjoy the money I worked hard to save."

Tyson said that while a lot of retirement is "guesswork," people should try to determine how much lifetime income they'll need to achieve their retirement goals while balancing their spending needs, wants, and wishes.

"With millions of Americans facing uncertainty, we see the smartest of them taking action to create financial plans that focus squarely on the things that matter most," Tyson said. "Then they are protecting those goals by ensuring that they have secure, predictable income to fund their retirement needs and wants — freeing them to worry less and pursue their greatest wishes."

Working too hard and missing out on friends and family

Ruth Mills, 63, said she began saving later in life but amassed seven figures through frugal living and careful investing. The Minnesota resident had children in her early 20s and finances were tight. As a single mom, she held multiple jobs, working odd jobs as a part-time in-home personal care assistant in addition to full-time work. She worked her way up to a senior accounting officer for the state.

She said because she worked so much and cared for her children alone, she missed opportunities to go out with friends or travel more with family. She said a part of her wished she'd forgone some savings so she could have worked one less job or had hobbies.

"I did well saving for retirement, but so much so I was too frugal along the way and did not enjoy as much while younger as I worked too much," Mills said.

Mills said she pushed back a trip to Ireland that she's no longer physically equipped to take. She recently downsized her house and hopes to retire soon and use her retirement years to spoil her grandchildren and have an active lifestyle.

"Having all the money in the world is great, and I don't have that, but if you don't have the friends and people to spend it with at the end, it's a trade-off," Mills said. She added, "Having made the necessary sacrifices to save and invest earlier, I am looking forward to having the financial security to be able to afford the basic necessities and share adventures and experiences with the grandkids."

Ryan Viktorin, a financial consultant and CFP at Fidelity, said she sees three categories of "oversavers": people who experience an unfortunate event that keeps them from spending the money they've saved, people who worry they'll never have enough because of healthcare costs or market volatility, and people who continue working because they haven't mentally prepared for retirement, fearing it's monotonous or isolating.

She also said that baby boomers retiring now grew up hearing stories about their parents or grandparents going through the Great Depression.

"Sometimes I hear from my clients who have saved really well who say it's in their bones to continue to be frugal, and they feel like they can't really enjoy themselves or live their lives because they have to keep saving," she said.

Missing out on key family moments

Kirk, 75, said he didn't realize he was doing such a good job of preparing for retirement. The retired California attorney, who asked to use only his first name for privacy concerns, worked for various financial institutions and maxed out his 401(k). He amassed over $1.1 million in tax-deferred retirement savings. However, he feared an emergency or market crash would derail his plans for a comfortable retirement.

After retiring from his full-time job at 67, he realized there were opportunities he missed out on because he held back on spending. He regrets not going on a weekslong trip to France with his brother in his 60s; now, his brother has cognitive challenges that make travel difficult. On a trip to Hawaii, he signed his two children up for a helicopter tour but didn't go himself to save money.

"It would have been a great experience to have shared with them and talked about for years to come," Kirk said. "I could now pay for a dozen helicopter rides and not miss the money."

Viktorin said it's important to look at the gap between expenses and income and figure out where there's some wiggle room in your budget beyond saving for retirement, which may help alleviate some of these anxieties older Americans have.

"When you build out a financial plan, you can build out the 'what ifs' and see what it looks like," Viktorin said. "What if we took an extra trip and spent more money? What if we flew business class rather than coach or economy? What if we started to help our children more?"

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