Older Americans who have plenty for retirement but wish they’d worked less and vacationed more


Man looking out.
Americans who oversaved for retirement told BI they wish they’d spent more time and money on experiences with loved ones.Getty Images; Jenny Chang-Rodriguez/BI
  • 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.”

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.

Joshua Winston
Joshua Winston said he missed out on some opportunities for leisure because of his work schedule.Joshua Winston

“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.


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