Joshua Winston, who’s 70, thought he had retirement all figured out. He ran two thriving veterinary clinics, made some savvy investments, and kept his spending in check.
But just a week after he hung up his stethoscope for good in May, he found out he had cancer. Now, looking back, Winston wishes he hadn’t spent so many hours working and had instead enjoyed more trips and date nights.
He’s among a handful of people who shared their thoughts in an informal Business Insider survey about how they feel they worked too hard or focused too much on saving for retirement at the expense of family time and fun when they were younger.
This is part of a larger series that includes insights from over 3,600 older Americans who’ve opened up about their regrets through surveys or emails to reporters.
Some respondents felt like they were lagging behind on their retirement goals and opted to skip out on big purchases only to realize later that they were actually well-prepared but just overly cautious.
A few mentioned that tough experiences—like losing a loved one or facing serious health issues—made them anxious about having enough savings for emergencies down the line. Conversations with five individuals who believed they were too frugal shed light on the challenges of planning for retirement effectively.
Dylan Tyson from Prudential Financial summed it up nicely: “When you’re an oversaver, you hold back from enjoying life—like skipping that extra trip or concert with family and friends—because you’re worried you might not have enough saved.”
Preparing financially for a lackluster retirement.
Winston, a resident of Arizona, dedicated a significant portion of his career to veterinary medicine. Over the years, he drove simple cars, lived in a comfortable upper-middle-class home, and was careful about making big purchases.
By the time he retired, he had saved around $3 million but regretted not spending some of that on hiring an assistant for his practice. This would have spared him from working late nights answering calls for an emergency vet hotline. It really drained my energy, Winston shared.
Whenever I went out with my wife to watch a movie, I’d get bombarded with calls. He did recognize that the helpline contributed to his practice’s success, though.
He intended to use some of his savings during retirement but received a lung cancer diagnosis in May and described life since then as “hell.”
I’ve got enough money to live comfortably until I’m 95 and even take vacations, he said sadly. I thought I had my whole life ahead of me, and now this is what I’m facing—cancer—and I might not even get to enjoy the money I’ve worked so hard for.
Tyson chimed in on retirement planning, noting that while much of it involves educated guessing, it’s crucial for people to figure out how much income they’ll need throughout their lives to meet their retirement goals while balancing what they want and need financially.
With so many Americans dealing with uncertainty these days, Tyson explained, “we’re seeing savvy individuals taking proactive steps by creating financial plans focused on what truly matters most to them.”
He emphasized that by securing reliable income sources for their retirement needs and desires, people can worry less and focus more on pursuing their dreams.
Putting in excessive hours and neglecting relationships with friends and family.
Ruth Mills, 63, shared that she started saving a bit later in life but managed to build a nest egg of over a million dollars through living simply and investing wisely.
Living in Minnesota, she had kids when she was just in her early 20s, which made money pretty tight. As a single mom, Ruth juggled multiple jobs—she worked as a part-time personal care assistant on top of her full-time job. Eventually, she climbed the ladder to become a senior accounting officer for the state.
Because she was so busy working and raising her kids solo, she missed out on chances to hang out with friends or travel more with family. Looking back, she wishes she’d spent a little less time saving and maybe worked one less job or pursued some hobbies instead.
I did manage to save for retirement well, Mills reflected, but I was perhaps too frugal and didn’t enjoy my younger years as much because I was always working. She mentioned postponing a trip to Ireland that now feels out of reach physically.
Recently, Ruth downsized her home and is looking forward to retiring soon so she can spoil her grandkids and lead an active lifestyle. Having all the money in the world would be nice—though I don’t have that—but if you end up alone without friends or loved ones to share it with at the end of the day, what’s the point? Mills said.
She added that after making sacrifices for savings and investments earlier on, she’s excited about achieving financial security that allows her to cover life’s essentials while creating memorable experiences with her grandchildren.
Ryan Viktorin, a financial consultant at Fidelity who holds a CFP designation, noted that there are three types of “oversavers.”
Some people face unexpected events that prevent them from spending their savings; others worry they won’t have enough due to healthcare costs or market fluctuations; and then there are those who keep working because they haven’t mentally transitioned into retirement yet—they fear it might feel dull or isolating.
She mentioned that many baby boomers retiring today were raised on tales from their parents or grandparents about the Great Depression.
I often hear from clients who have done a great job saving, but they feel this deep-rooted urge to stay frugal. It’s like they can’t fully enjoy life because they’re so focused on saving, she shared.
Not being present for important family events.
Kirk, who’s 75, admitted he didn’t realize how well he was setting himself up for retirement. This retired attorney from California, preferring to keep his last name private, worked with various financial institutions and fully funded his 401(k).
As a result, he built up over $1.1 million in tax-deferred savings for retirement. Still, he worries that an unexpected emergency or a market downturn could throw a wrench in his plans for a relaxed retirement.
After stepping away from his full-time job at 67, Kirk recognized that he had let some opportunities slip by because he was too cautious with his spending.
He wishes he had taken that long trip to France with his brother during his 60s; unfortunately, now his brother faces cognitive challenges that make traveling tough. On another occasion in Hawaii, even though he paid for a helicopter tour for his two kids, Kirk opted out himself just to save some cash.
“It would have been such an amazing experience to share with them—something we could have reminisced about forever,” Kirk reflected. “Now I could afford a dozen helicopter rides without it making a dent in my finances.”
Viktorin emphasized the importance of examining the balance between income and expenses to find some flexibility in your budget beyond just saving for retirement; this can help ease some of the worries many older Americans face.
“When you create a financial plan,” Viktorin noted, “you can explore different scenarios and see how they pan out. What if we took an extra vacation and spent a bit more? What if we chose business class instead of economy? What if we started supporting our kids financially more?”