Retired boomers have one big regret

Ron Sherman has always had what he considers a typical baby-boomer attitude toward work: You’re loyal to your employer, you give 100%, and you never call out sick unless you really have to — and even then, you might try to push through anyway.

Work, however, has not always had that same attitude toward him. Sherman has been laid off three times in his career: once after his company was bought out, once after his job was shipped overseas (he trained his replacement), and, most recently, after his team at a major cable company was downsized. “Three strikes, you’re out,” he somewhat painfully jokes. The company says age has nothing to do with it and that it was about title, but Sherman, who is 67, notes that everyone who was cut from his team was over 60. As he contemplates whether it’s time to retire, the callousness with which his past employers treated him is making him rethink his give-it-all-on-the-job attitude.

“I was sort of raised that you do a hard day’s work and you’re honest, and things will work out for you — it’s a two-way street between you and your employer,” he says. “But I found out that’s truly not the case.”

Sherman and I talked after he saw a story I wrote about Gen Z taking more time off of work — the HR platform Dayforce found a 55% increase in sick leave from 2019 to 2023, with the biggest jump coming from the under-35 crowd. Maybe the youngs have the right idea, he thought, and workers should take the time they have when they have it. Sherman built up 360 hours of sick leave at his last gig that went poof when he was let go — he wasn’t credited or even paid out for it.

People have strong feelings about missing work. After publishing the article about Gen Z’s predisposition to take time away, I got a lot of feedback from older generations. Some of it was predictable “the kids these days” complaints lamenting that nobody wants to work nowadays, that work ethic has disappeared, etc. But other comments struck a different note. People talked about respecting and even admiring Zoomers’ willingness to lean out. Some even expressed regret at how much they’d given up in service of The Man, who, in retrospect, was in a one-sided, neglectful relationship with them.

American work culture hinges on the idea of the ideal worker — someone who goes above and beyond, who’s always available, whose life outside the office the higher-ups pay no mind to. It leads to some unhealthy behaviors, like presenteeism, where employees go to work even though they’re not well, and it’s the reason employees wind up on a quiet vacation rather than a real one. It’s not a great system, but it’s one that workers have for decades bought into. It’s also creating people who are left wondering later in their careers or in retirement if all that energy they put toward their jobs was worth it.

“I wonder how many young millennials and Gen Z are hearing remorse from their boomer parents for having sacrificed their health for the sake of a job,” said David Johnston, who retired from his job at a utilities company in 2020. He says he often warns his daughter and her cousins not to let work “wreck their health.” Johnston is well aware of the stakes — he got a cancer diagnosis on his first day of retirement. “I was like, ‘You’ve got to be kidding,'” he said. “It’s like a story you couldn’t make up.”

He’s fine now, but looking back at his decades in the workforce, he thinks about how much time he lost traveling for work or just going to and from the office. He spent two to three hours a day commuting, and over 40 years, that adds up. (That’s why he thinks this remote work thing sounds good, too.) Johnston is Canadian, and he figures at least he didn’t have it as bad as his American counterparts, who he said were great to collaborate with because they worked so hard but also had a work ethic that was “nuts.” He’s proud of what he accomplished, but he wishes he’d spent more time with his daughter. “My father did the same thing, so for me, it wasn’t that big of a change,” he said. “It was almost normal.”

There’s got to be work-life balance, and I didn’t have work-life balance.

Dave Kotwitz, who worked for and then owned a Piggly Wiggly grocery store in Wisconsin, expressed a similar sentiment about missing out on watching his kids grow up. (I’ll disclose here that I know Kotwitz — I went to school with his daughter, and his Pig was my Pig.) When he started out as a manager, he worked open to close for two years, and even after he became the owner, a 40-hour workweek was a rarity. The time suck wasn’t just the store; his involvement in the community — the local chamber of commerce, etc. — ate up hours, especially in the evenings. His daughter brings up things that happened when she was growing up, and he doesn’t have any recollection of them. He has no memory of her being on the golf team in high school, for example. “I was pretty much buried in work,” Kotwitz said. “There’s got to be work-life balance, and I didn’t have work-life balance.”

In his retirement, Kotwitz has been doing more yardwork and taken up beekeeping and blacksmithing. He wishes he’d gotten into those a long time ago — they would have been more fun when he had more energy.

Not everyone I talked to for this story was so sold on the idea of relaxing on the job. There was Charlie Stuart, a documentary maker who retired in 2020 and then, after realizing he didn’t want to play golf three days a week, decided to get his real-estate license. He’d spent most of his career working for himself, which is a blessing and a curse. You can make it to your kid’s 2 p.m. baseball game, but that’s because you can go back to work at 10 at night. “When you work for yourself, you’re working for one of the biggest jerks you’ve ever worked for,” he said.

David Vequist, a management professor in Texas, is happy with where he ended up, but he admires that his Gen Z students seem to prioritize their side gigs and passion projects over their day jobs. Paul Miola, who spent his career working in insurance and is now mostly retired, didn’t need to wait to learn a lesson about the value of time off. Forty-five years ago, he took some days off to help his wife care for their first child, and when he returned to work, his manager told him it would affect his performance review. “It shocked me. Like, really?” he said. “But that’s the way things were then.” When Miola started managing people, he made sure to do things differently.

Among younger generations — say, Gen X and below — there’s a sense that they don’t want to repeat their parents’ mistakes, workwise.

One thing I will note here is that I talked to a lot of men for this story. While boomer women worked more than their own mothers did, they were not employed at the same rates as Gen Xers and millennials. In many boomer families, it was the expectation that the woman deal with childcare needs. If she was working, her boss may have been more understanding, too. The people I talked to were also generally more affluent, the types for whom the hard work had paid off. I wonder if there’s more space for reflection there than there is for, say, single parents or blue-collar workers who feel they didn’t have a choice in their approach to work. They needed to put bread on the table and support their families, and that was that.

Chris Woods, a financial advisor who founded Silvis Financial, based in Charlotte, North Carolina, spends many of his days talking to pre-retirees thinking about their future and rethinking their past. No one ever tells him they wish they’d worked more, though many wish they’d invested more. Some say they wish they’d changed careers earlier on to improve their quality of life. Among younger generations — say, Gen X and below — there’s a sense that they don’t want to repeat their parents’ mistakes, workwise.

“If you had boomers as parents, then you grew up watching them work eight-plus hours a day five days a week for 40 years, and maybe they didn’t spend as much time with their kids,” Woods said. “I think a lot of people have seen that and they want to do it differently.”

Yes, people want to arrive at retirement with enough money in savings, but there’s more to the equation. They want to make sure they capitalize on that time, whether by traveling or spending time with family or taking up hobbies or whatever else. They want to get there in good health so they can actually enjoy it all, and that’s not guaranteed, especially in a work culture that has historically pushed people to run themselves ragged.

Candidly, it’s something I think about a lot. I have very much internalized the capitalist machine and have a tendency to overwork. As much as I tell myself it’s fine to just be fine, my default setting at work is often sprinting. I cannot remember the last time I called out sick, even when I probably should have. And I worry that in 30 years I’ll be set to retire and I’ll wonder if everything I’m putting in now was worth it. That’s assuming I’ll get there, which, who knows. If Gen Z is easing off the gas pedal a little bit, maybe I should, too.

None of the boomers I talked to was in favor of people calling out of work willy-nilly. They pointed out that it’s a strain on colleagues who are expected to pick up the slack and that it might ultimately come back to bite you. A couple also suggested that if a young worker is missing work so much — because of the stress, or maybe because they just hate it — it’s probably time to look for a different job. If you’re in your 20s and you don’t like the track you’re on, it’s a whole lot easier to jump to a different one now than in your 50s.

Still, there’s more to life than work, and if younger people are seeing that, I mean, great. It’s hard to imagine being 75, sitting on your porch, and wishing you’d put in more overtime.