White-collar baby boomers are facing a dilemma: Embrace AI or retire early

Keith Hayden, a 53-year-old software engineer, started searching for a job last fall.

He soon realized interviewers had AI top of mind, and Hayden, who has already adapted to big innovation shifts over the past two decades, didn’t have the best answers.

So he bought a Claude subscription and started to learn more.

He knew he had to adjust — AI is rapidly shifting how software engineers work — as he’s not in a financial position to retire early.

After some experimenting, he says he’s “optimistically skeptical” about AI’s ability to write code well, but hopes there’s still space for him to write code in the new era, because he doesn’t just need to work, he loves it. “I’m one of those weird people who enjoys the code,” he says. “Letting some AI do it for me takes the fun out of it a little bit.” Hayden is among the Gen Xers and Baby Boomers who spent decades honing a craft, climbing the career ladder, and hoping to bow out of the workforce on their own terms.

They thought they had the corporate world figured out — then came the AI revolution.

While 58% of adults under 30 reported ever having used ChatGPT, just a quarter of those ages 50 to 64 said the same as of early 2025, according to a Pew Research Center survey.

Some older workers have opted for early retirement rather than holding on and waiting for their roles to become redundant or navigating the office upheaval bosses promise AI will bring.

But many others want or need to stay employed.

The proportion of workers older than 55 grew from 10% in 1994 to 25% in 2022, according to U.S.

An AARP survey last fall found that 7% of people who left the workforce unretired last year amid economic uncertainty, while other retired people dabble in AI-fueled hobbies with their free time.

About half of Baby Boomers in the workforce said they use AI, according to a London School of Economics survey.

So far, it’s the AI-native, recent grads who are struggling the most to land jobs.

As AI lops off the bottom rungs of career ladders, workers with more experience prove valuable for their decades of expertise and ability to discern the usual output from the slop AI also produces.

But it often means having to learn the new ropes to keep, or get, a job, and beating ageist stereotypes and looming layoffs that often disproportionately affect higher paid, older workers. “This is the first time I have seen a technological innovation benefit older workers more than younger workers in terms of job security,” says Heather Tinsley-Fix, senior advisor of employer engagement at AARP. “All of that deep experience and expertise in a specific profession — but also in those soft skills of critical thinking and understanding at a systems level what’s happening — those are skills that older workers tend to have.” Opportunity calls for Gen Xers and Boomers to win in the AI era, but they’re staring down a clock to retirement that competes with companies’ amped up races to automate much of white collar work.

Few people live to work or work to live — most fall somewhere in the middle, especially as they ponder retirement.

They need their retirement portfolios in order, but also want to have an anchoring purpose in society.

An impending societal shift can lead them to wonder if they would rather make that impact inside an office or elsewhere. “Big changes in general, such as COVID, they have a lot of us asking, ‘well, what’s the meaning that we are deriving from work, what do I want for my future?

Is this really what I want to be doing?'” says Daniel Jolles, a behavioral scientist at the London School of Economics and Political Science. “AI is forcing people to ask a lot of those same questions.” Some left high-risk jobs during the peak of the pandemic for fear of getting sick or decided they wanted to retire after working from home.

About 1 million more people retired than expected in 2020, but many were pushed out of the labor force after long-term unemployment, according to the The Schwartz Center for Economic Policy Analysis at The New School. “The worst outcomes for retirement come when people are forced to retire unexpectedly,” says Jolles.

For older workers on the job search, that fear is palpable.

Stacy Gilchrist expected to stay in her former healthcare management role until she retired.

But she’s been looking for a job for the past two years following a layoff, and now 57, she had to learn new rules for a changing hiring game, eventually hiring a career coach to help her.

She’s done contract work for an AI healthtech company, training an AI agent to ask questions a nurse would.

There are some new opportunities with AI, but it has also created new obstacles for her to navigate in the job application process. “I call them shenanigans,” she says.

Despite their frustration, older workers are not rebelling against AI like recent grads.

A recent Gallup poll found Gen Z feels increasingly anxious and angry about AI.

A Quinnipiac University poll found that Gen Z and Millennials were more likely than Gen X and Baby Boomers to think AI adoption will lead to a decrease in jobs. “If you’re at the end of your career, you’ve gone through a lot,” says Trevor Hawkins, manager of employment agency ManpowerGroup’s Canada operations.

Gen X has worked through the Great Recession, the dot-com bubble, the beginning of the internet in offices, and the smartphone revolution. “You’ve seen a lot of highs in the economy, lows in the economy.

You’ve weathered the storm quite a bit right now, so you’re not going to be as pessimistic about it.” A 47-year old working in legal sales, who asked I not use her name to protect her job, says adopting AI late in her career took cognitive dissonance.

She has moral qualms about the technology’s environmental footprint, but also sees how it has made her more efficient.

That mindset shift came after her employer pushed employees to do more, and do it with AI. “You’re being forced to,” she says. “There’s no question.” For all its benefits, like spinning up a presentation quickly, she describes the process of learning to use AI at work as “exhausting,” and says she took this job because she wanted work-life balance to raise her kids.

She had that, until AI upped the ante.

Now, she’s trying to map out the final few years of her career (she plans to retire on the earlier side) by future-proofing herself, focusing on the people skillsets needed for presentations and training content. “Most people in corporate are just trying to make it to a point where they are fine financially,” she says. “You just don’t know when your ticket is punched.” Others, still working, are less enthusiastic and less worried about AI, but they’re biding their time and have no intention of learning new tricks.

James Seger, 54, who works in customer service, is eying retirement in the next five years.

He says his employer hasn’t pushed AI aggressively, but Seger still thinks the tech will lead to cut positions. “It might be a good idea for me to learn AI, but I’m not going to,” he says.

Seger’s identity isn’t tied to his work, and he’s saved well throughout his career.

Now, he hopes to hold on to his healthcare and save a little more, but adapting to a changing workforce isn’t on his mind. “If I won the lottery — you hear people say, ‘oh, I’ll still work.’ Those people are fools,” Seger says. “I would be gone.” Amanda Hoover is a senior correspondent at Business Insider covering the tech industry.

She writes about the biggest tech companies and trends.