Eleanor Mills recently argued that Gen X may prove to be the unexpected winners in the AI revolution. As the workplace shifts under technological disruption, she highlights how midlifers’ blend of experience and adaptability could become their greatest asset. But her framing also raises a bigger question: how do the different generations currently in midlife or later life – Boomers, Gen X, and the often-overlooked Generation Jones – each approach work, retirement, and the possibilities of later life?
Baby Boomers: Redefining Retirement, Again
Born roughly between 1946 and 1964, Boomers have been at the forefront of cultural and social change for decades. They were the first to question whether retirement really meant “stopping.” Many embraced second careers, volunteering, or portfolio lives long before “encore careers” became a buzzword.
Today, as the eldest Boomers move into their late seventies, financial inequality within the generation is stark. Some have generous final-salary pensions, while others, particularly women, have patchier work records and face real insecurity. What unites them is that they were the first to push back against the notion of retirement as a cliff edge. They showed us that later life could include reinvention, activism, and continued contribution.
Generation Jones: The Overlooked Bridge
Between the Boomers and Gen X sits Generation Jones – those born in the late 1950s and early 1960s. Too young to be true Boomers, too old to be Gen X, they grew up in the 1970s with different cultural reference points: the three-day week, punk, and Thatcherism. They were promised the optimism of the 60s but came of age in a more constrained economy.
Now in their 60s, Generation Jones faces a particular squeeze. They are often caring for elderly parents while still supporting adult children. They have had to adjust to later state pension ages, and many do not have the same level of financial security as older Boomers. Yet their adaptability – straddling both analogue and digital worlds – gives them a unique position. They often act as cultural translators: old enough to remember life without technology, young enough to embrace its benefits.
In later life, Generation Jones may not make as much noise as Boomers once did, but they are quietly shaping what it means to age with responsibility and pragmatism.
Generation X: The Pragmatic Survivors
Gen X (born between 1965 and 1980) often describe themselves as the “forgotten generation.” They came of age in a time of divorce, recession, and economic restructuring. Used to fending for themselves, many carry a streak of independence and pragmatism.
Now entering their 50s and early 60s, Gen Xers are at the heart of the AI conversation. They are young enough to have navigated the first digital revolution and old enough to bring decades of judgment and perspective. In Eleanor Mills’ words, they are well-placed to see AI as a “lifeline” rather than a threat.
For Gen X, later life may not look like retirement at all. With state pension ages rising, mortgages stretching further, and children boomeranging home, they may continue working into their late sixties and beyond. But unlike Boomers, many Gen Xers expect to combine paid work with side projects, freelancing, or purpose-driven ventures. Flexibility, not permanence, is their watchword.
A Shared Future, Different Pathways
Each generation brings its own strengths and pressures to the question of work, AI, and later life:
- Boomers showed us that retirement could be reimagined.
- Generation Jones are the bridge-builders, balancing care responsibilities with technological adaptability.
- Gen X are now stepping into leadership roles, combining pragmatism with digital fluency.
Rather than competing labels, these groups together form the backbone of the later-life workforce. AI may not divide us so much as it demands that all of us, whatever our birth cohort, remain open to learning, reinvention, and the possibility that later life still holds more chapters to write.
What strengths do you think your generation brings to work and later life?
