There is a scene in “The Devil Wears Prada 2” where legendary fashion editor Miranda Priestly, played by Meryl Streep, is walking alone through Milan’s fashion district.
Her influence has been built on instinct and staying ahead of the culture. But in an industry increasingly shaped by social media, younger voices and constant reinvention, she begins quietly questioning her own relevance.
Arriving back at the hotel, she asks her husband, Stuart, when a person knows it’s time to step aside.
“You’ll know when it’s time,” he says. “You’ll just know it.”
It’s one of the most common mantras about work, aging and ambition, and it assumes that people will instinctively recognize when to slow down, step away or reinvent themselves.
But despite Stuart’s attempt to reassure his wife, that moment is no longer clear in our graying society.
I research aging, mental health and life transitions. As people live longer, work can become more than a paycheck. It’s a source of identity, purpose, routine and social connection. As a result, the question is no longer simply when to stop working, but what it takes to remain happy, healthy and secure as you age.
The retirement script was once clearer
For much of the 20th century, retirement was imagined as a more predictable life transition.
Careers tended to follow more linear paths, and older adulthood was commonly associated with stepping away from professional life and entering a “third act,” with more time to focus on family, leisure, personal interests and life outside the demands of work.
This was often seen as a well-earned reward after decades of work, and it became more accessible to Americans after Congress passed the Social Security Act in 1935 and pension coverage expanded rapidly after World War II.
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But over the past several decades, demographic and economic changes have significantly altered how people experience work and aging.
For one, adults are remaining in the workforce longer.
In 1991, the average retirement age was 57 years old.
Now, according to the U.S. Bureau of Labor Statistics, adults age 65 and older remain one of the fastest-growing segments of the labor force, with nearly 1 in 5 holding jobs in 2024. The number of employed Americans in that age bracket rose more than 33% between 2015 and 2024.
Several factors are driving this shift. Life expectancy is the highest it’s ever been, and some adults continue working because they want to remain active and engaged. But others are staying on the job due to the rising cost of living, their employer-sponsored health insurance, caregiving responsibilities or low retirement savings.
Even as the U.S. economy increasingly depends on older adults remaining in the workforce, cultural attitudes about aging and ambition have not evolved at the same pace.
To stay active or to step away
Society sends increasingly contradictory messages about what aging is supposed to look like.
On the one hand, older adults are encouraged to remain active, productive, healthy and engaged well into their golden years. Concepts such as “successful aging” often emphasize continued workforce participation, independence, productivity and purpose.
Yet older adults who remain visible in leadership or influential professional roles have also found themselves increasingly criticized for failing to step aside.
Samuel Moyn’s May 2026 cover story in Harper’s Magazine, “The Old Guard,” argues that America has become a “gerontocracy,” in which older generations disproportionately dominate politics, wealth and institutions, leaving younger Americans politically alienated and economically blocked from advancement.
Moyn’s article highlights legitimate concerns about generational transition and opportunity. However, it also risks overlooking the growing number of older adults who are not working longer solely out of ambition or unwillingness to step aside, but due to financial realities, caregiving responsibilities and economic insecurity. A 2024 AARP survey found that about 1 in 4 U.S. adults over 50 say they expect to never retire.
What are you hanging up, exactly?
Then there’s the emotional meaning of work itself, particularly in a culture like the U.S., where identity and self-worth are closely tied to professional relevance and productivity. Work ultimately offers more than money and power.
Research in gerontology, rehabilitation and occupational psychology increasingly shows that work may also reinforce your sense of self, while providing structure, social interaction, routine and meaning, especially in later adulthood.
At the same time, many of the traditional spaces that once fostered social connection and belonging outside of work, such as civic organizations, bowling leagues, churches and community groups, have declined in recent decades, contributing to a more isolated and socially fragmented society.
In the U.S., loneliness and social disconnection are increasingly recognized as major public health concerns. Work can be one of the few places where people continue to feel visible, needed and socially anchored.
This isn’t an argument for working until the grave. For many people, retirement is often associated with improved mental well-being due to less stress and more opportunities for leisure and personal time.
For some adults, however, stepping away from work can elicit feelings of isolation or diminished purpose, particularly if their jobs were deeply connected to their identity and daily routines. Research on the transition into retirement suggests that social connection, health and financial stability all shape post-retirement well-being.
Perhaps the real challenge today is not that people refuse to step away from work. It is that modern life has made that moment of recognizing “when it’s time” far less clear.
