The American Dream has long been tied to ideas of stability, opportunity and community, markers that Allsides roundtable participants said are becoming harder to measure.

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Adam Mills

By Adam Mills

AI Editor

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On Wednesday, I participated in a national roundtable on the American Dream hosted by AllSides in partnership with Newsweek, joining five other people in a small-group discussion. The conversation focused on how people define success and opportunity today, and what it takes to build the kind of life they want.

A retired health care manager worried that the American Dream would be harder for his children and grandchildren to achieve. One parent saw very different prospects for her two children. Others pointed to housing costs, expensive education and careers being reshaped by technology, all as potential impediments to achieving the same kind of security they had hoped for themselves.

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Speaking about her daughter, the parent said, “I really am concerned that if we don’t provide for her, she won’t have a financial future at all.”

The familiar markers of the American Dream—homeownership, a steady career and a secure retirement—still carried plenty of weight in our conversation. What seemed far less certain was whether the next generation could reliably reach them by the same route as those who came before them.

Before the discussion began, Newsweek’s Editor-in-Chief Jennifer H. Cunningham and AllSides Co-Founder and CEO John Gable opened the event with remarks about the purpose of the exercise.

“While everyone’s version of that dream is different, it’s something that we all share,” Cunningham said.

Participants were intentionally matched to bring together people of different ages, geographies, politics and life experiences, then left to guide the conversation themselves. Prompts on the screen asked us to listen, look for common ground and speak from experience.

Much of the group still described success through signifiers that would have sounded familiar to their parents.

One participant remembered an understanding of the American Dream that involved spending 30 or 40 years with the same company, collecting a pension, owning a home and eventually passing some of that security to family. The retired health care manager had reached many of those markers himself but was less confident about younger generations.

“I’m fortunate enough to have achieved home ownership and a reasonable retirement, but my kids are not in the same place,” he said.

Another member of the group owned her home and has a pension. After 33 years at two institutions, she said her financial position has given her the freedom to spend more time on volunteer work and other pursuits she cares about. She considered that freedom part of achieving the American Dream.

A woman pursuing a doctorate separated the traditional financial dream from her own goal of self-actualization. When my turn came, I also found the fixed checklist of familiar milestones less useful than the idea of having enough stability to decide how to live.

Those milestones alone said little about how people in the group had reached them. Several of us had received surprisingly little practical instruction about money at home. The son of an engineer remembered learning little beyond the importance of not spending too much. Another participant grew up with a persistent sense that money was scarce. A third traced one of her clearest lessons to playing Monopoly with her father, who encouraged her to accumulate property.

At least among the six of us, families passed down resources as unevenly as they passed down advice. Inheritances and help from relatives came up alongside stories of people who had worked for years with little cushion. One woman described ending up in a very different financial position from a sibling despite their shared upbringing, pointing to differences in education and financial guidance.

By the time we compared our lives with our parents’, a phrase had begun to recur: We were playing a different game. The comparison resisted a simple verdict. Someone could have a steadier career or stronger retirement savings while finding a home harder to afford. Pensions were another uneven advantage; one member of the group described hers as rare today. Family assistance could also sit behind achievements that looked entirely individual from the outside.

For many Americans, the American Dream is increasingly defined by financial stability rather than wealth and by whether the next generation can still get ahead.

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A 2026 report from Nationwide found similar concerns in a national sample. The “Financial Growth & Protection Index,” based on a nationally representative online survey of 2,000 U.S. consumers ages 22 and older, found that 84 percent of respondents see the American Dream as more about financial stability than building wealth.

The same percentage said getting ahead financially is harder than it was for previous generations. Fifty-three percent said the American Dream remains realistic for people like them.

One story showed how quickly that security could unravel.

After 37 years of marriage, a member of our group had gotten divorced within the past six months. Much of his planning had revolved around an eventual retirement with his wife, and he had reached a point where he believed they could stop working comfortably.

Now he no longer owned a home and was staying with a friend while figuring out what came next.

Later in the discussion, we began talking about risk in terms beyond investment choices. Job loss, unexpected expenses, family obligations and major life events capable of disrupting years of preparation also came up. The health care manager drew a generational distinction.

“I think there are more risks put on the younger generation now involuntarily,” he said.

The sharpest disagreement came over how far individual discipline can overcome limited income. One woman emphasized saving and careful trade-offs, recalling how her husband had taught her to weigh a purchase against the additional time it might require her to work. Another pushed back on the premise, pointing to people who make careful choices and still have little left over.

I saw merit in both arguments. Good decisions matter, but their impact partly depends on what remains after necessities are covered.

The earlier concerns about younger people became more concrete as the conversation continued. The health care manager worried about a grandson in computer art, noting that AI can also produce that kind of work and questioning what that could mean for employment. The parent who had spoken about her children believed one was likely to have strong prospects while worrying much more about the other.

College still represented opportunity to people in the group, but its cost and uncertainty around future careers made the familiar degree-to-job formula feel less dependable.

Late in the hour, several people noticed how much of a conversation about the American Dream had been consumed by money. Purpose and meaning had received far less attention.

The woman with a pension had already described money mainly as a tool that allowed her to spend time on volunteer work and other pursuits she cared about. The woman pursuing a doctorate separated financial achievement from self-actualization. Another participant described leaving a sales career she hated for change management, work she found more people-focused and meaningful.

The man rebuilding after his divorce was still trying to determine what came next. After 37 years of marriage, the retirement he had planned no longer looked the way he expected. His circumstances remained unresolved, but by the end of the conversation, he said he felt considerably lighter than when it began.

The hour did not produce a single definition of the American Dream. What emerged was a more practical measure of security: whether people still have choices when the plans they counted on no longer hold.

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