What a Roundtable on the American Dream Tells Us About Success Today

On Wednesday, I attended a national roundtable on the American Dream organized by AllSides and Newsweek. The discussion centered around how people today define success and opportunity, and what it takes to fulfill personal aspirations. A retired health care professional expressed worry that the American Dream would be harder for his children and grandchildren to attain.

Different viewpoints emerged regarding the prospects for his two children. Others highlighted factors such as housing costs, expensive education, and a technology-driven job market as potential barriers to achieving the same level of security they had envisioned for themselves. One parent expressed concern that if they did not provide for their daughter, she would lack a financial future altogether.

The traditional markers of the American Dream—homeownership, a steady job, and a secure retirement—remained significant in our conversation. However, it was uncertain whether the next generation could reliably achieve these milestones following the same path as previous generations. Newsweek's Editor-in-Chief Jennifer H. Cunningham and AllSides Co-Founder and CEO John Gable introduced the event, emphasizing that while each individual's version of the American Dream differed, it was a shared aspiration.

Participants were deliberately selected to represent diverse ages, locations, political leanings, and life experiences, and they were empowered to guide the conversation independently. Prompts on the screen encouraged attendees to listen, seek common ground, and share personal experiences. Many participants still conceptualized success through indicators similar to those of their parents, such as spending 30 or 40 years with the same employer, earning a pension, owning a home, and eventually providing financial security to family members.

A retired health care manager had accomplished some of these benchmarks but was less optimistic about younger generations. "I've managed to own a home and secure a reasonable retirement, but my children are not in the same position," he remarked. Another group member owned her home and possessed a pension. After 33 years of service at two institutions, she had gained the flexibility to allocate more time to volunteer activities and pursuits of her choosing, considering this aspect of achieving the American Dream.

One woman pursuing a doctorate distinguished between the traditional financial dream and her personal objective of self-actualization. When it was her turn, I found the conventional checklist of familiar milestones less informative than the concept of having sufficient stability to determine how to live. Several of us had received limited practical guidance on financial matters within our households.

The son of an engineer recalled receiving minimal education beyond the importance of not overspending. Another participant grew up with the pervasive belief that money was scarce. Another participant traced a significant lesson from playing Monopoly with her father, who encouraged her to accumulate properties. Among the six of us, families passed down resources and advice to varying degrees.

Inheritances and assistance from relatives were mentioned alongside accounts of individuals who worked diligently for years without sufficient financial cushion. One woman described ending up in a markedly different financial situation compared to a sibling, despite shared upbringing, attributing the disparity to differences in education and financial guidance.

As we compared our circumstances with those of our parents, a recurring theme emerged: we were engaged in a different game. The comparison did not yield a straightforward conclusion. One person might have a more stable career or greater retirement savings while facing challenges in affording housing. Pensions served as a variable advantage, with one group member acknowledging theirs as rare today.

Family assistance could also play a role in achievements that appeared entirely individual from the outside. A 2026 report from Nationwide found comparable concerns in a nationwide sample. The "Financial Growth & Protection Index," based on a nationally representative online survey of 2,000 U.S. consumers aged 22 and older, revealed that 84 percent of respondents perceived the American Dream as primarily about financial stability rather than wealth accumulation.

Similarly, 84 percent believed that attaining financial progress was more challenging than it had been for previous generations. Fifty-three percent maintained that the American Dream remained feasible for individuals like themselves. A story illustrated how swiftly that security could be jeopardized. A group member who had been married for 37 years experienced divorce within the past six months.

Much of his planning had centered on a comfortable retirement with his spouse, and he had reached a point where they could contemplate ceasing work. Now, he was no longer residing in his home and was staying with a friend while navigating his next steps. Later in the discussion, we delved into risk beyond investment decisions. Job loss, unforeseen expenses, family obligations, and significant life events capable of disrupting years of preparation were also discussed.

The health care manager noted a generational distinction, suggesting that younger individuals faced more involuntary risks.