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Uncategorized • September 1st, 2026

A National Discussion About the "American Dream" Comes Down to... Money

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This post was written by Martha Engber and originally posted on her Substack, Vigilant Positivity. 

Last year I attended a national zoom call organized by Newsweek and AllSides, a nonpartisan news outlet, that talked about political violence following the murder of Charlie Kirk.

I recently attended another such conversation on “The American Dream.” The process was simple enough. You go to the AllSides Roundtables page to learn about upcoming topics. You sign up for a time and day that work for you from a list that provides a wide variety. Once signed up, you get a meeting link and join when the time comes.

Upon entering the meeting, you watch a prerecorded message from Jennifer H. Cunningham, editor-in-chief of Newsweek, and John Gable, co-founder and CEO of AllSides. Then you’re randomly paired with the other Americans who signed up. You’re given a question to discuss for an allotted period of time. Your group can take more or less time to answer, after which you move to the next question.

I had four other people in my group and within only a few minutes, I made a startling realization. I’d always thought of “The American Dream” in terms of various achievements and the acquisition of certain items: a spouse, kids, a good job, a house, a dog. But you start talking to other people, what the topic boils down to is financial stability.

The insight effectively boiled away my lifelong perception of The American Dream, complete with inspirational images of happy Americans and corny taglines about “freedom” and “ambition,” to the bare bones concept of whether Americans feel they’ve got the money to enjoy the freedom and ambition to, say, buy a home or start a business. More importantly, have they got the skills and knowledge to properly handle the money they earn.

I’ve always been aware of the growing problem of income inequality and the wealth gap. I’ve been hesitant to post about these very hefty topics because there are so many books written by experts. But I plan to do so more often, but in smaller increments that are more digestible for all of us.

Because the one thing economists and political scientists agree on is that a widening wealth gap works against democracy. To participate, citizens need to feel they have the time to take part, rather than worrying about how to survive. And the richer some people grow, the more influence they can exert on government to exact changes that may not be beneficial to Americans, or the world.

Here’s what I heard from my fellow Americans, three of whom are currently involved in Common Ground Movement/bridging organizations like Braver Angels.

NOTE: I changed all names to maintain people’s privacy.

Is the dream still achievable?

The consensus was a qualified no, or at least, not the way it used to be. Ken, who grew up in the San Francisco Bay Area and now lives in Palo Alto, remembers when home prices there were actually affordable. What he’s watched since is a transfer of wealth to a small percentage of people. While he considers himself lucky to be living the dream himself — “I know what America is based on works.” — he told the group that the wealth transfer has left a lot of people out in the cold.

Tina, who grew up in foster care in Washington, felt that gap most acutely. Coming from poverty and managing ongoing mental health struggles, she’s found it harder and harder to buy a home, which she pointed out is exactly the thing that jumps the divide between the wealthy and poor. Yet she’s trying to remain positive and has been applying to grad school .

Hank, in D.C., was refreshingly honest about why he owns a home and has tenants at all: luck, privilege and a small inheritance. Not hard work alone. Alan, out in West Los Angeles, is proof the dream can be achieved and then lost. He built one successful company early in life, started another that failed, and is now 74 with no money. He’s still here, still moving, primarily because his wife had a successful career and now has a good pension.

Between the four of them, the dream looked less like a ladder anyone could climb and more like a set of circumstances — some earned, some inherited, some just lucky — that had to line up.

Do good financial habits matter, or is it mostly circumstance?

Everyone agreed habits matter enormously, but they also agreed habits are taught, or not, largely by accident of family and childhood. Alan’s grandmother gave him a coin each day, and explained what he’d done to earn the money, then took him to the store the next day to spend it. Hank’s parents watched a financial program together when he was young, and it stuck enough that he learned how to write checks before most kids his age. Ken had jobs his entire life starting young, including construction work when he was sixteen, and his parents taught him about debt and credit cards directly, on top of running their own real estate investments. Lila started working at 14, primarily because her teacher parents were only paid for the months they worked, which left the summers hard to navigate. She had an aunt who taught her about investing. In short, her upbringing made her deliberately want less, so she could feel more financially secure.

Tina’s story was the clearest counterpoint. Housing and safety were the priorities growing up in foster care, so credit, budgeting, and the rest simply never got taught. She took on significant debt for college because she was surviving, not planning. Now, with recent policy changes making it harder to return to school, she’s stuck after getting into a much better graduate program, yet the harder, unfunded path is the only one that seems open to her.

“It comes down to money,” she said. “It’s stressful and affects your physical and mental health.”

Her financial education has been self-taught in adulthood.

The through-line for the group was that the people who learned good habits early almost universally learned them from a parent, grandparent, or aunt who took the time, and the people who didn’t, paid for it later, regardless of how hard they worked.

Is risk-taking necessary?

Here the group split more by temperament than circumstance. Alan called himself a risk-taker outright. He experienced a big early success at the age of 26, which got him hooked, and he’s taken plenty of risks since that haven’t paid off. Ken said he was only able to take the big risks he has because he chose not to marry or have kids. Hank’s small inheritance is what let him quit his job and start his own organization a few years ago; risk enabled by a cushion, not only courage, though I’m sure it took a lot of the latter.

Lila offered the clearest dissent: she’s not convinced risk is the answer at all. Her own approach leaned more on making better choices. She doesn’t think everyone needs to go to college and take on major debt to get somewhere. She says creativity is important, as is the ability to hang in there. She took risks through her 40s but is in saving mode now.

When the group was later asked directly whether the only people who truly reach the dream are those willing to risk it all, Alan said he used to agree with that statement, until he lost everything. Ken pushed back hardest, noting that 60% of the country lives paycheck to paycheck, with no real risk capital to speak of, while a handful of billionaires — who do have that capital — hold ideas about how the country should run, yet Americans never voted for either those people or their ideas.

What hope is there for the next generation?

This was the most divided, and most sobering, part of the conversation. Alan, who works directly with young people, said they seem hopeless in a way his own generation never did. His generation protested and could see the impact of it, whereas he’s not sure today’s kids even believe AI is something they can take advantage of, rather than something happening to them.

Tina agreed the next generation is worse off, with the rich getting richer and the poor poorer, and added what older generations don’t fully grapple with: they didn’t grow up carrying the mental health toll of social media the way young people now do, which she thinks makes the younger generation more fearful and risk-averse.

Ken, who’s worked with students since the late 1980s, admitted he has no real frame of reference for growing up with an addictive device in your pocket. He raised something the rest of the group sat with: a handful of ideological theories, accelerationism, held by a small number of extremely wealthy tech figures who believe they’re the saviors of the planet. He wants a fair wage taken seriously as a baseline, and pointed out that just five people now hold a combined $1.2 trillion.

Lila was the group’s cautious optimist, betting that with AI “all bets are off.” But she has hope that young people will find their footing and end up better off. Hank offered the most measured note of the day, and maybe the truest one: what’s happened in the past is no guarantee of what happens next, for better or worse.

Conclusion

While we didn’t solve world peace, we did enjoy learning about one another’s experiences, which is why I highly recommend them. The system NewsWeek/AllSides developed gives all an easy, civil path to talking with one another.

If you’re asking what good such discussions do, I’d say they’re imperative for good mental health. We’re living through very divisive times, so learning to choose the positive over the negative — talking to people and feeling less alone rather than re-posting a nasty comment or article — goes a long way toward relieving stress and offering options for action.

The other great feature is that before you sign up for an AllSides Roundtable, you have to fill out a form regarding your various opinions on the topic. When you’re done with the discussion, you fill out the same form again, this time to see what part of your thoughts might have changed as a result of talking to others. AllSides then collates the responses into reports, which you can read here.

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