For May book club we tackled The Upswing, a sweeping look at the past 125 years of American history and an ambitious argument that societies move in cycles—from extreme individualism (“I”), to collective purpose (“We”), and back again.
The premise is simple: through decades of data on economics, politics, civic engagement, and culture, the authors argue that America experienced a dramatic upswing from the Gilded Age into the middle of the twentieth century. Wealth inequality declined. Civic organizations flourished. Political polarization eased. Americans became more likely to think in terms of shared responsibility than personal advancement. Beginning in the 1960s, however, those trends began reversing, leading us back toward a culture defined by individualism, inequality, and distrust.
What makes The Upswing memorable isn’t simply the historical analysis, it’s the conviction that because we’ve made this journey before, we can make it again. That optimism sparked a lively discussion in our group.
One observation that particularly resonated with the group was the authors’ analysis of language itself. They examined song lyrics over time and found a measurable shift from “we”-centered language to “I”-centered language beginning in the 1960s. It’s an elegant example of the book’s broader thesis: culture often changes gradually enough that we don’t notice it until someone graphs the trend.
That led naturally into a conversation about community.
One member described living on an island (literally) where neighbors naturally depend on one another more than many suburban communities do. Retirement for that member has become less about withdrawing and more about investing in relationships—hosting Thanksgiving dinners for friends, baking bread and pies, and delivering food to neighbors. The simple act of bringing someone a meal cuts through political differences. It reminds people that before we’re voters or consumers, we’re neighbors.
That point was particularly poignant to me: perhaps that’s what “we” looks like. Not grand national movements, but ordinary acts of care repeated enough times to become culture.
Another point shared from one of our members was from his MBA professor: after roughly two generations, societies tend to forget the lessons of major crises and repeat the same mistakes. That observation maps remarkably well onto the timeline presented in The Upswing. The people who lived through the Great Depression and World War II built institutions emphasizing cooperation, regulation, and broad-based prosperity. Their grandchildren inherited those institutions without inheriting the memories that created them. The result may be the pendulum swing the authors describe.
Several of us found ourselves wondering whether we’re living in what might someday be described as a “late-stage I” era. The phrase sounds ominous, but it captures something many of us feel: increasing concentration of wealth and power, declining trust in governments and institutions, and systems that seem designed to benefit those already holding influence. If that’s true, the obvious question becomes: how do ordinary people help start the next upswing?
One theme I kept returning to was how hopeful the book is compared to how I feel reading it today. The authors point to the corruption and inequality of the original Gilded Age as evidence that America has recovered from worse. Yet I found myself wondering whether our current moment is fundamentally different.
The corruption of the late 19th century was concentrated largely in monopolies, industrialists, and political machines. Today, those forces often feel intertwined with national political leadership itself. That distinction made it harder for me to fully embrace the book’s optimism.
Others shared a similar tension. One member described feeling nostalgic because he had lived through the height of the postwar “we” era. The book reminded him of the optimism and shared purpose of that period, yet it was difficult to imagine recreating it given today’s political climate.
Another member saw the book less as a prediction than as a recipe. Rather than promising that another upswing is inevitable, it outlines the ingredients that made one possible before: broader educational opportunity, more inclusive institutions, civic participation, and a willingness to prioritize long-term societal health over short-term individual gain.
Whether we choose to follow that recipe remains an open question. One perspective I especially appreciated challenged the idea that we’re living entirely in an age of “I.” The discussion connected the book to the concept of the Nash equilibrium: while individuals naturally pursue their own interests, societies often thrive when those interests become aligned with the common good. Perhaps the healthiest societies aren’t purely individualistic or purely collectivist, but continuously balancing both. That member also questioned whether we sometimes romanticize the 1950s and early 1960s. Were those decades really as unified as the data suggests? Or do we remember them selectively?
Even so, she appreciated that the book refused to be cynical. It argues that individual actions—bringing people together, building community, creating opportunities for connection—still matter. The pendulum isn’t moved only by the powerful or the wealthy.
No modern book club discussion would be complete without asking what artificial intelligence means in all of this. Would AI accelerate another “we” era by democratizing knowledge and creativity? Or would it deepen inequality by concentrating power even further among the companies that own the technology? Our group found itself split. Some saw enormous potential. Lower costs, broader access to expertise, and new creative tools could lift many people at once. Others worried that automation and robotics could dramatically reduce the number of people needed to produce economic value, further concentrating wealth and influence.
Several of us rejected the familiar answer that “it’s just a tool.” Tools reshape societies. The Internet was also “just a tool,” yet it fundamentally changed how we communicate, organize, and consume information, often in ways few anticipated.
One particularly interesting observation was that the tremendous prosperity of the 1950s and early 1960s may also have planted the seeds of the subsequent return to individualism. Success can breed complacency. If that’s true, perhaps today’s AI revolution will contain the seeds of both greater fragmentation and greater connection.
Another member reflected on something more personal: today’s AI systems often feel strangely affirming, eager to praise and validate us. While pleasant in the moment, that kind of interaction risks substituting simulated connection for genuine human relationships. If our need for authentic community is strong enough, perhaps that tension itself becomes part of the next upswing. We may eventually rediscover that technology cannot replace the richness of real people gathered around a table, sharing a meal, baking bread for a neighbor, or wrestling together with difficult ideas.
I finished The Upswing on my flight home from London and found myself torn between admiration and skepticism. I admired the historical scope, the careful use of data, and the authors’ belief that societies are capable of renewal. I wanted to believe their optimism.
But I also found myself looking for evidence that the conditions for another upswing already exist. The book points to civic organizations, reform-minded leaders, broad-based institutions, and growing social trust as early indicators of change. Those aren’t the signals I naturally see when I look at today’s headlines.
Perhaps that’s because we’re still in the middle of the story.
Or perhaps, as one member suggested, the book isn’t offering hope so much as a roadmap. It reminds us that the last upswing wasn’t inevitable. It happened because countless people chose, over decades, to build institutions, communities, and relationships that valued “we” over “I.” If that’s true, maybe the next upswing won’t begin with a sweeping political movement.
Maybe it starts by baking a pie for a neighbor.