A historian and a futurist walk into a bar. The futurist says, “Ten years from now, we’ll be served by AI bots who plan our drinks based on a new algorithm!” The historian replies, “I’ll take a shot of that 20-year-old scotch—at least I know how that story ends.”

Probably not the best joke I’ve ever written, but it captures a shared dilemma: we stand perpetually between a past we think we understand and a future we hope will be different. Yet here we are in 2025, watching economic instability, political upheaval, and social fracturing unfold in patterns that echo 1929 with disturbing precision. The question isn’t whether we’re repeating history—we clearly are. The question is why we can’t seem to learn from it.

The Pattern We Keep Missing

If you’ve been following economic news or scrolling through Substack posts, you’ve seen the comparisons: the 1929 Stock Market Crash that ended a presidency and launched Americans into the Great Depression. The parallels to our current moment are striking—market volatility, wealth concentration, political polarization, and a collective sense that something fundamental is breaking.

Yet unless you’re a student of history, these patterns remain invisible. The current chaos seems unprecedented, even spooky. But for those who know the past, the future—however uncomfortable—feels grimly familiar. We’ve been here before. We know how this story ends.

Why We’re Condemned to Repeat

As both an arm-chair historian and a trained psychologist, I believe we are indeed condemned to repeat our past, and for good reason. Some of us replay history unconsciously, absorbing and reenacting the patterns learned in our family of origin. Others cling consciously to old ways and traditions, hoping they’ll provide protection and guidance in these fraught times.

But there’s a deeper psychological truth at work: humans prefer fiction to raw, uncomfortable reality. We default to fantasy, dreaming, denial, and fabrication because these offer temporary release from what’s increasingly painful to face.

We’re seduced by promises of something better—better homes, better education, bigger bank accounts, better bodies, better everything.

People in authority understand this vulnerability and exploit it. “A chicken in every pot and a car in every garage!” Republicans promised that in 1929. Today’s promises involve cryptocurrency and other glittering distractions. Different decade, same playbook.

What Happened Then—And What We Refuse to Remember

The Crash came in October 1929. It didn’t end with a market correction or economic reform. It ended over ten years later with a World War that killed an estimated 40 to 60 million people, military and civilian combined.

After World War II, the United States saw its role in the world expand dramatically. There seemed to be no barriers for every (white) American to have a good-paying job, a house, a car, quality education for the kids, and of course, a color TV. But this prosperity had a cost that’s conveniently forgotten in our nostalgia: it was built on exclusion, exploitation, and a global order maintained through threat of nuclear war.

The New Weapon Against Memory

Here’s what makes our current repetition more dangerous: Artificial Intelligence is distorting what we collectively accept as “fact” with frightening speed. Too many of us are ill-equipped to separate the artificial from the intelligent. Truth and fiction have become increasingly interchangeable, making it even harder to recognize the patterns of history.

In the wrong hands, AI isn’t just a technological tool—it’s becoming the mechanism through which we rewrite and forget our past. When truth itself becomes malleable, when algorithms curate our reality and shape what we see, the lessons of history become easier to ignore, deny, or simply never encounter.

Asking ChatGPT

I asked ChatGPT what George Orwell—who wrote 1984 in the late 1940s—might write about our current moment:

If George Orwell were writing today, he would likely warn of a world where surveillance is seductive rather than forced—where we willingly trade privacy for convenience and truth is drowned in an ocean of algorithmic noise. The new Ministry of Truth would operate through search engines and content platforms that shape what we see, not by censorship but by curation. Attention itself would be the battleground, with distraction eroding our ability to think critically or rebel. Predictive AI would act as a modern Thought Police, subtly steering behavior under the guise of safety. Yet, Orwell would still hold out hope—that genuine human connection, quiet reflection, and acts of truth-telling remain our last defenses against control.

What do you think?

The Variable Called Choice

Historians have the advantage of knowing how things turned out. They can trace the pathways that led from prosperity to collapse, from democracy to authoritarianism, from peace to war. Still, those pathways can be wrong. As Winston Churchill noted, “History is written by the victors,” which means we must be skeptical even of the lessons we think we’ve learned.

Choice is the unknown variable. We can choose to gather our wits and resources and stop the freefall into economic chaos that’s no longer on the horizon but directly in front of us. We can choose, individually and collectively, to curb our greed and learn to protect and preserve resources rather than consume without conscience. We can choose to open our hearts and minds to the necessity of caring for one another.

Perhaps the most likely outcome, given centuries of evidence—is that we will choose to continue doing what we’ve always done: take steps toward an idealistic society, then sabotage our progress, regroup, and start over again.

Why Can’t We Learn?

The uncomfortable answer is that learning from history requires something most of us lack: the willingness to sit with discomfort. It requires acknowledging that our prosperity may rest on others’ suffering, that our certainties may be illusions, that our leaders may be lying, and that the systems we trust may be fundamentally broken.

It’s psychologically easier to believe “this time is different” than to accept we’re simply actors in a very old play. It’s easier to chase promises of cryptocurrency riches than to remember what happened when everyone believed the stock market would rise forever. It’s easier to let algorithms tell us what to think than to do the hard work of critical thinking.

We Have to Change

We can’t learn from history because learning would require us to change—not just our policies or leaders, but ourselves. And that kind of transformation demands more of us than most of us can muster while we’re still comfortable enough to avoid it.

The question for our generation isn’t whether we’re repeating history. We are. The question is whether we’ll recognize the pattern in time to write a different ending, or whether historians a century from now will look back at us and wonder, as we wonder about 1929: how could they not have seen it coming?