The cruel optimism of thinking this time will be different

The conference room smelled like fresh markers and possibility. Through the floor-to-ceiling windows, afternoon light caught the dust motes spinning lazily above the mahogany table. Our department head stood at the whiteboard, uncapping a blue marker with flourish.

“This time,” he said, “we’re going to fundamentally transform how we operate.”

Around the table, my colleagues leaned forward with familiar hope. Even Ahmed, who’d survived more reorganizations than anyone, had that light in his eyes—that specific belief that maybe this would be the one that stuck. My hand moved across my notebook of its own accord, writing “KEY PRIORITIES” at the top of a clean page. The seventh clean page with those same words. That’s when I felt it: the peculiar sensation of knowing with absolute certainty that nothing would change while simultaneously believing that everything would.

We weren’t just repeating a cycle—we were performing a ritual as old as human consciousness itself, one that plays out in conference rooms and kitchens, in gyms and governments, wherever people gather to insist that this time will be different.

I started tracking this phenomenon three years ago, after that seventh restructuring meeting. What I discovered wasn’t corporate dysfunction but something more fundamental: we’re physiologically wired for what Lauren Berlant calls “cruel optimism”—remaining attached to ideals and conditions that actively prevent our flourishing. Not occasionally susceptible to it, not merely prone—actually wired for it, like our tendency to see faces in clouds or create meaning from randomness.

The fresh start effect shows we’re 62% more likely to pursue goals after temporal landmarks—New Year’s Day, birthdays, even Mondays. But what behavioral economists don’t emphasize is how this mechanism enables us to repeat failed patterns indefinitely, each time with renewed conviction that we’ve learned something essential from our previous attempts.

The scale of our collective delusion is staggering. 80% of New Year’s resolutions fail by February, yet we make them again each January with undiminished enthusiasm. More than 90% of dating app users have deleted and re-downloaded their apps, with 62% doing this multiple times, each return accompanied by genuine belief that they’ve finally figured out the algorithm of connection.

But this isn’t individual weakness manifesting at scale. It’s systemic design exploiting human nature.

Watch how it works in practice. Cities across America keep announcing “comprehensive solutions” to traffic congestion—always involving highway expansion, despite decades of evidence that more lanes induce more traffic. Los Angeles, Houston, Atlanta—they all follow the same playbook. The rhetoric in each announcement echoes previous failed expansions, yet planners present fresh models and citizens support new proposals, convinced that this time the engineering will work differently.

Or consider how we approach relationships. A friend recently told me about her breakthrough with her partner—they’d finally learned to communicate, really communicate, after years of the same circular arguments. She showed me the book they were reading, the communication framework they’d adopted. I didn’t mention that I’d heard this exact revelation from her eighteen months ago, complete with a different book and framework. The fight they’d “solved” was the same fight with new vocabulary, but her belief in transformation was absolute.

McKinsey reports that 70% of organizational change efforts fail—a statistic that hasn’t budged in 30 years despite revolutionary advances in technology, methodology, and understanding. The self-improvement industry generates $13.4 billion annually from this same human tendency, built almost entirely on repeat customers who genuinely believe each new purchase represents evolved understanding rather than repetition.

Productivity apps thrive on users who download them in bursts of aspirational energy, abandon them within weeks, then download competitors that promise to work with your brain instead of against it. Fitness centers structure their entire business model around this pattern—50% of new members quit within six months, 67% of memberships go completely unused, yet people return each January convinced that this time they’ve identified what went wrong.

These industries don’t just benefit from our cruel optimism—they actively cultivate it. They sell transformation while carefully maintaining the conditions that ensure we’ll need to buy it again. The cruelty isn’t in the hope itself but in how hope is harvested, packaged, and sold back to us in infinite variations.

But I wasn’t observing this phenomenon from some elevated vantage point. Three months into tracking everyone else’s cycles, I found myself at midnight researching productivity systems with the focused intensity of someone who’d never tried one before. My laptop history revealed the truth: Getting Things Done (abandoned after two months), Bullet Journaling (three weeks), time-blocking (one month), a hybrid system I’d created and promptly forgotten. Yet there I was, reading reviews of apps with AI integration and neuroscience backing, my cursor hovering over the download button with familiar anticipation.

The full weight of recognition hit like cold water. Every area of my life had these loops—the meditation practice that would revolutionize my mornings until it didn’t, the boundaries I’d set with crystalline clarity before they dissolved, the financial habits I’d establish with elaborate spreadsheets before returning to old patterns. Each attempt felt genuinely different, informed by previous failures, refined by experience. But the underlying cycle never changed.

What makes cruel optimism so insidious is that we never repeat exactly the same thing. We iterate, adjust, incorporate lessons learned. We approach the same problems with new language, refined strategies, marginal improvements. This isn’t Einstein’s definition of insanity—doing the same thing while expecting different results. This is doing essentially the same thing with cosmetic variations while believing we’re doing something fundamentally different.

Research shows it takes 66 days on average to form a new habit, yet most people quit by day 18. Every area of my life had these loops—the meditation practice that would revolutionize my mornings until it didn’t, the boundaries I’d set with crystalline clarity before they dissolved, the financial habits I’d establish with elaborate spreadsheets before returning to old patterns. Each attempt felt genuinely different, informed by previous failures, refined by experience.

The pandemic offered a mass experiment in this phenomenon. Remember the breathless articles about permanent transformation—how remote work would revolutionize corporate culture, how we’d learned to slow down, to prioritize what mattered? Watch any morning commute now. Check the return-to-office mandates. We didn’t just revert to old patterns; we returned to them with aggressive enthusiasm, as if to make up for lost time. The Great Resignation became the Great Return, and we acted surprised, though we shouldn’t have been.

Climate summits follow the same script with almost theatrical precision. World leaders gather to announce unprecedented commitments that echo previous unprecedented commitments. The targets set in Paris mirror those from Kyoto, which mirrored those from Rio. Each conference produces fresh rhetoric about historic opportunities and final chances, delivered by officials who seem genuinely unaware they’re reading from a decades-old script.

Even our most intimate spaces reflect these cycles. How many times have you decluttered your living space with the conviction that this time you’ll maintain the order? How many organizational systems have you implemented—for photos, passwords, important documents—each one accompanied by the certainty that you’ve finally found the sustainable solution? The cruelty lies not in our failure to maintain these systems but in our persistent belief that the next attempt will somehow transcend the structural reasons the previous ones failed.

I’ve started having different conversations about these cycles. When departments announce restructuring number eight, instead of asking “How will we make this work?” I ask, “What conditions would need to exist for this to work, and do those conditions exist?” Instead of creating implementation plans, we conducted what we called “autopsies of optimism”—examining failed transformations not to assign blame but to understand the mechanisms of repetition.

What we found was sobering but liberating. Every restructuring had failed for essentially the same reasons: misaligned incentives, competing priorities, and the gravitational pull of established patterns. But these factors were never addressed because addressing them would require changes that went beyond restructuring—changes to fundamental assumptions about how we operated, who benefited from current systems, and what we were actually trying to achieve. These patterns eventually led me to walk away from corporate life altogether, though the phenomenon itself extends far beyond office walls.

This points to the deepest cruelty of cruel optimism: it allows systems to remain unchanged by offering the perpetual promise of change. Every reset postpones the reckoning. Every fresh start delays confrontation with structural realities. We stay busy believing things will be different, which prevents us from asking why they remain the same.

Recognition offers its own form of freedom—not the abandonment of hope, which is just cruel optimism’s shadow, but something more complex. Call it clear seeing. It means approaching familiar patterns with different questions. Instead of “How can I make this work?” asking “What would need to be true for this to work?” Instead of “What’s different now?” asking “What remains the same, and why?” Instead of “How do I sustain motivation?” asking “What structures would make motivation irrelevant?”

These questions don’t sell memberships or apps or consultation packages. They don’t fill conference rooms with enthusiasm or social media with transformation stories. But they occasionally lead to actual change—the quiet, structural kind that doesn’t announce itself with fanfare because it doesn’t need to.

A former colleague recently asked me if I’d become cynical. I understood the question—refusing to participate in collective optimism can look like pessimism. But clear seeing isn’t about dismissing hope. It’s about distinguishing between hope that perpetuates patterns and hope that acknowledges them. It’s about recognizing when our optimism serves systems that profit from our cycles of resolution and failure.

There’s still something in me that regenerates—the part that wants to believe the next book, app, or system will be different. But now I recognize this feeling as information rather than instruction. It tells me I’m in the presence of a pattern that depends on my belief in fresh starts to avoid actual change. That recognition doesn’t eliminate the feeling, but it transforms my relationship to it.

These cycles persist everywhere I look. The language evolves—organizations are “transforming” instead of “restructuring,” becoming “agile” instead of “flexible”—but the choreography remains unchanged. The boulder waits at the bottom of the hill, and we approach it with fresh enthusiasm, genuinely believing we’ve discovered a better path up the mountain.

The cruelty isn’t in the hoping. It’s in systems that harvest our hope while ensuring we’ll need to hope again, in structures that promise transformation while maintaining the conditions that make transformation necessary, in our willingness to accept repackaged sameness as revolutionary change.

Until we’re willing to examine why we keep ending up at the bottom of the same hill—really examine it, with all its uncomfortable implications about who benefits from our cycles of optimism—we’ll keep pushing. And every time we approach the boulder, we’ll think we’re seeing it for the first time. That’s the cruel optimism of thinking this time will be different: it prevents us from asking why it never is.