Informed Naïvety: The New Yorker's Game of Evolution
What a 100-year-old magazine teaches us about authentic transformation
In strategy, often the wrong question is being asked. The real question isn't "How do we adopt this trend?" but rather "How do we make this trend distinctly ours?"
A few weeks ago, I wrote about that universal "Spotify moment" - discovering an artist with millions of streams and wondering "How did I miss this?" It perfectly captured how something can be simultaneously massive and niche in our metamodern era. That same pattern is playing out in organizational transformation, where the goal isn't to find a singular "right" approach, but to navigate multiple coexisting realities with confidence.
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The New Yorker just provided a masterclass in this navigation with their new game "Laugh Lines." While they're no strangers to digital games - their crossword puzzles have been a staple of their online presence - this venture feels distinctly different. Instead of following the familiar path of word puzzles that many publishers have taken, they've created something uniquely their own - a game that transforms their legendary cartoon archive into an interactive experience. Even more fascinating is how they've introduced it: through a promotional video featuring Jesse Eisenberg, an actor known for portraying complex, introverted characters (most notably Mark Zuckerberg) with self-deprecating wit. The choice is brilliant - who better to represent the tension between intellectual tradition and digital evolution than someone who embodied the founder of Facebook while maintaining his reputation for thoughtful, slightly neurotic authenticity?
The game itself is quintessentially New Yorker: players sort the magazine's iconic cartoons chronologically, turning their archived cultural commentary into a game mechanic. It's an exercise in both historical appreciation and playful engagement.
What we're witnessing here is informed naïvety in action - that beautiful state where deep self-knowledge meets bold experimentation. The New Yorker knows they're late to the game(s), quite literally. They've watched other publishers like The New York Times build successful gaming verticals. They understand the trend toward gamification for subscriber retention. But hey, as The New Yorker approaches its 100th birthday this year, they're proving that if you start exercising early, you can stay fresh and vital well into your late age - even if some of those exercises are new to your routine.
But instead of letting this knowledge paralyze them or push them toward imitation, they've embraced their position as newcomers while leveraging their unique strengths. They're saying, in essence, "We may be new to games, but we know exactly who we are." Just as with that Spotify artist who's both undiscovered and massive, The New Yorker is simultaneously a latecomer to gaming and a pioneer in brand-authentic gaming experiences.
This leads us to three crucial insights about evolution in our current moment:
Strong self-knowledge enables authentic experimentation. The New Yorker didn't just make a game; they made a distinctly New Yorker game. They transformed their archived cartoons - a unique cultural asset - into gameplay mechanics. This isn't about blindly following trends; it's about understanding your core identity well enough to play with new forms.
Innovation should extend identity, not replace it. They didn't try to become a gaming company. Instead, they created a game that makes sense within their existing narrative. The mechanics require the same cultural literacy their readers already possess and value. It's an extension of their identity, not a departure from it.
Authenticity emerges at the intersection of tradition and transformation. By maintaining their sophisticated voice while adopting contemporary formats, they've demonstrated how organizations can evolve without losing their essence. The game feels both perfectly New Yorker and perfectly current.
This is what informed naïvety looks like in practice: stepping into new territory while staying true to your core. It's about acknowledging that you might not have all the answers about gaming or digital engagement, but you do know who you are and what you stand for.
In an age where organizations often chase trends at the expense of identity, The New Yorker shows us a different path. They remind us that successful evolution isn't about becoming something else - it's about becoming more distinctly yourself through new forms of expression.
And sometimes, that means turning your archived cartoons into a timeline puzzle game. Because why not? After all, informed naïvety tells us that not knowing everything shouldn't stop us from doing something - especially if that something is authentically, unmistakably us.
What examples have you seen of organizations successfully transforming trends through their unique lens? I'd love to hear your thoughts in the comments.
My city is at a crossroads: how to be sustainable - how to have a future - without losing sight of very old and cherished unique heritage and values? How can we, as you say, be our authentic place and people in a future that promises to shake the foundations of this culture and its expressions?
Evolution is often seen as abandonment of past ways and worldviews. Indeed, we marvel at strong changes even in our lifetimes. We don't easily recognize the throughlines - these evolutionary changes seem like overhauls or weird blips in the continuum. And so we eschew facing and grappling with the forces of possible futures. The challenge here is to address incrementalism vs. transformation with voices accustomed more to fixing pain points and either/or thinking than to experimentation. Experiments feel like strategies and are experienced as a loss of time and resources.
We know that certainty about forces and implications is impossible. Deliberate change raises the question of who gets to participate and decide, with the threat of hegemonic control. But dismissing any agency and letting "fate" take over seems like no one has control, and to many that feels more comforting.