Thoughts on May ‘26 Freakonomics Podcast about The NYT and Games

I listened to the recent Freakonomics episode asking whether The New York Times has become a games company, and I kept thinking:

This is really a conversation about play.

More specifically, it is a conversation about the difference between games, play, and gamification. Those are not the same thing, even though we often treat them as interchangeable.

One of the guests described this as a potential “ludic century,” a more playful era shaped by games, interaction, curiosity, and participation. I agree with that idea, but I also think we need better language for the kinds of play experiences we are actually creating.

Because somewhere along the way, many organizations started confusing play with points systems, curiosity with competition, and engagement with retention metrics.

One of the most interesting moments in the episode was learning that The New York Times originally published articles AGAINST crossword puzzles before eventually publishing one in response to the aftermath of Pearl Harbor.

I think this shines a spotlight on the humanity of play.

In moments of uncertainty, stress, fear, or overwhelm, people often reach for pattern, curiosity, challenge, distraction, comfort, ritual, and meaning. We play. Not because we are avoiding seriousness, but because play helps humans process life.

That is part of why I have never fully agreed with the idea that true play can be fully contained by rules.

Games obviously have to have rules (by definition). But when the rules become the purpose, something important gets lost. The rules may structure the experience, but they are not the reason people return to it. Curiosity, experimentation, emotional experience, and intrinsic motivation are what make people stay engaged.

That distinction matters a lot when we start talking about gamification.

One of the guests criticized gamification and I nearly high-fived my phone. Most gamification extracts the measurable pieces of play while stripping away the human experience that made play meaningful in the first place. It often turns curiosity into compliance. (for more of my thoughts on gamification - feel free to take just five minutes to watch my DisruptHR Northern Colorado talk from 2025 titled Why Gamification Fails At Work)

That is why so many workplace “fun” initiatives feel exhausting instead of energizing. They become systems designed to drive participation and performance rather than experiences that foster exploration, connection, or intrinsic motivation.

The guest on the podcast made the analogy of reducing food and cuisine down to nutrition labels. Nutrients matter, but nobody gathers around a table because they are passionate about Vitamin B12. The meaning, ritual, emotion, creativity, and shared experience are part of what make food important in the first place.

Play works the same way.

The episode also discussed how The New York Times measures games by retention, which makes sense from a business perspective. What interested me more was why certain games retain people while others do not.

For me (reiterated by the guest and host), Connections is fascinating because even when it is difficult, it still feels satisfying. The challenge feels exploratory rather than punishing. Compare that to something like LinkedIn’s Pinpoint, which often feels stressful instead of engaging. I often roll my eyes at that game. It’s also got me wondering if timed games fundamentally alter the emotional experience because the pressure shifts the interaction away from curiosity and toward performance.

Which raises a fascinating question:
What if play is not a distraction from meaningful engagement, but one of the primary pathways into it?

I mean genuine ludic experiences rooted in curiosity, experimentation, agency, challenge, pattern recognition, and small moments of delight.

I think organizations that understand this distinction are going to build healthier and more sustainable cultures than the ones still trying to engineer motivation through badges, leaderboards, and artificial urgency.

Humans are not machines, and play is not just another productivity hack. Play is part of how we learn, connect, adapt, experiment, and make meaning.