The Pleasure of the Doing

Uncertainty and doubt create space for connection, but I fear we’ve given them up.

My friend Sarah used to declare “90s Rules” at parties. This meant that when we were trying to remember some pop culture fact, no one was allowed to look it up on the internet. If two people disagreed, we had to just argue it out. Factions would form, a victor or stalemate would be declared, and then, typically, we’d look up whatever we’d been arguing about as soon as we left the party.

Once upon a time, every conversation had been this way for us. Although we were all young in the age before the internet, we remembered that time well—most of us had graduated college before we had the internet on our phones. Our formative years were spent fighting about facts and collectively remembering details.

I thought of “90s Rules” recently, sitting with a group of leaders at my company, discussing the areas of content we might need to cover at our annual kick-off event. The second we needed to brainstorm, one of the execs suggested we ask ChatGPT for a list of possible topics. Another exec did, and they handed the computer generated list off to me. We didn’t have to work together. We didn’t have to argue about anything. We asked the computer, took its word for it, and moved on.

But we lose something when we operate this way too, because there is a pleasure in the doing: the way we learn about each other in collaborative conversations or the buzz of excitement you feel when someone else gives you a piece of the puzzle you didn’t have before that you can use to build. We can take pleasure in the debate about what year a movie came out or how old a celebrity was. We learn about our friends by hearing their rationales for whatever crazy statement causes us to call their bluff. If we play 90s Rules, it doesn’t matter if we’re right because no one can confirm who is right anyway.

Most of the companies I’ve worked for seem to be endlessly worried about people connecting on a human level. We spend hundreds of thousands of dollars on events and team-builders. We want people to be in the office, where they will theoretically collaborate well, simply because they are proximate to one another. But what collaborative work is there left to do, when the language-learning model has already given us its imperfect but efficient answer?

Connection and collaboration require doubt, uncertainty, conflict. They require that people move through messiness to clarity together. At times, it seems like we sacrificed our ability to connect with one another through collective problem-solving on the altar of efficiency, and now we’re trying to team-build our way back to a feeling that we could get for free if we just did work differently.

We could work together. We could argue. We could still ask the computer, but only so it could confirm what we already know: that humans are pretty smart when we put our heads together.