Where Are All The Interesting People?

What do you talk about when you’re with your friends? Work? Kids? Holidays? Investments? Gossip?

If you’re like me, 90% of your conversations are around banal topics like these. A couple of months back, I chatted with someone who bought a unit in the same new launch as I did. We had loads in common to talk about (the TOP date, the key collection process, what sort of renovation they were doing, etc), but I was bored out my mind. Surely we had better things to talk about than our inane administrative housing arrangements?

Perhaps, I wondered, it’s a class thing. Maybe rich people have more time and disposable income to engage with interesting ideas. But last night, my wife and I were having dinner at a restaurant when a bunch of Singapore Social-types walked in. They were well-dressed and articulate. We eavesdropped on their conversation (because why not), and they spent the entire night bragging and gossiping. One dude spent 20 minutes complained about what a shitty drive his Ferrari was. Another talked endlessly about his Michelin Star experiences in San Sebastian.

When did we become a boring, superficial nation of people, concerned only with the day-to-day and the occasional Instagrammable trip? By the way, this applies to me as much as anyone else: I too, spend way too much time talking about work, travelling or investing. My most common response to “How are you?” is the disappointingly mundane “so busy!”.

The ancient Greeks met in agoras to debate philosophy, discuss politics, hold debates, and instruct students. C.S. Lewis and JRR Tolkien met their friends twice a week in Oxford for “beer and wide ranging conversation”. They read from early drafts of their books or poems, while the other members responded with critiques or suggestions.

Why We’re Boring

Why has the quality of modern conversation fallen from these lofty heights? Let me brainstorm a few possible reasons.

We don’t have time to cultivate interesting ideas or experiences. We can barely find enough energy to manage the demands of work, taking care of the kids, running errands, and just keeping life going. There’s no time (or energy) to read books or talk to interesting people.

Our raw materials are terrible. Every chef knows that delicious meals always start with the best ingredients. Unfortunately, the media we consume degrades our ability to think and engage with good ideas: TikTok videos, gossip articles, social media, and Netflix (Singapore Social!) occupy the majority of our mindspace.

Peer pressure. Perhaps many of us do have interesting ideas and experiences to share, but we hold back on sharing them because we think that our friends won’t appreciate them. “Interestingness” doesn’t have to come from highbrow philosophy or culture. Perhaps we all have weird preferences or obsessions which we’re too embarrassed to share them we’re afraid of being judged.

We aren’t curious enough. Maybe our friends have a gold mind of ideas to share, but we fail to unlock them when we ask boring questions like “How’s work?” or “When are you travelling next?” Maybe we’re so focused on impressing our friends with our little lives that we fail to see how interesting they are.

We think we need to be experts. Sometimes we think that we need to be experts in a something in order to share about it. But some of my most interesting conversations have been when people asked questions to help themselves understand a topic better. Conversely, some of my most boring conversations have been when someone drones on about Web 3 or investments when the rest of the listeners have long checked out.

Is There Hope?

I believe that it is possible to have interesting conversations – we just have to find the right people and the right environments. I don’t mean those cheesy industry conferences where you have forced conversations with random people who just drone on about their lives.

For example, I meet Alvin and Jon from Dr Wealth for “beer and wide ranging conversations” once every few months. While we’re nowhere near the Inklings, our alcohol-fueled conversations have ranged from what aspects of life are driven by the Lindy Effect, why personal finance bloggers will never be as popular as lifestyle bloggers, and how mimesis explains US-China tensions.

I also occasionally get a chance to meet people who have chosen super interesting paths, like a friend who met her husband while walking a pilgrimage down the Camino de Santiago, to a friend’s husband who embarked on a multi-day race down the Amazon river, to Haresh and Terence at the Ministry of Funny who quit their jobs to start a comedy YouTube channel.

There’s something in our hearts that tells us that there’s got to be more to life than what our banal conversations reflect. It doesn’t have to be cool experiences or highbrow philosophy. But perhaps our hearts long for a purpose, a meaning, a quest for something beyond the day-to-day work, gossip and administrative humdrum of our lives.