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064: The Lost Art of Speaking to Strangers

🖼 Social Anxiety + 👉 Techniques for Talking to Strangers

Jason Shen
Jason Shen
4 min read
064: The Lost Art of Speaking to Strangers

This is the 64th edition of Cultivating Resilience, a weekly newsletter how we build, adapt, and lead in times of change—brought to you by Jason Shen, a 1st gen immigrant, retired gymnast, and 3x startup founder turned Facebook PM.

This past week was difficult. I wasn’t sleeping well, work was very demanding, and I was behind on a number of personal tasks. I noticed myself catastrophizing a bit—thinking that everything is bad and will continue to be bad and I need to take some dramatic action to change up my situation.

But then I had a chance to step back and see that it was more a bunch of disconnected things that all happened to land in the same period. And while that didn’t change my situation, it helped me feel better about what it all “meant”. Which is half the battle sometimes.

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🧠 The power of chatting up a stranger

A few issues ago I wrote about ways of adding a little disorder and unpredictability to your life. Talking to strangers is a great way to do that and I recently came across some writing and some real-life reminders of this truth.

The words come from a article in the Economist that reviews three books that explore talking with strangers. These books have been published in a time where we have assiduously avoided human contact and probably interacted with fewer strangers than at any other point in our lives. Which is to say, we are all kinda unpracticed in speaking with strangers.

First, interacting meaningfully with a new person can bring huge rewards—but it is a skill that must be cultivated and can easily be lost. Second, the self-segregation of modern Western societies means that, for many people, conversing with some fellow citizens seems pointless, undesirable or outlandish. The second problem exacerbates the first: if you consider others beyond the pale, why make the effort to get to know them?

A few weeks ago I went out to dinner on my own, without my phone. That alone turned my trip into a bit of an adventure. I needed to ask for directions at least once to get to my destination, a Mexican-Korean fast casual place. As I waited for my order to come through, I saw another single diner come through. We both ate in silence and he seemed mostly buried his phone.

After a while, I made my opening bid - asking him how his bulgogi burrito was. We started a conversation and I got to hear about his life as a professor of anthropology who spent the past 2 years in Pakistan, teaching remotely as COVID raged through the US and his home country. Had I brought my own phone, we surely would not have had such an encounter.

In mid-life and beyond people can still experience the joy of a random meeting, however short, which somehow touches a nerve. That might involve nothing more than a smile, or a chance remark that hits an emotional spot; or it might be an unexpectedly deep conversation on a plane or train, a surge of mutual understanding that is life-affirming even if the interlocutor is never seen again.

A friend of mine was delayed on a flight and ended up chatting up one of the other bummed out passengers. They hit it off, as sometimes happens when you’re bored and open to company. Well my friend discovered this passenger happened to heading to the same post-layover final destination, New York City, and in fact lived in the same neighborhood. They exchange numbers, text a bit on the first leg of the flight, find themselves seated in the same row on the second leg, and share a cab home.

Long story short and this will perhaps upset (or inspire) some of my single readers, this friend, who has been seeking a longterm committed relationship since before pandemic, has finally found one. And she met this lovely man as a total stranger at an airport. And that’s gotta give you a bit of hope in these strange times.

As lockdowns lift, people are now stumbling back into a world of accidental collisions, some eagerly, some queasily, most with an odd sensation of novelty after a year of hibernation. The lesson of these books is that the easing of restrictions is not just a coveted opportunity to reconnect with those you love and resemble. It also restores a freedom, long taken for granted even if little used, to come to know the profoundly different.

The Vital Art of Talking to Strangers (economist.com)

Why We Should Talk to Strangers More (theatlantic.com)

🖼 Social Anxiety

Making friends when you’re older is way harder. I give props to anyone who can keep it up past 40.


👉 Techniques for Talking to Strangers

I found this informative yet hilarious video that’s part interview and part “journalist tries expert’s advice” on talking to strangers. It flirts the line between earnest and satire and I’m not sure what to make of it. But I can promise you’ll either learn something, or laugh while watching it. Hopefully both.

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Jason Shen

Human(e) technologist on a mission to help build resilient teams and organizations. Former NCAA gymnast and three-time startup founder.