lessons learned talking to strangers in cafés

18 July 2019
18 Jul 2019
8 min read

And why the greatest teachers are often the least obvious ones

croissant and coffee

Stranger #1: “My top values are Freedom and Learning”

This was said to me by an energetic, completely unique and enthusiastic French man I sat next to at my favourite cafe (we both seemed to find the only outlet in the place). I’m not exactly sure how our conversation started. Probably the usual stuff; Where are you from, what do you do, etc. But in just minutes it felt like we’d been friends forever. He was so authentic. It was bizarre. Some people you really need to warm up — they take awhile to show the real them — but not him. He was an open book, instantly sharing his thoughts on life, his experiences and why he identifies with being European. His openness completely accelerated our friendship, and made me realize just how important it is to invite people in with your personality rather than shut them out if you want to make friends in a new place. We got along so well we ended up going to yoga together and meeting up again afterwards.

Invite people in with your personality rather than shut them out if you want to make friends in a new place.

Here are some of the amazing lessons he taught me in our brief, but rich conversation on life: On freedom and learning:

“Freedom and learning are my #1 values. If I don’t feel absolutely free where I am, I feel like I’m in jail. Us French people don’t like to follow rules, but we are respectful when we don’t follow them. If I come back late to my apartment, I’m quiet, I’m respectful. I am willing to follow rules if they’re smart and interesting, but if someone can’t explain to me why I need to do something, I don’t want to follow it.

And as for learning — well, if you’re not learning, what are you doing? What’s the point of being here if you’re not going to learn both purposefully and passively from your environment and the people around you — just like we’re doing right now.”

On independence:

“What’s important is to live life for yourself and to take initiative on your own. Don’t wait for people to pull you along for things — it is no fun that way. Be able to decide you want to do something and then just do it on your own. I don’t get when people won’t do something because they don’t want to do it alone.”

On confidence:

He didn’t say anything explicitly about confidence, but you could just tell he was buzzing with it — and not the obnoxious, over-confident type of confidence — he had just reached complete peace with himself. He didn’t seem to want to waste any mental energy on a lack of confidence. He seemed to think life was too precious to waste even a moment of it questioning your ability to do or be anything you felt drawn to or inspired by. His energy beamed with courage, confidence and a zest for life you don’t see all that often. The whole conversation was just one big reminder about the importance of confidence and how it can light up your life if you build it up.

Stranger #2: A little kindness can go a long way

When looking for new living accommodations in a time crunch, I pinged every person I’d met since arriving in Singapore to see if they knew anyone looking to rent an extra room. One of the strangers I met spent the better part of a day messaging his friends, colleagues and land-lord, all for the sake of trying to find me a new living set-up for the next few weeks. Through a number of third degree connections, he finally found something that worked perfectly with the timeline I was looking for, and essentially saved me from hostel-hopping around Singapore for a month. While to him the effort might have seemed small, just a few messages sent out and setting up some Whatsapp conversations, it made the world of difference to me for the rest of my summer.

The whole scenario just re-enforced a lesson that tends to fade away until it is flashing in your face because you’ve been affected by it: A little kindness goes a long way.

After this, we’ve shared a number of conversations and become better friends, with me constantly thinking of ways to pay it forward and spread the ripple of kindness he started where I can.

The lesson: Never under-estimate the impact of a small effort to help a friend, an acquaintance, or even a stranger.

Stranger #3: Take the time to explore when you have the freedom to.

One individual I met in my favourite café immediately introduced himself to me as I sat down at the same table as him. After talking for a few minutes, he told me that he had just moved here and was casually job searching, but mostly “city exploring”. City exploring? I was confused — I asked him what he meant. He replied with some insights which resonated deeply :

“It’s not often that you’ll move to a new place, and it isn’t a big career move. In my case, my wife had to move for work, so we came here pretty quick. I’m meeting with people here, searching casually for new work, but mostly I’m just enjoying exploring, taking photos of the city and being somewhere new without the pressure of immediately jumping into a new routined work-life.

I wake up, work out, go to a cafe, do some light work, maybe have a coffee chat, and then in the evening, I take my camera, and take pictures of all the beautiful parts of Singapore I’d miss if I was just working right away. It’s important to take the time to explore when you have the freedom to.”

I loved his take on this undefined move for him — he wasn’t in a rush to get to work, to fill every day with interviews and job-related meetings. He just wanted to experience this new place first, and then when he was ready or felt he needed to, he would find a job and begin the work routine which would fill the majority of his days and most of his time in this new place.

So often, we forget how unique it is to be somewhere for the first time.

Everything is new. The sights, the smells, the sounds, the people, the culture. Instead of rushing to get what we want out of that place — whether that be a new career, sandy beaches or the company of someone we’re visiting, we must remember to slow down and appreciate the opportunity to explore. No rushing, no pressure, no expectations, but instead to go into a place with only the desire to learn more about it, see more of it, and appreciate it from this new lens. In his opinion, taking pictures is the perfect way to do this — it’s an intimate way to get to know a new place.

The lesson: Fancy camera or not, taking the time to explore and see a place before rushing to do whatever you came there for is a practice worth thinking about when adventuring, travelling, moving or visiting.

Stranger #4: If someone interests you, talk to them.

One day while in a café, I was talking to someone about what I was studying, why I was in Singapore and where I’m from. After they left, the man sitting across from me asked me a question about why I was in Singapore and what I was hoping to get out of my experience. 45 minutes of talking later, I found out that he lead an investment fund which recently expanded into Asia. We had an amazing conversation about how generation gaps affect investing, what it’s been like for him to watch Singapore grow and evolve over the last couple decades and what we’ve both observed about the start-up culture here compared to North America and Australia. It was a wonderful conversation which lead to another coffee chat a few weeks later, catching up on both of our experiences over the past few weeks and him telling me more about what it’s been like to expand in Southeast Asia — he even brought along the leader of his APAC investing team to join us.

Ultimately, it was a truly wonderful, mutually beneficial conversation which lead to a connection which will likely remain strong even after I leave Singapore.

Some people have such strong, tight communities wherever they go in the world, and we always wonder:

How does that person know people everywhere?

What I learned from this interaction and many others is that people with great networks follow their curiosity when it comes to the people in front of them. The impact of following that curiosity right off the bat is that the person you might share a meaningful conversation with will likely remember you for life, and will be likely to connect with you again if your geography ever overlaps in the future. These rich and vast networks all start with the little decision to start a conversation. That little decision can take you anywhere, and can create relationships which last way beyond your trip.

The lesson: If someone is sitting in front of you and you feel the urge to talk to them, do it. It might be the only time you ever get to meet this person, but can lead to a world of value if you just start the conversation.

The real lesson in this article is that someone shouldn’t need to have a PhD or be a CEO for us to try and learn from them. When we embrace our environment and seek out new experience and conversations, it is truly unbelievable what we can learn from the people around us.


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