Seeking Serendipity: An Introvert’s Guide to Making Serendipitous Encounters Happen
Serendipity. I first learnt this word in the beginning of my Sophomore year when I want to the PenApps hackathon, which for me was a wonderfully serendipitous experience. I had gone without a team and without any ideas or plans. But I’d remained open to people and opportunities around me, and ended up making new friends, creating a really cool web application and learnt a ton. I had written about my experience at the hackathon:
“I had been nervous and skeptical of going. But now I look forward to many more such experiences.
Step out of your comfort zone. Seek new adventures. Plan a spontaneous trip. Put yourself out there, and who knows, wonderful things may happen, without your planning them.”
David Perell has this to say on Serendipity:
“The best opportunities are the ones you never expected.
They’re serendipitous.
Serendipity is a state of mind. Serendipity births unexpected opportunities which fuel progress and push us in fruitful directions. By maximizing serendipity, you’ll accelerate your progress.
Serendipity is a skill, which means it can be learned.”
I reflected on some of the wonderful serendipitous encounters I have had recently and realized that aside from the whole chance element in these situations, there were a few things that I did which made them possible. Then I asked myself, what are these things that I can repeatedly do to increase my odds of having such amazing serendipitous encounters. So here it is - my guide for my future self and for you.
How Do You Increase Your Chances of Encountering Serendipity
Be Open, and Take an Interest in Other People
I was at a brunch cafe with my friend, David, in Brooklyn a few weeks back. We were talking about my interests in literature and theatre when he asked me a question about why I think Shakespeare is still relevant. This lady on the table next to ours overheard and chimed in, giving her perspective on the subject, which she seemed very interested in. We listened intently as she shared. Now, we could have left it there. I kind of wanted to - I had limited time with David and wanted to make the most of it, I didn’t want to be distracted by random ladies with European accents. But David being David, with his charm and his archetypal American ‘openness to the chances of life’ (as Henry James once put it), went on to involve her in the conversation. He asked about her life and work and what brought her to the city. We learnt that she had a very interesting job- something that combined criminology, psychology and reading people aimed towards helping the government with complex criminal cases and so on. And so, I got to learn about her fascinating work and life journey as she talked about her experiences doing theatre as a young girl in Europe to now working for the government, and how her learnings from the theatre world have proved valuable in her work around criminal behavior and psychology.
This exchange could have simply ended at her answer to the Shakespeare question. Thanks to David’s openness and active interest in her, it didn’t, and we got to learn about and exchange notes with this fascinating woman.
Of course, none of this is to say that you should pause and take an interest in people when you’re hastily grabbing your morning coffee on the way to work. There is a time and place for it. But being open and taking an interest in other people can certainly make your life richer and more interesting, if nothing else.
Use Visible Information to Strike up a Conversation
When we see someone for the first time, we don’t know much about them. But sometimes, there are things you can pick up on to strike up a conversation …
I was at a Starbucks one night in East Village and saw this guy reading the plays of Harold Pinter- which I had seen in college. I went up to him and simply remarked ‘that’s a fantastic playwright, I have seen a few of his plays’. That was all - simple, not overbearing. Worst case, he would have said something on the lines of ‘oh okay, cool’ and left. What really happened following that was a ten minute conversation that started with Pinter’s plays and moved on to theatre, literature and New York City. I learnt that he’s a director currently directing one of Pinter’s plays, I got to tell him that I’m a bit of an actor myself and he invited me to come audition for his next production.
Books… If you see someone reading a book that you have read, use that to start a conversation. “Okay, but I don’t go to cafes everyday”. Sure, how about some elevator conversations about people’s tattoos?
Yes, tattoos…. A few weeks back, I saw someone with a deathly hallows tattoo (if you know, you know) in the elevator of my office building and used that to strike up a conversation. Again, my conversation starter was incredibly simple and easy- something on the lines of ‘hey, I love your tattoo’. Now, it helped that tattoo was so specific that only true Harry Potter fans would get it. So we started talking about Harry Potter at first, and then we exchanged contacts- turned out that he was a Product Manager on the floor below mine. Are we good friends now? No. But maybe I can learn from him about the work that his team does in the company, maybe he can connect me to someone valuable, or at the very least another professional acquaintance I can talk to at the next social event in office. This works with clothing too- maybe someone’s wearing a t-shirt with your favorite comic book character.
The idea here is to find a shared interest based on any visual information that you may have.
Just Take The First Step
It was a Thursday evening and I reached my acting class in East Village at around ten minutes to eight, only to find out that the class had been cancelled that day. Somehow due to some miscommunication, I had missed the memo. Disappointed and flustered, I walked out the building. I started towards the subway station when I saw a poster for a play performing that night right next-door. It seemed quite interesting, and given that three hours of my evening had just freed up, I thought why not. I got into the theatre.
The show had just started a few minutes back, and there were still a few spots left in the audience. I bought my ticket and got in. It turned out to be absolutely incredible. Post the show, there was a reception with snacks and drinks. I took a glass of wine and wandered about.
The crowd was a mix of old and young, all well-dressed in their own regard- some in groups, few scattered about, few in a hurry to leave. I found my way over to a poster containing information about the playwright and the cast. A man about my height came and stood next to me, also studying the poster. I had no idea who he was and no specific reasons to talk to him or anyone here- I wasn’t here to ‘network’ or to make friends, and I’m usually the kind of person who likes to dash out the door from social settings where I don’t know anyone. But well, I was there and I always like to share perspectives after a piece of watching intimate theatre like this one. So I turned towards him and simply asked, ‘Do you know about the playwright?’. ‘Yes, I have heard of her,’ he replied. We then exchanged thoughts on the performance of the night, he brought about some nuances which I had missed. He then told me he knew the cast members, and even took me to meet them. I got to talk to them about their process while they were really interested to know my favorite bits of the show and my perceptions of specific scenes. It was wonderful chatting with them.
Following that, Will, the guy who had introduced me to the actors, and I went on talking. Turned out he is an actor himself, having trained at some of the best institutes in LA and London and is now in town for a production. We spoke at length about several things - art, acting, life as an artist in LA, London and San Francisco, making money as an artist and everything in between. He even invited me to his show happening in November.
It was a wonderful exchange and I learnt so much from just talking to him, not to mention getting to meet the actors of the performance, and getting invited to another show. None of this would have happened if I hadn’t said ‘Do you know about the playwright?’ to a random stranger I knew nothing about other than the fact that we had both just watched the same show.
As someone who used to be a painfully shy introvert (and perhaps still is to an extent), I am well accustomed with the feeling of wanting to run out the door when at some event where I don’t know anyone, like this show reception. My rationale for not going up talking to people would be - I don’t know what I would talk about with them. What if we have nothing in common? What if it’s just an awkward silence? These fears would always dissuade me from striking up conversations with strangers.
Well of course I wouldn’t know what I’d talk with a stranger! (Unless I’ve somehow researched them before and planned exactly what to talk about, but that’s not what I’m talking about here.)
But I took the first step, and the conversation just flowed from there. It will not always, but often it will. So take the first step. In the worst case, you won’t get a good response. You leave, they leave. End of story. But if it goes well, you have a wonderful conversation like I did, learn something from it, and who knows, maybe they invite you to their show ;)
Use Visible Information to find common interest and start a conversation. Tattoos, books, clothes are some of the obvious ones here.
Be Open, and Take an Interest in Other People - No shortcuts for this one, unfortunately. Taking a sincere interest in other people is the only way you’ll learn more about them and give them a chance to learn more about you. And yes, you don’t know where that connection will lead you, but that’s why it’s called ‘serendipity’ - a chance encounter’.
Just Take The First Step - Seriously, just go say hello. Or ask a question that seems relevant in the moment. Don’t worry about what you or they will say after that. The answer is maybe nothing, maybe a lot. But there is no downside to taking the first step, only upside.