Become friends with serendipity

Become friends with serendipity

"Meeting someone by chance feels like pure magic. There’s a thrill to meeting someone special on an airplane or during a lunch break at a park. And business deals made on the golf course often seem to work out better."


“We met at a speed-dating event.” 

Have you ever heard anyone in a successful, long-term relationship say this? I haven’t. I

also can’t I remember the last time I heard about a great deal or connection being made at

a networking event, you know, the kind with nametags.

Kind of weird, right? These two types of events seem like they should work wonders

because everyone is “qualified,” meaning they’re available and looking. But there can be

something stiff and unnatural about networking. Maybe it’s a little too obvious that

everyone’s looking for someone who can help them get ahead. Also, both events actually

ignore a very important element in attraction: serendipity.

Meeting someone by chance feels like pure magic. There’s a thrill to meeting someone special on an airplane or during a lunch break at a park. And business deals made on the golf course often seem to work out better.

Throwing a veil over the exchange can create a much more genuine connection. Think of

the cliché of people who join a country club and barely exercise. And (for those who do

want to exercise,) there are lots of dating Meetups with a fun layer like, “The Singles

Hiking Group”. It could just as easily be called “The Hiking Group”. The key is anything

can act as an excuse to start talking with someone new.

I would almost say that online dating or posting your resume online has a little more

serendipity than speed-dating or a networking event. At least you still have to find each

other, and there is some intrigue and uncertainty when you do finally meet.

A networking event, by the way, is not to be confused with a charity event, art opening,

gala, launch party, or cocktail party where great networking really can happen. I guess

having a label stuck to your shirt kind of kills any serendipity. “Hi there...um, Bob. So

what do you do?” Nooo! Run away!

Something we found at Jaunty is that serendipity is everywhere and a huge part of what we call “luck” is actually awareness and skill sets. Looking for people around you in any setting, can be like networking anywhere!

My last two long-term relationships were from meeting on the street and at a chill bar.

These both felt very spontaneous, especially the latter, since I wasn’t even looking for

relationship since I’d just gotten out of one. But that little hello turned into us talking for

hours that seemed to fly by. You can’t plan for that stranger to be there at the right time

so it feels pretty special.

My last trip to NYC was a great success due in part to a conversation I had with a

stranger, years ago at a NY bar. The woman has since become a wonderful friend and

when she heard I was frantically searching for a place in Manhattan, she set me up with a

family member’s apartment that was walking distance of the Jaunty office. You really

never know where a bold approach will take you.

Stop and think about your last serendipitous moment. If you’re struggling to think of

something, I’d suggest changing some social behaviors to help encourage them.


The way I see it, technically there are way more magical moments around you than

planned opportunities. Walking through downtown, getting a coffee in your local café or

grocery shopping, all have a surplus of spontaneous moments. On the other hand, there

are a limited number of singles or networking events in anyone’s calendar.


“But Eric,” you say, “At least I know that they’re looking.” Sure, if you meet someone at a speed-dating event you know they’re single and folks at a networking event want to talk business. (Though I would argue they might be there because their social circle may be a bit weak.)

Okay, so maybe you find out that the person you chatted up at the beach isn’t single or

doesn’t need your services. That’s cool. Maybe you can be friends and if you did a great

job in your interaction, then they might have a cute friend or the perfect business

connection which comes to mind down the road.

Here my social dynamos, is your friendly reminder: Be open to serendipity and

opportunities 24/7. Creating these opportunities takes practice, but as we found out at

Jaunty, it’s all-learnable. Plus, it’s always nice to have a good answer to, “How did you

guys meet?”

Written by Eric Waisman and edited by Fayette Fox


Eric Waisman

Founding Instructor
September 24, 2021

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