In Search of Serendipity

I’ve noticed a curious thing recently, and it relates directly back to creativity and the ability to track trends, which is at the heart of marketing and entrepreneurship. I think of myself as a reasonably creative person and one that spots trends early, but I’ve realized that a lot of that ability stems from serendipity – chance encounters, discussions with strangers, exploring new places and just in general, being exposed to new things in unexpected ways. Juxtaposing ideas from one industry onto another. Being exposed to new ideas across unrelated fields, and seeing patterns emerge before others. Being challenged to view something in an unconventional way after a lively debate. Talking to new people – lots of new people. Or just plain being around artsy folk who seamlessly draw humour and double meanings out of a mash up of relevant cultural inferences in a piece of creative – that you just know is going the resonate at scale.

I’m missing some of that, and I think I can draw the parallel directly back to the absence of serendipity, or at least a significant reduction in it. Those chance encounters and resulting revelations, were largely generated in the past through travel, conferences, water cooler type discussions in offices, and social events. And right now, those are either on hold, or significantly reduced in nature. As much as I love online (and truly I do!) I’ve yet to generate the same type of serendipitous interaction that fuels my creativity and the trends radar.

I put this observation out to my Sunday morning newsletter subscriber base this past week, and was immediately inundated with replies observing similar feelings. It seems I’m not the only one searching for serendipity. But the curious things is, how successive the impact has been over time. Most people hadn’t been able to put their finger on a dramatic change, other than to observe they were sensing the same – something was missing. The loss of serendipitous moments has a cumulative creep impact. Over time the likelihood of creativity being adversely effected goes up.

Don’t get me wrong. I love this new online world we’re in. Just yesterday I met with a client in Brisbane, later had a meeting in San Diego, returned to Vancouver to meet with some faculty to discuss marketing, and then did a live workshop for an audience all across BC for 3 hours. Later in the evening, I did another presentation on behalf of a client in Melbourne for a group in Mumbai, India for 1.5 hours, which started at 9pm (9am the next for them). In between these activities, I did laundry, walked the dog, had a BBQ dinner with my family, and took a nap. I’ve been consulting online for years, but I can assure you this type of day did not exist prior to April 2020. It would have been filled with flights, airports, and a lot more time spent at greater client expense, for the same net profit.

But here’s the thing. I did not have a chance encounter with an artist from San Francisco while at the San Diego airport. I didn’t hear or see an ad while in Brisbane that would challenge me, or read about some crazy publicity stunt in their local media. I didn’t get a personal glimpse into the everyday lives of those in Mumbai, or chat with a vender at the local market. I didn’t chase down curious things that showed up in my feed due to location monitoring. In short, what used to “just happen” didn’t happen. I’d be curious if you have noticed the same thing? But were perhaps unable to actually label what was going on?

Of course there are many other things I’ve consciously done to digitally be exposed to wonderous things: signing up for newsletters out of my usual areas of interests, reading voraciously content from new people across the globe. But it can be hard, especially with algorithms that favour serving up content that you’re supposed to like (ie: similar to your existing patterns). These actions actually limit the possibility of serendipity emerging. They’re curated, not browsed. But until we’re in a position to travel more freely and interact with others on mass, I think it behooves us all to consider other ways to purposefully provoke creativity and observe trends outside our own little bubbles.


Am I off base this week, or on to something? Let me know what you think. Leave a comment below or message me. If there’s a podcast or newsletter that you think I might love, simply because it fits the criteria I’ve described here, I’m all eyes and ears. Suggest it in the comments. And if there’s a person that you think I should e-meet, simply because they fit the criteria of “that interesting person Mary would have spoken to at the airport if she could”, feel free to propose an online introduction.

Keep believing in chance encounters. We’ll get back to them soon enough. But until then, be sure to consciously expose yourself to new things, and keep that creativity and trends radar sharp!

Mary Charleson

Leave a Reply

Your email address will not be published. Required fields are marked *

Featured on


Subscribe to Mary’s Weekly
Five-Minute Marketing Tips.

  • This field is for validation purposes and should be left unchanged.