Dissecting Serendipity

(For the next few posts I’m going be sorting through some thoughts on Serendipity. I proposed a panel around the topic because it seemed like a good way to force myself to dig deeper into the idea. You can find all the articles here.)

Where to begin?
Serendipity is a difficult idea to wrestle with. On the surface, it’s a fortuitous turn of events that leads to an unexpected outcome. The mechanics that create this turn of events are much more nuanced and complicated that you might expect. The existence of serendipity is indisputable, yet it’s occurrence is unpredictable. So much of our behaviors and culture are built on the idea of serendipity, it’s probably worth digging a little deeper. (There is that idea of blind luck, like buying a winning lottery ticket, but that’s not what we’re after here.)

To plow an even field through this topic, it’s probably best to begin at the beginning (sorry). I’ll spare you the etymology and the story about the Princes of Serendip, though I might be the first (almost every piece I’ve read has yet to resist it.)

The Definition
On the analytic side of things, serendipity is a collision in your mind that requires three main ingredients; pre-existing knowledge, behaviors that encourage you to see new patterns, and, most importantly, stimulus that reframes what you’ve known to see something new. An over-simplified equation it might look like this (my apologies to the field of graphic design).


There is an ocean of nuance in each of the pieces of this equation, but these seem to be the main tenants. I’ll dig into the nuance later, but this diagram helps me organize a lot of the axioms around serendipity. First, it builds off what you know. (Which means experiencing serendipity is completely personal; no one organizes all his or her knowledge in the same way.) Second, certain behaviors better prepare you to recognize or invite serendipity. Finally, it’s triggered by an unanticipated experience; so we can’t predict when it will happen, we can only prepare in hopes that it might happen.

At the heart of serendipity is idea of recombination; taking what we thought we know and adding additional inspiration to reframe what we know. In this moment, we might find new insight from past thoughts or a new avenue of exploration. Ironically, because this reframing seems to play on some singular mind chemistry, serendipity isn’t a group experience. But, without the collective to inspire new thoughts, serendipity would be almost impossible.

Beyond the Definition
After we dissect the idea of serendipity into its working parts, it’s really interesting to think about the more spiritual side of the idea. It’s one of those ideas that exists through the magic of who we are as humans and how we learn about our world. To prepare for serendipity invites some of our best human qualities. We need to be insatiably curious, optimistic, diligent, and weather a bit of blind faith – these are the lenses that encourage us to find new perspectives.

Through this research, I’ve found that the process people use to prepare for serendipity is very similar to a design process. Great designers steep their minds in a problem and, through their creative process, tease out something beyond what they knew. They prompt themselves with different stimuli, they share their directions which shapes their environment. They don’t know the end when they begin. Both of these processes invite us to learn and experiment with the intention of arriving at a new idea.

Roger Martin has written about the idea of an opposable mind. He describes an ability in successful leaders to hold conflicting ideas in tension, refusing to let a single idea prevail. (Not surprisingly, artists and designers also work in tensions.) Preparing for serendipity really requires us to navigate tensions in a similar way. To invite Serendipity, we’re asked to…

  • Commit to a direction yet remain spontaneous to new opportunities.
  • Lose ourselves in the problem while retaining some mental distance from the work. 
  • Become an expert in our field while finding patterns outside our industry. 

So this is what I’m working through; I’d love to hear *any* thoughts and reactions. There is no shortage of research and books in this area. I’ll try to note/publish everything I’ve encountered and reference the thinking where I’ve found it. Beyond understanding how to prepare for serendipity, I’m especially interested in its parallels to the design process. I’m also curious in how the way we approach serendipity might be changing in our very connected world (this later interest is the subject of the panel I mentioned at the beginning.)


  1. Great first post on the topic. I’m sure you’ll get to it in time but I’d love to hear more on: Ideo’s office design as a ‘serendipity engine’. How dorm rooms, startup accelerators and coffee shops can increase serendipity. And what rituals we can take on day-to-day to increase serendipity.

  2. Great post! I work in the field of social platforms (enterprise specific), but I’m super interested in filter bubbles, network filters, interest graphs, homophily and serendipity. As platforms like Facebook learn more about its users and can target advertising based on your social graph – where does serendipity come into play? Repeatable, predictable outcomes mean greater business efficiency. There has been a lot of chatter about serendipity lately – but maybe it’s just nostalgia for a world we don’t live in anymore.

  3. Hey Chris & Peter, thanks for your individual comments.

    Peter, I’ll try to do some thinking & write something around serendipity and collisions. It’s definitely something architects think about a lot and seems baked into the curious nature of IDEO. I think beyond the brilliant randomness that can live in all the places you’ve highlighted, I think there’s something about sharing your interests with other people. I touch on it a little bit in this post around exploring and committing. I think in places like dorm rooms, and accellerators (and IDEO), you see people committing to the work they’re doing, and because there is this open ‘publishing’ of intent, others can learn and play along.
    More here: http://colinraney.com/2013/02/exploring-vs-committing/

    Hey Chris,
    I think what you’re working on sounds really interesting. If you have any links or thoughts I can read more about, I would love it. I think Facebook and Google are doing a horrible job of designing for serendipity; they’re editing out the things I don’t want to see. So, in essence, they’re cutting down on my chances for recombination, the same holds true for “smart new sites.” Ironically, I feel like when these sites “design for serendipity” their analytics choke any of the beautiful randomness out of things. But maybe you’re seeing something different?
    I’ve written a little about these things here:

    Thanks to both of you for the comments!

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