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PROGRESS REPORT

ISSUE #122

The State of Serendipity:
Insulated from Opportunity

Words: Joey Camire, Michael Ian Kaye, & Natalie Berry

Some of you may have caught us a couple of weeks ago at our Fast Track session for the Fast Company Innovation Festival. If you did, thanks for coming. If you didn’t, you’re in the right place now.


The session led to a collective realization here on our team: the topics we presented, The Anomaly of Delight and The Deception of Comfort, are (maybe unsurprisingly) connected. Today, we’re exploring that connection. In what way does our obsession with comfort keep us from experiencing serendipity? How do brands and businesses reinforce this? And what can we do to break out?

The Death of Serendipity

Serendipity. Happy accidents. The bearer of surprise and amusement. A driver of some of the greatest discoveries of all time, from purple dye to the planet Uranus. An essential component of all of our lives. And yet, it’s impossible to create or summon. After all, serendipity is inherently random.


This randomness is often at odds with the structure of our digital environment. Our entertainment, job searches, news, creative inspiration, romantic lives, and more are all strongly influenced by algorithmic oversight. So much of what we see and consume is anything but random; it’s calculated, inevitable, and, often, same.

Trapped in a Cycle of Comfort

If serendipity holds this richness, both from an emotional and innovation perspective, why are we turning from it? Why do we indulge in environments that make it impossible to experience serendipity? It’s because they are more comfortable.


There’s nothing easier than scrolling through a feed that feels familiar. You know you won’t be challenged. You won’t have to get vulnerable. Your brain won’t be activated. Your beliefs or identity won’t be questioned. Put your feet up. Stay as long as you’d like.


In a world that feels increasingly threatening—even if it’s actually getting less threatening in many ways—what could be more appealing than a filter bubble?


It goes beyond the content itself: the platforms the content is on are designed to lull us into a state of comfort by giving us neurochemical hits with each swipe. In a way, it’s brands’ attempt to manufacture serendipity. But this algorithmic serendipity isn't real—we’re just made to think it is.


That comfortable, endless scroll is lucrative for businesses. So, they feed us more of what they already know we like, keeping us in our bubbles. Why rock the boat?


This leaves us trapped in a cycle of comfort. Businesses continue to rely on it because we overindulge in it. We continue to consume it because businesses continue to push it with algorithmic precision.


The issue with staying in this cycle? Nothing new or surprising can infiltrate. We’re depriving ourselves of real serendipity, which also means we’re insulated from opportunities for advancement. As individuals. As businesses. And, importantly, as a society.

Popping Your Bubble

To escape the bubble and unlock the value of serendipity, we must adopt a tolerance of uncertainty, of the unknown. After all, serendipity and randomness are a package deal. And with randomness, you never quite know what you’re going to get.


Let’s be honest, for many of us this can feel very uncomfortable. Because the more you open yourself up for beautiful moments of serendipity, the more opportunity there is to experience the bad, too—the things outside of your comfort zone. Challenging your worldview, experiencing contradictory perspectives, maybe even learning you were wrong about something.


But even those moments of distaste can be instructive: handling unexpected curveballs or enduring unpleasant situations (a random rainstorm, anyone?) makes you more capable, adaptable, and emotionally resilient.


So, how do we step into discomfort in order to invite serendipity into our lives?

One Thing You Can Do Right Now

Craft and commit to a “Discomfort Diet.”

Building a Discomfort Diet

A Discomfort Diet is a conscious effort by a person or company that helps us break out of our comfort zones, increase our tolerance for discomfort, and embrace richer, unexpected ideas and experiences. Feel free to use this worksheet to guide you in building your Diet—it can be relevant across all areas of work and life.


But for those of us trying to pop our bubbles, here are a few thought-starters for your Diet:

  1. Understand what you’re up against. If an algorithm has you in a filter bubble, learn how you can break the algorithm. How much do you really know about how recommendation algorithms work across different platforms? Can you access the data associated with your profiles? Can you research the user-facing algorithmic tools and levers that the platforms have instituted?

  2. Become an agent of chaos. Once you know the ins-and-outs, you can begin to use that to your advantage. What might it look like to throw the algorithm a curveball? How might you adjust your searches? Can you follow different people? Can you be more choiceful about what you interact with and how?

  3. Rethink your defaults. Where do you go for recipes? For design inspiration? For fashion trends? What might it look like to go somewhere else first?

About the Writers

Joey Camire is a Chief Strategy Officer at SYLVAIN. Here, he’s led innovation and brand strategy work for clients including Google, GM, Afterpay, Waze, VF Corp, Bloomberg and many more.


Michael Ian Kaye is the Chief Design Officer at SYLVAIN, working with a diverse set of clients including Walmart, Meta, Kate Spade, Marriott, Stella Artois, Calvin Klein, IMG New York, Fashion Week, and The Information.


Natalie Berry is the Editorial Lead at SYLVAIN. She works behind the scenes to produce every edition of this newsletter, as well as all of the SYLVAIN content you know and love.

About Progress Report: The State Of

Progress Report is a bi-weekly newsletter of business considerations, cultural conversations, and fun recommendations from around the world and web.


In this special series, The State Of, we dive a little deeper into one topic that’s urgently impacting businesses, brands, or consumers.

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