Serendipity: Optimize Your Odds For It

Plan For Randomness

optimize for serendipity

Are we familiar enough with the nature of serendipity that it becomes wallpaper we don’t notice much?

Is it loitering on the sidelines taken for granted, surreptitiously nudging us to not move on and put our attention elsewhere? To other phenomenon, strategies?

Have we forgotten to really pay attention to this mind-bending, life and work-changing thing that’s rich and complex enough to be one of the ten most difficult English words to translate? That would be a shame.

How Do We Safeguard Our Odds For Serendipity?

Serendipity is to be cultivated. Invited. When we fail to realize that, we fail our business and our marketing efforts. When we consider personalization in search and the semantic web, serendipity is ever more critical. Do we want to reach towards our highest potential or make a futile attempt to keep safe, over-control, force things to go the way we think we want them to? Innovation comes from maintaining flexibility. Too much order closes doors. Limits the possibilities available. Thus we get the urge to move into ideas like (un)strategy and (anti)discipline just to go against our own rigid tide.

Kudos for openness, collaboration, partnerships, shared ideas, experimentation, loose structure, inclusion, creative process, unanswered questions. [clickToTweet tweet=”Plan for that. Meandering down detours, side roads and alleys. Seeking serendipity. ” quote=”Plan for that. Meandering down detours, side roads and alleys. “]

“Selfishness kills serendipity. We create more luck through generosity.” Colin Raney

Serendipity is the underground original disruptor, the thing that is always quietly, just barely hiding out in our peripheral vision waiting for the moment it can present itself and throw us off guard, surprise us. Hand us something new and unexpected. Make us scratch our heads in happy wonder.

Serendipity will turn nothing much into something that feels like a charm, arriving at fruition. Share on X It disrupts because it cannot be tamed. If we took it out of our equations, things would flatten out, lose vitality and we would be missing something crucial; one of the best things we’ve got lingering around waiting to happen. That thing that feels like magic. That we love oh so much. So then, why isn’t it continuing to be a more prevalent part of the current (online) conversation? Are we forgetting to notice and taking it for granted?

Here’s one: I don’t believe you would be reading this right now if my father hadn’t switched from piano to timpani in order to gain entrance to Juilliard in the 1940’s.

A Tree Falls

It’s not quite like if we don’t notice, it won’t happen. But if we don’t notice it might as well not happen. Because who will be there to catch the tree? Who will benefit from the experience? The observation? We risk being nearsighted to relationships and connections of things and time, context, place. We risk being unprepared. And the serendipitous thing goes by un-nurtured. We miss out on learning to operate in a way that invites increased innovation via increased serendipity.

We know a lot about how it works. We have respect for it. Awe, even. Systems and strategies (or un-strategies) (anti-disciplines) have been designed to accommodate, encourage it. We have incorporated serendipity-centric words and terms into our vocabulary like “Serendipiter”, “Super-Encounterer” “engineering serendipity” even “Serendipity Economy”.

But is it really part of our daily awareness in a way that will give us the most chance of benefiting from it? Likely not.

Take this article. I’ve been spending a lot of time researching, reading, watching videos purposefully not rushing. It’s occurring to me now that I’ve been making the process itself of writing this serendipity-friendly. The odd random thoughts that pop up, the stories that come to mind have time to percolate and gel. Detour. Surfing the web, following trails that lead me to obscure texts, the odd slideshare or study. Wandering off on tangents. Living the mundane aspects of daily life. Who knows? Maybe by the time I’m done, some serendipitous story will have materialized so I can prove that if we make the space it will happen and we’ll notice it when it does.

serendipity definition
Merriam Webster

The Digital Age

In the definition of digital information-based serendipity, serendipity is:

1) the finding of unexpected information (relevant to the goal or not) while engaged in any information activity,
2) the making of an intellectual leap of understanding with that information to arrive at an insight.”

“Considering the history of serendipitous discovery, we see that success of serendipitous discovery is not just the find itself, but being able or willing to do something with it. …consider ways where we can enhance the likelihood and potential for serendipity and insight: for example, through surfacing connections, play, enhancing domain expertise, and mechanisms to share discoveries.”

“…By taking a broader view of serendipity than simply having a serendipitous insight, but by looking at also what it means to have a prepared mind and an infrastructure to support discovery, we have presented, we think, a more holistic picture of serendipity, and thus perhaps ideas that may improve the creativity, innovation and discovery process.”

“Discovery Is Never by Chance: Designing for (Un)Serendipity”, Paul André, m.c. schraefel, Jaime Teevan, Susan T. Dumais

Is Serendipity Important?

Business needs it. Marketing needs it. A life well-lived life needs it. It adds to the mystery and magic of our universe and it adds significant value to all our endeavors. Even the most seemingly insignificant.

It makes everything potentially important. Because we never know where value may come from. Or what pieces will fit together.

Allowing it to thrive can also take some courage. A release of rigid plans and structure is involved. It requires flexibility, a sort of relaxing-into flow, seeing what might happen next. And trusting that whatever happens next encases a world of possibility. It requires being in the moment, living each moment as if it counts. Embracing uncertainty. Residing in not knowing. Being willing to stay with and make use of whatever may arise. Some Zen.

“Dr. Erdelez came up with the term super-encounterer to give us a way to talk about the people rather than just the discoveries. Without such words, we tend to become dazzled by the happy accident itself, to think of it as something that exists independent of an observer. …But discoveries are products of the human mind. …As people dredge the unknown, they are engaging in a highly creative act.” (bold, mine)

Pagan Kennedy “How To Cultivate The Art of Serendipity, New York Times

Joichi Ito, Director MIT Media Lab, in a panel called “The New Serendipity,” talked about retaining his “beginner’s mind” . He said of his directorship at MIT that he aims to capture serendipity. “You don’t get lucky if you plan everything — and you don’t get serendipity unless you have peripheral vision and creativity.”

Marketing and Serendipity. How Do We Use It In Our Businesses, Our Work?

When serendipity was a concept in its infancy, newly named, it was heralded and rewarded as a skill rather than merely a stroke of good luck. A skill that can be developed. One that is needed in marketing today.

Serendipity isn’t just a happy accident. It’s malleable. And we aren’t merely observers, we’re participants, directors. We benefit from its whispers of unexpected opportunity. We can propagate instances and encourage results born of them. We can cultivate serendipity in our attitudes and behaviors, our perceptions. And by accepting that we may not be able to explain everything that happens. But we can understand how to do some nudging of our own, create and watch out for connections, clues. Remain creative.

A chance is an event. We either respond to it or not. Serendipity is a dexterity. Put them together to make something of an unexpected circumstance. Foster the quality of recognition. To gain insight.

meaning of sagacity
Merriam Webster & Free Dictionary 

“Serendipitous discovery plays a huge role not only in scientific advances, but also in major breakthroughs in marketing strategy. With more data open to marketers than ever before, marketing analytics can now play an even bigger role in revealing unanticipated breakthroughs that propel your business. And even though planning for serendipity may sound like an oxymoron, there are ways to optimize marketing processes that boost your odds of hitting pay dirt. Mining for these kinds of surprises is more important than ever for marketers. […] Truly serendipitous discovery is an iterative process of exploring unknown territory, not just confirming a hunch with a one-off view into the data. Better insights result from suspending your agenda and parking your preconceived notions long enough to let the machine spark your intuition algorithm.”

Joshua Reynolds,“Intentional Serendipity: How Marketing Analytics Trigger Curiosity Algorithms And Surprise Discoveries”

“Serendipity is the process through which we discover unknown unknowns. Understanding it as an emergent property of social networks, instead of sheer luck, enables us to treat it as a viable strategy for organizing people and sharing ideas, rather than writing it off as magic. And that, in turn, has potentially huge ramifications for everything from how we work to how we learn to where we live by leading to a shift away from efficiency — doing the same thing over and over, only a little bit better — toward novelty and discovery.”

Greg Lindsay

So again, I don’t believe you would be reading this right now if my father hadn’t switched from piano to timpani in order to gain entrance to Juilliard in the 1940’s.

My father, Ivan Fiedel, found out that Juilliard, in NYC, was overrun with piano applications but short on timpani students so that’s how he got in; by side-shifting and taking his chances. And he knew it meant he’d study with Saul Goodman, an opportunity in itself. But in order to continue his study of piano composition because that really was his instrument, he found his way downtown to Erich Katz, a professor at the New School for Social Research. If my father hadn’t experimented with timpani in order to get into Julliard, he might not have needed to seek out another teacher elsewhere. But Erich also became a dear friend and mentor. His unconventional teaching approach and dedication to improvisation was a perfect match for Ivan. And in fact, Erich was instrumental (pun intended) in shaping my father’s teaching philosophy and his use of improvisation to form the core of his work. “Being educated by [Katz] involved not only a verbal-intellectual process, but the body and spirit as well.”  Seems to me, in telling this story that there’s something additionally meaningful in Erich’s dedication to improvisation. I’m telling a story of serendipity about people who knew how to embrace it. Improvisation, the motherload. Serendipity is at the heart of improvisation and is intrinsic to creativity and the creative process.These were only the first moves in a cascading serendipity roll that spans 68 years, give or take. Share on X

In what I imagine to have been a pioneering mood in 1959, Erich moved to Santa Barbara, California, a very quiet, somewhat isolated town at that time. Maybe a less mysterious choice when we note that he became entrenched with the now famous Mountain Drive community up in the foothills where wine stomping, innovative minds and musical bohemians had their own haven far from the conventional mores of town and were establishing their own methods to approaching life. He lived in a handmade house built of cement blocks nestled into the steep mountainside and there continued his work. The subsequent letters that arrived to my parents about the utopia he’d discovered and become part of intrigued them, made them long to visit. For all the years of my childhood, they had a singular fascination with Santa Barbara, their imaginations and dreaming minds utterly captivated. Our family visited Erich in Santa Barbara when I was around 9. It was my parents turn then, to fall in love with the small town sandwiched between the ocean and mountains. And…

Twenty-two years after Erich passed away, my parents relocated from NYC to their west coast dream town. Sadly, less than a year later in mid 1995, my father was diagnosed with terminal cancer and died having never gotten but a few years to enjoy his new home.

Now here’s where we fit in. When my father was first diagnosed and given a prognosis of three months, our family was devastated and in our typical Fiedel manner we each felt we had to do something. We quickly scrambled. My husband, Doug, and I, relocated temporarily from the Boston area to help my parents. The expectation was that we’d be here for three months, but instead, to our delight, my father continued to live. That was the start to our own love affair with Santa Barbara. When my father died two and a half years in (he beat the odds again), we decided we wanted to stay. We founded our company here and put down permanent roots in this town that has become a legend in our family.

We were led to something completely unexpected, unplanned and surprising. We would never have dreamt of moving at all, much less across the country to Santa Barbara had Erich and later, my parents not done exactly that. And particularly, had my dad not suddenly become ill creating a need that pulled us into proximity. My parents would never have moved here had Erich not written those letters they loved. It was no deterrent that he was no longer alive by the time they did. And my dad may not have met Erich if he hadn’t applied to Julliard as a timpanist. So we’re here due to the trail of changed plans, relationships, careers, desires and events unrelated to our own life trajectory but instead related to my father’s youth and death and his mentor. We serendipitously landed in one of the most wonderful places I can imagine.

Wait. There’s more…
When we arrived in Santa Barbara, my brother’s ex, who lived in the fair town of our story and we are still close to, held a dinner in our honor to introduce us to a small group of her friends. It turned out that one of the women, who had lived in Santa Barbara for at least twenty years and who was randomly seated across from us at the dinner table had, decades earlier, lived in the Boston area where we’d hailed from. Not only that, but she had taught elementary school in Newton, the suburb where we lived, back in the early 70’s. It next became revealed that the school she’d taught in was the school we had refurbished and transformed into our home and our studios in 1988. The Claflin School Studios in Newton, MA. But not only that, she taught in the very same classroom that was now our home. Huh?

At that time we’d lived and worked in the converted 1950’s elementary school that had been abandoned and boarded up for almost a decade before we became designated developer by the City of Newton and renovated and repurposed it . The project ran from 1985-1988. Not only that but I’d co-founded and spearheaded the artist live/work condominium development project. We’d had first pick of all the classrooms because of that. Guess I picked well. No one present at the dinner even knew she had taught school back then. What were the odds for a chance connection like this? If felt as though fate had followed us across the country.

There’s one more chapter- about eight years later, I found out that someone I’d met through an entirely different channel, who was an influential and important person in my life in Santa Barbara, is the x-husband of the woman who’d taught in our classroom-home in Massachusetts. They’d been married during the time she taught there. Go figure.

Serendipity. A circle of connections and opportunities.
End Story

So What Does Serendipity Really Mean To Us?

I’ve read dozens of articles about serendipity now and I’m still “collecting strings” to quote Gay Talese, author of the book “New York: A Serendipiter’s Journey.”

“The term “serendipiter” breathed new life into Walpole’s word, turning serendipity into a protagonist and a practitioner.” Pagan Kennedy

(Horace Walpole was responsible for forming the word in 1754. He explained to a friend that he’d made an unexpected discovery in reference to a Persian fairy tale, The Three Princes of Serendip. The princes were “always making discoveries, by accidents and sagacity, of things which they were not in quest of”. And so, the word came to be.)

If there’s one thing that stands out in all these strings I’ve collected, it’s that we play a part in our own serendipitous successes and it’s advantageous to do so.

“Serendipitous people are more fearless about trying something new. Instead of giving in to worry about what could go wrong, they think, “Isn’t that interesting? I’d like to give that a try.”

Rebecca Webber, Psychology Today, “Make Your Own Luck

How Do Things Fall Into Place?

Back when we were starting Fat Eyes, Doug and I were both members of the Masters Swim program here in Santa Barbara. We spent several hours every week drenched in swim interval training. It was an intense, even painful workout at times, but some relief came with the natural camaraderie and necessary cooperation with the other swimmers, especially the ones in our lane (we were grouped by speed). In each lane, it was a lineup with a leader and followers all carefully choreographing the timing of their laps according to the times on the big clock matched with the workout on the blackboard.

There was also something kind of funny about the friendships we made in the pool. Wearing Speedos, faces covered in goggles and heads in bathing caps caused us to lose some of our individuality. There weren’t any indicators to identify our style, our street identity. It was always amusing to not recognize a lane mate in the supermarket or even in the parking lot at the pool. Clothes and hair make such a difference. But the intense workouts that we executed together were bonding and friendships developed.

There was a guy. A young man who swam in Doug’s lane (the fastest lane). One evening during a short break standing around in the pool, we were chatting and happened to mention that we were starting a business. He somewhat vaguely let on that he worked for a company based in Texas and they might be looking for some help on a project. He was a software application programmer as it turned out. Over the next few workouts it became apparent that the project he was assigned to still needed user interface design. He asked for our phone number even though that wasn’t our area of expertise at the time.

We didn’t expect a call but our curiosity was stirred. We didn’t really know much about him other than that he was a strong swimmer and loved his wife who swam in my lane one over. It wasn’t really the kind of work we were envisioning for Fat Eyes, but we decided to be open.

As it turned out, he did call. We met with he and his partner, both of whom turned out to be delightful utter geniuses and we left that first meeting in a kind of shock and information overload. They were engineers, after all. And they didn’t just have some work. They had a ton of work. And the work was exciting. The segments we designed for over the period of more than a year gave us just the chance we needed to refine our interface design chops and get Fat Eyes solidly off the ground. They helped us start our company without meaning to or maybe even realizing it. And all they had to go on were our strokes, ability to watch a clock and be relatively friendly. End Story. You never know. Share on X

Encounters, Plan Changes, Random Consequences

• “Our mind abhors these serendipitous explanations, and searches for convenient patterns instead. Ask for the keys to career success and you’ll get logical explanations, recommendations, pathways and approaches. Then ask someone how he or she became successful and suddenly it becomes a story of serendipitous encounters, unexpected changes in plans, and random consequences. It does not make sense to ignore this basic fact about success any longer.

• We like to think that success comes from predicting trends, analyzing data, gaming out strategies — from using some sort of logical approach. But if it was that simple we should have solved the mystery of success long time ago — and we haven’t. Instead serendipity is what sets us apart — since that is the only way we can discover an approach that is not obvious or logical.

• Your organization, career, even life can change in a single moment. Make sure to seize it.”
Frans Johansson, author of “The Click Moment”

The Ethereal Layers Of Measurement In Relation To Serendipity

Daniel W. Rasmus, Fast Company writer, former Director of Business Insights at Microsoft Corporation and author of Listening to the Future and Management By Design, is a strategist and industry analyst. His model, The Serendipity Economy, articulates the usefulness of accidents and their applications in business and on the digital networks.

The Serendipity Economy …requires awareness, patience, and perseverance as ideas arise and as innovations gestate, mature, and evolve. Rather than looking always for better, faster, and cheaper, organizations can capture and quantify value that arises from the random encounters of individuals with each other, or with ideas, that lead to innovations that no enterprise architect or ROI calculation could anticipate.”


“All collaboration technology, innovation processes, improvement programs, and most marketing efforts result in serendipitous activity. The outcomes from open, cross-organizational networking can’t be predicted, nor can the time to value or magnitude of ideas generated by such networks be anticipated. Business leaders who actively monitor, document, encourage—and protect—serendipitous activity will be able to attribute much higher returns … than those who focus only on reductions in cost and time.”
Daniel Rasmus

Value For Business And Marketing

We have consensus on value but can we measure serendipity? Do we want to? Do we really need to? The answer may be that it begs to not be measured with any kind of precision. Its uncanny nature asks to be let alone, given the spaciousness to surprise us in its almost magical properties.

The Serendipity Economy is an economy of facilitated accidents. It is an economy unfathomable at the macro scale without the Internet. Innovation and serendipitous activity, by its nature, is limited to those who are connected. In the past, it was impossible to experience a serendipitous event without physical proximity. Digital networks increase the bandwidth for serendipity. It creates a larger context for the exchange of ideas that might lead to something of value.”

 “We let the Serendipity Economy happen to us because it falls outside the experiences we have been taught are measurable. And because we aren’t looking closely, we put all of those “intangibles” into a conceptual bag together and look at them as extras when we can find a measurement, and too difficult to measure when we cannot.”
Daniel Rasmus

Serendipity In Semantic Search

David Amerland, in his SEO-tips article “Designing Serendipity In Semantic Search” gives us a casing for practical applications, things we can do ourselves to promote the vitality of serendipity in our business. To reiterate, in today’s world of personalization in search and the semantic web it’s ever more critical. He shows us that it’s possible to execute groups of incremental actions that compliment each other and set the right stage for possibility and opportunity to increase. In his words,

Here is what you need to do:

• Have a data-dense presence on the web that makes it easy for Google to extract entities from your content. Make sure, for instance, that your website, your Google+ presence and your Twitter account are easily mined from your online activities. Ensure that content you share is surrounded by enough high-trust data (links to trustworthy sources, cites authoritative websites, etc) for Google to feel that it’s an important piece of information that must be included in search.

• Deliver value in every item of content you create that helps bolster your online identity (see point above).

• Create wide networks of online contacts that you use to find content (people you follow on Google+, Facebook and Twitter, for instance).

• Generate engagement in your content through the social web. Commenting, sharing and ‘smaller’ interactions such as Re-Tweets, Likes and +1s all have an impact that becomes part of the “social proof” of a piece of content.

• Add context– don’t just create (or curate) great content. Add the kind of deep, detailed information that helps it link to trends, establish its freshness and allows the end-user to establish a sense of its value in relation to the time of its publication.

• Create content that resonates at an emotional level with your audience. Comments, their frequency, the type of comment (positive or negative) and its length, who made it, when and in what context are all signals that serendipitous discovery in search can use to help serve your content to a searcher.

Bottom line, content that’s created only for marketing, that fails to support and enhance your digital identity, that ignores the emotional touchpoints and needs of its prospective audience and which has no impact or relation with anything that’s happening across the web (or even across our social networks and affects us) is unlikely to do very much for you in terms of search, branding or reputation. Follow the six points above however and you will find your business getting attention from the most unexpected quarters at almost negligible cost to you.”

David Amerland

A Treasure Called Serendipity

Serendipity is one of humanities treasures. Share on X Its likelihood is increased in today’s online connected world. With the tremendous opportunities for new relationships, cross-pollinating concepts, idea sharing, collaboration, in search, social media and business itself we adopt it as something to value and safeguard. But we can go farther than that. When we fully integrate serendipity into our standard operating procedure it naturally becomes intertwined in all aspects of our business. And of our lives. My favorite part of the following quote is “Build a tangled bank.” The messy gold we store is a kind of currency. Collect and spend it wisely.

“The patterns are simple, but followed together, they make for a whole that is wiser than the sum of its parts. Go for a walk; cultivate hunches; write everything down, but keep your folders messy; embrace serendipity; make generative mistakes; take on multiple hobbies; frequent coffeehouses and other liquid networks; follow the links; let others build on your ideas; borrow, recycle; reinvent. Build a tangled bank.”

Steven Johnson 


* Don’t miss any of our blog posts! Subscribe at the top right of this page.


* Please follow the Fat Eyes Blog Collection on Google Plus.

* Would you like to be included in my Google Plus Notification Circle?
If you would, please visit the invitation and let me know in the comments with a +mention of my name. Thanks!

Pre-remix photo credit: Copyright: Gajus


  • author's avatar

    By: Gina Fiedel

    Gina Fiedel is the co-founder/owner of Fat Eyes Web Development. After a successful career as an artist and transitioning into electronic media in the early 90’s, she then founded Fat Eyes in 1998 to bring those skills to the web with her husband, Doug Anderson. Being engaged in business has created gratifying opportunities for communication and new inroads towards making a contribution that counts. You can learn more about Gina on the Fat Eyes Who Are We? page and Gina Fiedel Story.

  • author's avatar