“How much can you expect the unexpected before it becomes expected”

Writing a book is really an exciting process! You dedicate your time and energy long term to create something, which you want to share with other people. I have done it once in 2014, but at that time my schedules were tight and my understanding about serendipity, creativity and related topics was not matured.

Fortunately, just now with my “Serendipity Unleashed – Hidden Wisdom of the Jesters” book project I have no time constrains, my understanding has deepened and  I feel confident that my legacy is worth of documenting to a wider global audience. Legacy, are you kidding me? Indeed, we all have our own legacy and we all should be proud of it!  In my case it is my life-long dedication to try to understand creativity, and especially my insights of 20+ years of serendipity research.

I was never really interested in pursuing an academic career and preferred practical consultancy with hands-on activities. Perhaps for that very reason, my dedication and curiosity to study topics like serendipity and creativity have lasted so long. These insights and perspectives had enough time to mature — it was a hobby for me, not part of my daily work. Now, for the first time in my life, I have the opportunity to fully concentrate on writing, and magical things are starting to happen. New perspectives begin to emerge, encouraging insights just pop up — I’ve found my own flow state! It’s both inspiring and rewarding.

This week, I felt the urge to dive deep into the philosophy of serendipity and the very fundamental questions surrounding it as a phenomenon. I’ve already drafted a manuscript chapter about serendipity for my book, but this is an addition I’ll use to improve that chapter. This might turn into a lengthy blog post, but follow along — it’s part of my legacy in serendipity research.

In 20+ years I have presented my ideas in all kinds of scenes, from small workshops to large global conferences with hundreds of listeners. I learned that the best way to start a presentation is to first ask my audience. “Do you like surprises?”  In 90 % of cases someone from audience raises the question: ”Bad or good surprises?” And exactly that proves my point, we as human beings want to know what to expect, surely all of us love good surprises! Not so many like the bad surprises….and here we come to very basic philosophical question of serendipity! To clarify, my answer always is: ”Never mind the end result, just do you like surprises?” And then I see always certain hesitation from audience about how to respond.

I learned that the best way to start a presentation is to first ask my audience. “Do you like surprises?”  In 90 % of cases someone from audience raises the question: ”Bad or good surprises?” And exactly that proves my point, we as human beings want to know what to expect, surely all of us love good surprises! Not so many like the bad surprises….and here we come to very basic philosophical question of serendipity!

There are always people who could be called ‘surprise -lovers’, and then there is another group, the ‘surprise-haters’. For my audiences sometimes there is as much as 90 % ‘surprise lovers’ sometimes 90 % ‘surprise haters’ – and everything between these. You can imagine how I can feel the different energy and excitement even on the podium with different audiences!

Let’s deep dive to the topic.  As always, when it comes to life’s fundamental truths and philosophical questions, we must draw on ancient thinkers—some things were already pondered long ago.

Plato (427–347 BCE) introduced the paradox of intentional research: “It is not possible for man to seek what he does not know because he does not know what he should seek” This statement shows the limit of seeking the unknown, contrasting with serendipity’s ability to discover valuable insights unexpectedly. Plato’s wisdom helps understand how knowledge emerges beyond conscious aims, aligning emphasis on valuing surprising observations.

On the other hand, Heraclitus’s (circa 535 BCE to 475 BCE) wisdom: “If you do not expect the unexpected, you will not find it” is another intriguing perspective, which needs further elaboration. He is saying that you need to be open to surprises to stumble upon them, which fits serendipity beautifully: you don’t find treasures unless you’re ready to notice the unplanned.

The most demanding prompt for our think-tank conversation might well be a question I first asked a decade ago.“How much can you expect the unexpected before it becomes expected?” It is a natural question anyone could ask, but it has a strong philosophical twist. I have started to call it a serendipity paradox. Let’s e try to find some clarity and understanding between it and these ancient wisdoms.

Heraclitus is saying you need to be open to surprises to stumble upon them, which fits serendipity beautifully, you don’t find treasures unless you’re ready to notice the unplanned. But my “serendipity paradox” – twist takes it further. If you follow Heraclitus and start expecting the unexpected, what happens when you get too good at it? Does the “unexpected” become predictable, like a routine surprise? My paradox suggests that over-expecting might dull the edge of true serendipity. So, it’s a question of finding the balance!

Imagine you’re primed for surprises—you spot them everywhere. But if you’re always on the lookout, are they still surprises, or just part of your script? It’s almost like over-preparing could blind you to what’s truly unexpected, because you’re locked into guessing what the unexpected might be. Isn’t it?  I call it a feedback loop.

I believe this builds on Heraclitus by exploring the limits of his advice. He’s right that openness is key, but I am asking: how open can you stay if expectation takes over? I think my statement is a useful philosophical nudge, especially in times when serendipity as a definition has been diluted by so many commercial endeavours!

For me “How much can you expect the unexpected before it becomes expected?” is a natural evolution of Heraclitus’s insight, spotlighting the tightrope between preparation and genuine surprise. In the context of  serendipity and innovation, it’s a wise question to ponder—too much expectation might box you into the predictable, while too little leaves you lost.

For me “How much can you expect the unexpected before it becomes expected?” is a natural evolution of Heraclitus’s insight, spotlighting the tightrope between preparation and genuine surprise. In the context of  serendipity and innovation, it’s a wise question to ponder—too much expectation might box you into the predictable, while too little leaves you lost

We may also ask: “At what point does anticipating the unexpected become its own form of expectation?”  If you begin to expect the unexpected regularly, are you still open to true serendipity, or have you started anticipating it so much that it loses its magic? The more we consciously anticipate the unexpected, the more we might inadvertently shift it from being truly “unexpected” to a regular part of our mindset, thus altering its spontaneous, serendipitous nature.

This connects with the Plato quote as well, “It is not possible for man to seek what he does not know because he does not know what he should seek”. When we try to predict or expect the unexpected, we might limit the very discoveries we aim to make, because we no longer allow space for the truly unknown to surprise us.

My serendipity paradox also speaks to the delicate balance between openness and expectation. I love Agathon’s idea (ref Aristotle) that “Art loves chance, and chance loves art.” which ties into this by showing how sometimes the creative or unexpected sparks of art only arise when we relinquish our need to control or predict what will happen. When we expect serendipity, we may unintentionally start shaping it to fit our preconceived notions, which defeats the essence of the original, unanticipated discovery.

I believe this added perspective illustrates how serendipity overcomes Plato’s paradox by valuing surprising observations followed by correct interpretations. This contrast enriches discussions on innovation, showing knowledge can emerge beyond conscious aims, aligning with our emphasis on being open to the unexpected.

I sincerely hope this blog highlights the inherent paradox in expecting the unexpected, raising the question of how much openness is too much – at which point does it start to undermine the very surprise that makes serendipity magical?

 

  • This blog was partly inspired by Pek van Andel’s excellent presentation titled “LASERENIDITIE: Leçons de l’inattendu,” (Lessons from the Unexpected) given on January 27, 2020, in Toulouse.

 

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Serendipitor

One could describe me as an Explorer of my personal life, since I have been there – seen that, so many fascinating topics and projects over the past decades. I am the founder or co-founder of seven different companies since 1984 .- one could use the term “serial entrepreneur”, but I personally don’t like to be called that way. I believe that my life is a journey – and even though it sometimes looks like I am wandering around, I have a solid feeling that I am not lost. Read more

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