Photo by Ramaz Bluashvili on

at times the best kept universe   
was my own, no interceding docents   
or guided tours, but a riverine serendipitous   
wandering—waif, naïf.

Leslie Williams, In Me as the Swans

Remote work is wonderful for its flexibility but without a change in work patterns it will crush us with lost opportunities. If people feel the need to book meetings all day, even when working wherever they please, then the opportunities for moments of serendipitous discovery decline. If you have to book a meeting to make a call, then casual and incidental conversation will be lost.

Technology might mitigate this for some, but the losses for many will be deeper. Not all of the context we need to work is available from chat and community, unless we foster the tangential conversations to bring depth of context. Without deep shared context, we can’t understand each other. If parties aren’t working out loud with full transparency, serendipitous conversation is essential to reveal that context.

Over the last few weeks I have struggled with issues in progress on key projects. In each case, the problem was a lack of depth of context exacerbated by distance, In each case, it took serendipitous and tangential conversations to reveal that someone was changing roles, that a key stakeholder was not aligned or that two parties shared a different meaning of a key term.

Naïve wonder is important. Flowing around the problems is important to find new paths, new ideas and new capabilities. Step changes in efficiency can come from inefficient and aimable discovery.

& what if hope crashes through the door what if
that lasts a somersault?
hope for serendipity

Mong-Lan, Elegy

To leverage serendipity we need an intent that guides our attention. We will miss the brief moment if we aren’t paying attention. This intent may be a purpose, a problem or an ambition. That intent need not be at the forefront of our efforts but it needs to be present enough in mind to be able to guide us to what the universe and our connections offer up.

Serendipity demands space and time. Because it cannot be programmed or scheduled, it must come from exploration. Tangents, doubling back, going deeper, taking the time to appreciate something, or more often someone, open up the many winding paths to nothing at all or perhaps a surprising discovery. Serendipity is an outcome of a deep connection in the moment to surface hidden information, capabilities or intentions. We all know love at first sight is rare, most love is developed over long interactions. It flowers from depth of connection, not immediate recognition. Serendipity, too, can be a flash of inspired connection or the outcome of a long slow development of shared context, trust and exchange of information.

Serendipity can take its sweet time to unfold. It may require us to unlearn, to let go or to surrender to a better approach than the one to which we have been clinging so tightly. We may need to admit we are wrong or that a major change is required before we can accept its gift. At other times, we might need to embrace the scary dark of uncertainty, failure and despair before we can see the hand out that we are being offered.

We need to be present to capture the moment that arises when we explore the landscape. Most serendipity does not occur head on. The connection can be upside down, backwards or in passing. Grabbing that moment and not letting it pass is essential to realising the opportunity.

This Valentine’s Day may life bring you a little serendipity and may you be brave enough to grasp it.

At the edge of the forest the thistles
were attaching themselves to the fur of animals.  
What serendipity to hitch a ride to your future.

Stuart Kestenbaum, How to Start Over
Photo by Jasmine Carter on

PS: one for the serendipity of Big Game fans

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