The Art of Assisted Serendipity

Last Updated on April 22, 2024 by Audrey Scott

In your travels, have you ever experienced a moment of a lifetime — an accident of sorts, one never in the plan? Have you ever met someone who would become of great importance to your life, yet you’d never really set off looking for him in the first place? Have you ever experienced some unplanned fortune which upon further reflection seemed at least indirectly connected to choices you made along the way?

This blend of intention and chance, this is life.

It's also the stuff of what I call “assisted serendipity.”

Serendipity: A Definition

Merriam-Webster tells me that serendipity is: “luck that takes the form of finding valuable or pleasant things that are not looked for,” implying that good fortune is in the driver’s seat. Dictionary.com, however, offers a definition more active, “an aptitude for making desirable discoveries by accident.”

The term ‘aptitude' suggests a capability innate or acquired, or even a ‘faculty' as indicated by Oxford English Dictionary. This latter definition suggests there’s something each of us can do to cultivate serendipity. This outlook aligns better with the history of the term and the way I’ve experienced it in my own life.

To the degree there’s any doubt, that’s where the word “assisted” comes in. That is, we must do something.

Serendipity: A History

It’s said that Horace Walpole coined the term serendipity in 1754. The word refers to the tale of The Three Princes of Serendip, the Persian name for what was then known as Ceylon, now modern day Sri Lanka. In the story, the main characters would, by a combination of accident and wit, fantastically intuit what happened to a valuable lost camel. Speaking of the princes , Walpole said, “they were…always making discoveries, by accidents and sagacity, of things which they were not in quest of.”

Assisted Serendipity: A 7-Step Framework

For assisted serendipity, I offer a framework. The structure is much like a problem-solving process but with a twist. What follows is not a recipe or prescription, for the results are never the same.

1. Go…To Engaging Places

The most basic step is to get out. Whether you travel across your city or across the world, that is up to you. The main idea: put yourself in places that are different, where you’ve never been before, that perhaps stretch your comfort zone and build a bit of experiential and emotional muscle.

2. Allow Curiosity to Drive You

Whether it’s travel or networking, allow curiosity to guide you. Allow yourself to get lost, wander with wonder, follow the smell of spices or flowers, check out a street art mural on a wall around the corner. For us, directed wandering — where we have a destination in mind, but are open to never arriving — is one of the best ways to discover, and to set the groundwork for serendipity.

3. Open Yourself Up

Allow yourself to be vulnerable in safe spaces. There will be plenty of opportunity to say no or close down later, but head out the door with the attitude of the beginner's mind. Be open to the new. This includes opening up to other people, too.

An unexpected encounter or connection can be the storehouse of some of life's most fulfilling experiences. There will be plenty of appropriate times to say no. Openness is the magnet that signals that we are receptive of serendipity. Openness as an orientation allows impressions and observations to stream in. From there, filter.

4. Observe

There may be all sorts of serendipitous possibility in your midst. If you don't allow yourself opportunity to notice, it will simply pass you by. Put the camera down, stow the smartphone away in your pocket. Take a breath, be still, be present. With this, notice with all your senses — the scents, the sounds, the textures, the flavors, and the imagery — all to appreciate the patterned and the random around us.

Tuning your observation, you will intuit connections and join threads that may never have passed your consciousness before.

5. Act and Engage

Once you take time to observe, if something strikes you as curious or you wish to understand more, don’t wonder in place. Act on your interest. Go up and ask a question, put yourself in the middle of things, get your hands dirty. Otherwise, you might always wonder, “Was that who I thought it was? Where was that situation going? What were the possibilities?”

The idea of assisted serendipity is not unlike the essence of this quote from the poet Carl Sandburg: “Nearly all the best things that came to me in life have been unexpected, unplanned by me.”

Beware, though, that the beauty of assisted serendipity is the delicate dance of focus and flexibility. If you force too much intention, you may blind yourself to the possibilities.

6. Take Stock and Reflect

Give yourself time to look at what has happened and to take stock. What did the combined forces of intention, chance, and deliberate engagement yield? Evaluate and consider what you might do differently next time. Yet be grateful for what you chose to do this time around.

7. Repeat

There are no guarantees, but the more you exhibit these behaviors and apply these approaches, the more you’ll likely find yourself saying happily “I couldn't have planned it, even if I'd tried.”

Others may begin to comment about how the craziest things always happen to you, that serendipity smiles upon you, that your life is a charmed one.

While chance will have played its role, you'll also know that your actions played theirs.

And that you gave possibility a nudge.

That is assisted serendipity.