Why You Should Plan for Serendipity

April 30, 2014

If you’re a busy professional like me, chances are your calendar looks a lot like a Tetris board. Every minute of every day is accounted for. Some hyper-organization is necessary, of course. How else would business get done? But on a recent trip to Chicago, my colleague Aaron Ferber reminded me of the importance of leaving room in one's personal and work life for serendipity. He shared the following story with the IDEO Chicago studio. It resonated with his fellow designers and me and I thought my LinkedIn readers would enjoy it, too. Here’s what Aaron had to say:

“I’m the vacation planner in my family. My organizational approach is simple: plan every day, but not a single minute. I do enough research so we go to interesting places, but not so much that there’s no time left for the unexpected, because those chance moments are sometimes the most delightful and memorable.

I came across a term a few years ago that perfectly encapsulates my approach to vacation planning: ‘engineered serendipity.’ The notion that you could intentionally design your life to encounter surprises struck a chord with me and reminded me of a trip my wife and I once took to Honduras.

We’d just finished a short stint volunteering at an orphanage and were back in the city of La Ceiba, about to catch our flight home. Before leaving, however, we wanted to buy a hammock as a souvenir. We’d seen lots of beautiful, handmade hammocks for sale by local craftsman during our stay, but our last day in Honduras happened to be a holiday, and all the street vendors were closed. The only place that was open was the mall. The stores there had a few hammocks, but they were mass manufactured, not made by hand, and were much more expensive. Disappointed and running out of time, we gave up and hopped into a cab.

On a whim, I mentioned to the driver that we were looking for a hammock, did he know where we could get one? He paused, thought for a bit, then slowly nodded his head. ‘Si,’ he said, and threw the car in drive without further explanation.

After some time, we pulled up in front of a large, cinder block building on the outskirts of town. It didn’t have many windows, just a single door on the side. The driver slammed the car in park and hopped out without saying a word. My wife and I sat in the back and exchanged worried glances. As our driver walked up to a group of uniformed guys standing outside the building, it dawned on us: the men were police officers and the building was a jail.

After a few very long minutes, the driver returned. He told us they had a hammock for sale. My wife and I looked warily at each other. Was this a scam? Were we going to be shaken down for a bribe? Or should we trust him? Desperate, and more than a bit curious, we got out of the cab.

An officer told us to empty our pockets before entering the building. Handing over our bags and wallets (!), we stepped into the jail, which was basically one giant room surrounded by bars. Dozens of guys were milling around, working out, and playing cards. Spotting visitors, they turned and stared.

The officer yelled at one of the inmates. The prisoner grabbed something, hopped off his bunk, and walked over to us…hammock in hand.

We stood, mouths open, as he showed off his masterpiece. Every bit the salesman, he talked about the quality of the construction, the colorful patterns, and the tassels that ran along each side. The hammock was beautiful, exactly what we wanted. His asking price was higher than we wanted, ‘But’ I said, trying to justify the purchase to my wife, ‘this hammock comes with a story!’ After some haggling, we agreed on a price. The prisoner carefully folded the hammock until it was small enough to fit through the bars. We passed a stack of cash back through the bars and thanked him.

Stunned, delighted, and inspired—with a beautiful, new hammock to boot!—we climbed back into the cab and sped to the airport.

So my question to you is this: How might you engineer some serendipity into your next vacation or into your day today? This could be a simple as taking a new route on your commute to work or asking someone on the street for directions instead of relying on Google Maps.

Who knows, you could find nothing.

But maybe, just maybe, you’ll find a hammock.”

What happened the last time you opened yourself up to serendipity?

(Posted also on my LinkedIn Thought Leader blog)