Serendipity as a strategy: how cultivating luck allowed me to bump into a Googler on a beach, a UN representative on a flight and an eccentric Russian woman on a road trip in North California

This is about cultivating luck, following our gut and looking for signs around us. It’s about how over-planning can prevent amazing connections and opportunities from popping up. The kind of opportunities businesses could never plan for even if we wanted to.

Recently, I’ve been reflecting on the opportunity costs that come with planning so much there is no room for luck to emerge. After a series of random encounters with great people, I’d like to share a few stories. I hope they will offer a new perspective on living free-range.

STORY #1: How I bumped into a Googler whilst walking down a remote beach

Early Saturday morning I was strolling down a beach in Bolinas, California. It was very quiet and I saw a girl writing her diary, with her dog playing by her side.

We started talking and quickly found a lot in common. From relationships, to life circumstances, work, values and beliefs. Lots of coincidences. We hit it off straight away and chatted about the new chapters in our lives and how we were both in Bolinas to reflect for the weekend.

This lovely person’s name is Kelly. She’s a soon to be ex-Googler where she works a lot with facilitation. She’s now embarking on a new journey trying to discovering what she truly wants from life and is trying all sort of new things, starting with a Yoga teacher training course in Peru. She’s on a mission to really figure out what makes her tick.

We chatted for a good hour and that night had dinner in a little local restaurant where more and more shared interests and coincidences popped up. A week after meeting we had lunch together at YouTube’s offices in San Bruno and we’re now talking about a couple of projects that we could work on together in the future.

LESSON #1: Being real beats being a role. Why we hit it off.

Walking to the BART after lunch today I reflected on what made this spontaneous friendship possible. I think we connected on such a personal level because we met as people. Just a genuine desire to know somebody for who they are right now, no agenda or assumptions based on the past. It’s just nice to get to know somebody new without judgement. Authenticity is a natural filter I think and it allows us to connect with like minded people.

I’m on a bit of a high after our meeting and choose to see it as a sign that this new way of living is right for me at the moment. This was one of those experiences which make travelling so special. Luckily, it’s an example of something that seems to be happening to me more and more.

STORY #2: I stopped for a pee on a roadtrip, and ended up taking part in a workshop in a Russian cafe

This is perhaps the strangest of these three stories and it happened the day after meeting Kelly. I was feeling great about the world and after a few hours driving, I need to stop for a coffee and a pee.

I drove and drove and eventually stopped at a rare sight in remote California: a Russian restaurant. I went in to check the place out and in front of me, on the wall, was a big painting of Abraham Maslow’s Hierarchy of Needs. Completely random!

The owner greeted me and her story was remarkable. She had a real interest in the Human Potential Movement and the Esalen Institute (which weirdly, I covered a few weeks ago!). After studying their work in depth, she moved to California. Then, after a trip to Burning Man, she had the epiphany to start a restaurant as a centre for personal transformation. Obviously…

The restaurant is on a ‘pay what you want basis’, it’s self-organised and runs workshops for personal growth. So I shared my thoughts and references around self-management and facilitation before attending an evening discussion group around instinct, emotion and intuition. What was supposed to be a quick pee, turned out to be several hours of great conversation.

LESSON #2: Planning limits potential.

I find it difficult to pull a lesson from this one, but I put it down to listening to the signs in front of us. Being free from self-imposed (and often artificial) structures of needing to be here or there; or doing this or doing that. I’m learning that openness to changing plans leaves room for magic to happen. The universe serves the right food at the right time it seems.

STORY #3: The person sitting next to you on your flight could work for the UN!

A few weeks ago I boarded my flight from Geneva to London after a great week at Alpselerator. I grabbed my seat and following a brilliant week, I must have had this kind of light smile about me. Any other day I might have been moody but that day, I was open.

Openness attracts open people and sitting next to me on the flight that day was a really nice British guy. He leaned over to introduce himself and we started chatting about our lives and got on really well. He was so curious about the kind of work I do, and where before I might have told him what I do, I found myself telling him why I do it.

I saw his eyes gradually open. When I eventually came up for air, he mentioned that he’d been looking for partners to help facilitate processes around collaboration and innovation. Another one of those coincidences.

LESSON #3: Openness opens doors. Why we didn’t ignore each other like on most other flights

I rarely speak to the person sat next to me on the flight, so I’m happy he did. In retrospect, I think the reason he did was simply because my body language and overall mood was open. He seems like a genuine guy and my biggest lesson from him is to be open to others, and take a little step to connect with the person next to me.

We’re still swapping emails a few weeks later and are now arranging a call in December about a possible collaboration. I haven’t shared his name here as I haven’t had the time to connect with him properly and ask permission. More to follow though I’m sure.

Making space for luck to emerge

I’ve made a lot of changes to the way I work, the most transformative one is moving away from planning everything. I used to work in tight timeslots, meetings, emails, deadlines with every minute of my week counted for. I wanted to ‘maximise’ my time as much as possible.

Now, I’m experimenting with a new way of living where I follow my gut and heart more. No clear outcome in mind, just a feeling that ’this is right’. Naturally following these ebbs and flows rather than planning leaves room for things to unfold and for luck and opportunity to arise.

I think that planning is a useful tool that we can overuse, often reducing the possibility of serendipity emerging. A huge opportunity cost I think! I can be quite controlling, so this is definitely a new way of operating for me.

Looking around and being curious

These experiences remind me of a book I read years ago called The Celestine Prophecy. The book shares 9 life insights (if you can put up with some average story-telling). The one I’m reminded of most is to listen to the coincidences and signs in front of us, guiding us forward.

I’m trying to listen and observe the world more and so far it seems to be allowing things to emerge that wouldn’t have otherwise.

Of course all of the above, could all be a quick series of lucky meetings but before, with my life bound by a diary, they wouldn’t have been possible. I would have never ended up in those situations and my likelihood of being influenced and guided by the world around me would have been very low.

So I’m going to keep testing and see where this continues to take me. Regardless, I feel lucky to have met some great people so early on my journey.

Peace.
JB

[Update: My latest coincidence]

Yesterday, I met a girl in a cafe in San Francisco who looked like she was struggling with a pen and pad. It turns out she’s trying to design a creativity workshop at The Exploratorium and has never done it before :) I’m going there tomorrow to help her design the workshop and then get a free afternoon at the Exploratorium, learning about Living Systems.