Instead of Networking, Build a Serendipity Engine

Daniel Stillman
6 min readApr 26, 2022


What is a Serendipity Engine?

It’s hard to know what moments are going to be the ones that really matter in life, since there’s no movie music playing in the background to cue you on the portent each moment may hold.

I write this essay, for myself, and maybe for you, too — if you, like me, feel exhausted from time to time by networking and “getting out there”.

Networking sounds like a lot of work.

I mean, it’s right there in the word! Network

Being open to serendipity is a radically different approach to building a network.

Any one conversation can lead to so much more. We can look at each moment as a transaction, or a moment in a potentially infinite story — an opportunity to find out what is possible, if we meet that moment with curiosity.

Having more moments of potential serendipity and unexpected transformation can help you create a life you love, build a better network and find amazing opportunities…without it seeming like so much work.

My coach and I call this way of living having a “serendipity engine” — consistently creating moments of potential connection and designing a cadence of connection in your life that can lead to unexpected, deeper connections if you’re open to them.

Do you have a serendipity engine? I’d love to hear about it — you can share it on LinkedIn on this thread.

One of my serendipity engines is the Facilitation Masterclass I host— a 12-week transformational program that evolved from a one-day workshop back in 2018.

My other serendipity engine? The Conversation Factory Insiders group and the Facilitation Friday sessions I host with that group.

I’m going to tell you a personal story, show you a picture that sparks joy for me…and then give you seven tips for building a serendipity engine.


In 2017 I was on the road a lot, in lots of time zones. I was often tired, and I often had the sniffles from airplane air.

Usually, I had just enough energy to do the workshops I was hired to do, and then sleep. I wanted more diversity in the work I was doing, but I didn’t know how to create it.

One night, I got a WhatsApp message from my friend Richard who asked me to connect with a friend of his: someone who was, at the time, leading Google’s Sprint community, which I knew pretty much nothing about.

I fit the call with Richard’s friend into a late night (for me) in the wrong time zone for my body. To be honest, I wasn’t really sure what the call was about…and I certainly didn’t know what would come of it.

It was through that conversation that I got invited to the first Google Sprint Conference (SprintCon for short) at their San Francisco offices.

It was an amazing event. I wound up meeting rockstars and powerhouses in the design innovation world — some of who went on to become new friends and collaborators, but not for another year or more.

I also learned that Google’s San Francisco office made the most amazing chocolate chip cookies. True story.

In 2017, I was mainly an attendee. However, I did get to help run one session at the last minute through *another* conversation…and because of that session, the following year, I was invited to offer a full-day pre-conference workshop leading into the 2018 SprintCon.

In conversation with the organizers, and to differentiate my session from an introductory Sprint Facilitation session being offered, we agreed to call my one-day workshop an Advanced Facilitation Masterclass…which was so audacious of a title for a one-day workshop that some deeply talented folks came to the session. That’s where the “workshop selfie” below happened…a hinge point in my Serendipity Engine.

I love taking workshop selfies. Back when we met in-person, I would struggle, hilariously, to get all the participants into one shot.

(recently, I learned on Ted Lasso that these kinds of pics should be called “ussies” since they are a shot of “us” not “just myself)

That session led to so much more. I wound up offering a version of that workshop to organizations all over the world. Ross Chapman, grinning in the back, hosted me to run a similar workshop in London a year later.

I met amazing people in that session, like Christen Penny, one of my favorite coaching clients ever (who was also on a recent podcast) and Tomomi Sasaki who I admire greatly and who came on my podcast to drop some wisdom earlier this year.

One conversation in 2017 led to some of the most personally and professionally rewarding experiences of my last FIVE years. When I think back to how tired I was on that late night, seemingly random call with a friend of a friend, and how I didn’t really understand who I was talking to, what a Google Sprint was, or what would come of it all, it makes me wonder — have there been other hinge points since then, that I don’t understand the impact of, just yet?


The truth is we never know when the hinge points in our lives are until much, much later.

I didn’t know the call would result in the conference, or that there would be another invitation to the next one…or that that workshop selfie would make me smile with gratitude in 2021.

And the *really* funny thing?


I think Richard and I had only connected over a few phone calls at that point, over the course of a few years. We hadn’t even met in person!

I got connected to Richard in 2015 when my life was falling apart.

I had just been ousted from a company I had started three years earlier…and had no idea what to do with myself: so I reached out to some trusted friends who eventually connected the two of us.

The time from mid-2015 to the SprintCon in 2017 was a turbulent, complex and challenging phase in my life. I wish I had known that a corner was coming…but I didn’t.

I hope this essay helps you attune your antennae to serendipity, to scan the horizon for more opportunities to create surprise, and to meet those moments with curiosity, wondering what might unfold.


  1. Say yes. Say yes to anything that lights you up, seems interesting, or sparks your curiosity.
  2. Say no. Say no to everything that doesn’t meet the criterion in #1. It will leave you more space for things that do.
  3. Show up with curiosity and enthusiasm. Being your best self means that people get to see the real you. If they like it, hooray! If they don’t…even bigger hooray! A clear no is great information that helps you move on to the next
  4. Connect with people you like one-on-one. Take time to get to know them. And then ask for help and connections. People love to help — don’t you?
  5. Find and leverage communities. One-to-one conversations are awesome, but many-to-many conversations (like book clubs, meetups, conferences and the like) provide connection at scale, and increate your serendipity.
  6. Be the host. Don’t wait for #5…make your own opportunities for cross-pollination and many-to-many conversations.
  7. Repeat. Say yes to conversations that come out of 1–6. The more times you get to #7, the more your serendipity engine will become a flywheel.



Daniel Stillman

Executive coach. Host of Often riding bikes to the ocean.