How to Design Remote Serendipity

Pete Sena
7 min readMar 18, 2021

“Defining moments can be consciously created. You can be the architect of moments that matter.” ~ Chip Heath, from The Power of Moments

As a leader who has run a very collaborative, face-to-face agency for 14 years, I vividly remember the defining moment of 2020, for my business at least. It was when we decided to temporarily close DISTRICT, the innovative coworking space that’s home to Digital Surgeons, among other creative and entrepreneurial companies.

That day, now more than a year ago, feels burned into my brain. And my heart, truthfully. It was the moment that transformed us into a remote company literally overnight. (Happened to the best of us…)

So what does one do when faced with an unprecedented challenge?

Honestly… at first, I panicked.

Then I saw it as an opportunity to design a new way forward. We were already using so many digital collaborative tools that flipping into all virtual communication, whether synchronous or asynchronous, went pretty smoothly.

But then life settled into a predictable pattern. After a while, it started taking on a Groundhog Day-esque flavor. My team and I were getting things done, but I couldn’t help notice how much was lost without being together in person. Commiserating about Zoom fatigue is its own special kind of bonding, but it certainly doesn’t help with morale.

Now that vaccines are starting to become available to more people, we’re all hoping that life will go back to “normal” in the next few months. Many of our teammates have been sharing how much they miss the in-office environment. Others have commented on how much they love the remote workflow. I believe part of the new normal is keeping a fair amount of flexibility in our schedules and embracing distance and remote work, at least some of the time, as part of our culture.

So, for business leaders who care about having a close-knit crew (I know I do), the paradoxical question is, how do we plan for serendipity? Those moments that crop up organically in person are harder to come by without physical proximity.

This post is as much a question as it is a series of experiments and answers — many of which I still have no clue about.

Pete Sena

I help founder-led businesses design demand 📈 ⚡️3X Founder / Operator / Investor | Ready to design demand for your brand? 👇