The Productive Person’s Guide to Making Moments of Serendipity

Serendipity |ˌserənˈdipitē|

The occurrence and development of events by chance in a happy or beneficial way.

I recently re-read two books that had a big impact on my upbringing — The Alchemist and The Little Prince— and a thought hit me:

Pen-and-Ink drawing by Antoiine de Saint-Exupéry (Christie’s -NYC - 2009)

Those two novels capture a fascinating concept: Serendipity.

I love how characters embark into journeys where they learn a lot by trying to find their own path, through many encounters and learnings.

When we step outside of those fantasy world, and settle back into our own reality — I got to wonder:

How can we be productive, and still welcome serendipity?

A Look At Productivity

Today, I work full time at Buffer and I run Remotive on my spare time — things have been quite busy! I get a lot of enjoyment and energy from running multiple projects at once, I even dedicated my main project to productivity

One of the best I found on productivity is to embrace a routine, the Buffer Blog did a great write up on various types of Routines.

As a remote worker, it feels super important for me to give the best experience possible to my colleagues and our users. So far, this has gone through getting organized.

It also saves me from the other extreme of Remote Working, that is working around the clock.

Ben Franklin’s routine, circa 1700's

I travel a lot, most of the time by myself, yet I find myself replicating a pretty similar routine in any place I visit — a good early morning session, lighter tasks before lunch, long lunch, nap and break before I get back to it mid-afternoon until evening.

It feels that I know quite well how I work best, there’s still a lingering question here:

If I conform to a given routine, and become super productive, is there any space left for serendipity?

Relaxing in India (Palolem Beach)

Welcoming Serendipity

Conforming to a routine certainly is great for my productivity, yet allowing for serendipity helps me recharge my creative batteries by meeting many inspiring people. It is also associated for me to embracing what is outside my comfort zone, to allow for what I cannot predict nor control:

I love going on adventures, and I have been lucky to go on quite a few, ranging from hitchhiking through Poland to sailing across the atlantic.

Reflecting back on everything I’ve experienced so far, spontaneous decisions and random encounters through my life shaped me into the person I am today.

I have never been very good on “letting go”, so far I often consciously make time to welcome Serendipity — for instance, by going for a sailing trip. Sailing trips are always very eventful!

Sailing Yacht” Dory” before our 21-day sailing trip — Picture by Jon

As a remote worker, serendipity at work place mostly happens online, which is a different setup that a face to face conversation.

To make up for it, we still foster interaction by going to retreats:

Twice a year, the entire Buffer team flies to a given city for 10 days in order to meet — it has been amazing to see how much enjoyment and ideas we have overtime we come together!

Since I don’t see my colleagues very often, so I find it critical to join a co-working space, go to events and attend conferences to keep connecting with others and be inspired by them.

Balancing Serendipity & Productivity

To me, serendipity is embracing novelty.

It’s a state I deeply enjoy, although it can be uncomfortable to step outside my comfort zone. Engaging a conversation, traveling to a new place, simply saying “yes” when you might have been defaulting to “no” almost results in fun adventures!

Also, it would feel to me that Introverts and Extroverts might allow Serendipity differently.

I personally feel like a mix of both — when I feel like I need some “me” time, I’m not likely to allow for it and will rather default to my routine. Yet when I feel like connecting or mingling, I’m up for it!

My sense is that you can find Serendipity both by yourself (journaling, taking pictures, meditating…) and with others (making fun encounters, socializing…).

Enjoying some “me” time in Buenos Aires

It would almost feel that my energy level is an indicator of whether I’m up for it.

On the flip side, if I was to say “yes” to everything — I think it might be a lot trickier to keep making good progress on all my current commitment. I love Derek Sivers’ article titled “No more yes. It’s either HELL YEAH! or no.”

In 2013, I had saved up some money, I quit my job and went traveling for one year with very little planning — it was such a great experience, I managed to say “yes” to so many things, including a pirañas fishing attempt somewhere in the Amazon forest!

From that year, I learned immensely and was still very happy to get back to a more settled routine that freed me from “analysis paralysis”, a possible consequence of serendipity — making it harder to make decisions.

I recently attended the DNX Conference in Berlin, where I was lucky to chat about Serendipity with many nomads.

My best learning so far has been to stay open to new experiences, try to shy away from judgment as much as possible and — when in doubt — resourcing myself through going back to a routine for a bit, wherever I am.

Following a routine feels like an anchor point for productivity, and serendipity is best found when I venture out of this anchor point!

Those have been my learning so far, it would be amazing to hear your thoughts in the comments :)

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Founder at @remotiveio | Prev. Director of Operations at @Buffer

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Rodolphe Dutel

Rodolphe Dutel

Founder at @remotiveio | Prev. Director of Operations at @Buffer