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The Productive Person’s Guide to Welcoming Serendipity

Sep 14, 2015 5 min readOpen

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

Those two novels capture a fascinating concept: Serendipity. I love how the characters embark on journeys where they learn a lot by trying to find their own path, through many chance encounters and learnings.

Outside of the fantasy world and back in our own reality ,  I got to wondering what these concepts look like in my own life. We all want to maximize our productivity, and many of us try tactics like to-do lists, predictable routines and repeatable processes.

But where does that leave serendipity? In the midst of optimizing our efficiency, can we also create time for chance encounters, adventures and wanderings?

How can we focus on productivity, and still welcome serendipity?

welcoming serendipity

Productivity through routine

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

One of the best tips I have found to keep everything in order is to embrace a routine (the Buffer Social Blog did a great story on various types of routines if you’d like to create your own).

As a remote worker, this tactic helps me stay organized and give the best experience possible to my colleagues and our users. It also saves me from the other extreme of remote working—working around the clock.

I travel a lot—most of the time by myself—and 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.

Benjamin Franklin's to-do list
Benjamin Franklin’s to-do list

It feels that I know quite well how I work best, but 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?

Conforming to a routine certainly is great for my productivity, yet allowing for serendipity helps me recharge my creative batteries by meeting inspiring people and having unique experiences. Can they work together?

Welcoming serendipity in work and play

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

I have never been very good on “letting go” so instead I often consciously make time to welcome serendipity — for instance, by hitchhiking through Poland to sailing across the Atlantic.

The yacht Dory
The Dory, the yacht I sailed across the Atlantic in.

In 2013, I quit my job and went traveling for one year with very little planning. It was such a great experience, and 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. Serendipity helps me to embrace what is outside my comfort zone and allow for what I cannot predict nor control.

And at the end, I was very happy to get back to a more settled routine that freed me from some of the “analysis paralysis” I had felt—a possible consequence of serendipity  that makes it harder to make decisions.

As a remote worker, serendipity in the workplace mostly happens online, which is a different setup than a face-to-face conversation.

Since I don’t see my colleagues very often, 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.

And twice a year, the entire Buffer team flies to a given city for 10 days in order to meet up, work and play together. It has been amazing to see how much enjoyment we have every time we come together, and how many ideas come from us all being in the same space!

Balancing serendipity and 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 in a conversation, traveling to a new place, simply saying “yes” when you might have been defaulting to “no” almost always results in fun adventures!

Here’s a neat look at some of the conditions for serendipity:

conditions for serendipty

It feels to me that introverts and extroverts might allow for serendipity differently.

It almost seems that my energy level is an indicator of whether I’m up for it. When I feel like I need some “me” time, I’m not likely to allow for it and will rather default to my routine. When I feel like connecting or mingling, I’m up for it!

If I were to say “yes” to everything ,  I think it might be a lot trickier to keep making progress on all my commitments. I love Derek Sivers’ article “No more yes. It’s either HELL YEAH! or no.” for how it clarifies this point:

“When deciding whether to commit to something, if I feel anything less than, ‘Wow! That would be amazing! Absolutely! Hell yeah!’ – then my answer is no.

When you say no to most things, you leave room in your life to really throw yourself completely into that rare thing that makes you say ‘HELL YEAH!’ “

My sense is that you can find serendipity both by yourself (journaling, taking pictures, meditating) and with others (planning fun encounters, socializing), no matter your level of introversion or extroversion.

Over to you!

I recently attended the DNX Conference in Berlin, where I was lucky to chat about serendipity with many nomads. I shared that my best learning so far has been to stay open to new experiences, shy away from judgment as much as possible and—when in doubt—save up my resources by 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.

routine vs serendipty

Those have been my learnings so far, but what do you think? Do you have a productivity routine? Do you have methods to make room for serendipity in your life? It would be amazing to hear your thoughts in the comments.

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