The Unexpected Paths That Shape the Way We Lead
The very few truly meaningful moments in my career never began with a strategy, a plan, or an acknowledged objective. They began with a conversation I never expected to have. A challenge I had come to see myself facing, but didn’t actually intend to take on or plan on solving. An opportunity that wasn’t in the stars or the plan. Simply the natural end of a work project or an era in my professional life. A failure, even.
Every time, it was something that changed everything. Unexpected. Some can say it was because I didn’t truly know what I wanted so as to pursue and attain the serendipitous result as an authentic objective or milestone; others think I was rather led by serendipity. It could be, either way. But the fact is, more than once, I’ve found myself standing at a crossroads I hadn’t anticipated — and making a decision that I would have dismissed having the opportunity to make.
Lately, I’ve started to reflect on leadership and how people do it: people around me, people I look up to, people I work with. What I’ve come to grasp so far is common sense, really: it’s not just about having a vision or executing a plan — even if both definitely matter. It’s also about being willing to pause, notice, and respond to what’s happening around you.
I’ve come to believe in the hushed power of serendipity.
What it is to lead by serendipity
Leading by serendipity isn’t about leaving things to chance. It’s about acknowledging and embracing that not everything important can, or for that matter, should be predicted, foreseen, or controlled, and that everything important can and maybe should always graciously unexpectedly sweep you off your feet.
What I believe it means? A couple of things, to begin with: trust intuition and expect surprise. Follow curiosity, and not just protocol. Pay attention to what connects and coalesces your team. Say yes to something exciting before having fully dissected it to the smallest of objective atoms of knowledge. Trust a gut feeling, even if the data crunched in disagreement. Listen and allow new people, projects, and paths to redirect your thinking.
Some of the most look-up-to-worth leaders I are those who stay present, those who stay open to people, to changes, to possibilities, those who stay mindful.
Serendipity cannot be forced, nor actively expected, or else it would defeat its very purpose. But I reckon space can be made for it. The very first step? Know where it comes from and then see whether it has already shaped a turning point in your leadership style.
An unexpected fortunate discovery, the term serendipity was coined by writer, historian and politician Horace Walpole in 1754, referencing the Persian fairy tale The Three Princes of Serendip, where the protagonists make canny discoveries of things they were not looking for. Although it has been long talked and addressed in science and academic literature, I believe it got its worldwide recognition with the lovely romance movie from a lifetime ago, Serendipity starring Kate Beckinsale and John Cusack.
Call it active luck by pairing equal parts of pure chance and human action, say chance meets conscious action, but either way, the crucial part is played by the person – the leader – who can see and act upon unexpected opportunities, and then look back for the a-ha-serendipitous moment.
Has serendipity ever shaped a turning point in your career or leadership path?
I’d love to hear your story — feel free to share in the comments below or message me directly.
Nefelibata 
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