Upon Arrival: Systematising Serendipity
Unlock faster, smarter commercial outcomes by moving beyond inner circles.
Until recently, reaching beyond our inner circles and familiar networks, and turning them into commercial outcomes, took time, effort and, often, a degree of chance. That’s shifting. And for those building across borders, it matters.
In This Is Strategy: Make Better Plans, Seth Godin writes:
In international business, broader circles are strategic.
Expanding who we include unlocks insight, access, and momentum; these are often missed when blind spots and biases go unchecked. This matters as global shifts redraw where business is done, how advantage is built, and what it now takes to win.
Systematising Serendipity
New tools are making people-to-people exploration more deliberate. In a world of smart prompts and curated matches, the focus shifts from meeting more or official people to meeting the right ones.
Startups like Clay, Lunchclub, and Upstream are building tools to systematise serendipity - finding second-degree connections, curating introductions, and suggesting outreach based on location, timing, and shared interests.
Clay uses AI to scan your network and prompt timely connections. Lunchclub matches you with people just outside your usual circles. Upstream facilitates warm introductions through interest-based groups. Meanwhile, newer platforms like Boardy are layering in verification, relevance scoring, and travel-aware recommendations.
Soon, instead of arriving in a new city hoping for the right conversation, you’ll be nudged toward it.
You might land in Nairobi and be shown three mutual connections relevant to your focus, with pre-drafted outreach messages tailored to local context. Or receive a prompt to meet a local founder speaking at a nearby event, based on calendar integration, interest signals, and strategic fit.
Arriving, Today
Today, we arrive in a new city with a frame - of reference, assumptions, and contacts. From the arrivals hall onwards, we can follow a plan or expand our perspective.
This edition of Crossing Borders explores what shifts when we expand our lens and step beyond the familiar, whether through second-degree connections, serendipitous signals, or reframing what we notice on arrival.
Although set in a foreign airport, the insight applies anywhere: often, the most valuable perspectives come from those just outside our usual circles.
An UNfavourable Arrival
The moment I decided to leave my job at the United Nations came in the diplomats’ line at Entebbe Airport in Kampala. With my pale blue UN Laissez-Passer passport in hand, I joined a queue of around twenty others holding the same. We were likely all there for international development work albeit from different agencies, different acronyms, yet the same line.
I had arrived with a full itinerary. A week of export strategy workshops, multi-sector facilitation, and technical sessions with ministry staff. Yet as I stood there, it dawned on me that I didn’t know who any of these people were. I didn’t know what parts of the puzzle they were managing. I had no sense of how our pieces were meant to connect, or even if they did.
It felt like the optics of being important, as an international diplomat, didn’t match the outcomes, which were of vital importance to the country’s citizens and the economy.
In that line of work, it seemed as if weak networks were allowed and silos were normalised. However, increasingly in global business, that results in costly blind spots.
Now, advantage sits with those who can map the system, not just manage their slice of it.
That mapping can begin at arrivals.
Serendipity Theory, as outlined by Christian Busch in The Serendipity Mindset, describes how leaders who cultivate curiosity, preparedness, and openness are more likely to convert unexpected encounters into strategic breakthroughs. Serendipity isn’t passive. It’s a mindset, what Busch calls “smart luck.” It’s about seeing triggers, acting on them, and creating conditions where a passing conversation or casual introduction becomes a source of insight.
Imagine travelling to a new city tomorrow. How would you navigate the Arrivals Hall? Here are two ways to approach it; by default or by design.
Option 1: Default to the Familiar
You follow the signs, from immigration, to baggage, to car service, with the confidence of someone who’s done this before. You smile politely at fellow travellers but stay focused on your itinerary. You’ve reviewed the briefing pack, your meetings are locked in, and a driver waits holding your name just beyond the barrier.
It’s the default approach for many experienced leaders. It works. It’s how international business trips have been structured for decades: move seamlessly from airport to meeting room with as little disruption as possible. Yet in doing so, the experience becomes tightly managed and carefully contained. It’s predictable and also removed from the nuance and shifts of what’s unfolding in-market.
Upside: Efficient and polished, it allows you to stay in control and on schedule.
Downside: You risk seeing only what’s already known, missing the nuance, energy, and edge that lie just beyond the formal programme.
Option 2: Design for Discovery
You take the same flight, clear the same gates, and exit the same terminal yet your approach is more deliberate. You see the journey beyond being a transit, rather as a window for gaining early signals and shaping smarter context before the formal meetings begin.
You start with a conversation in the immigration queue. The person beside you turns out to work in a complementary sector and is staying at your hotel. You share a car. Over the drive, you hear where local capital is moving, or how policy is shifting in ways that haven’t made the briefings yet.
At the baggage carousel, rather than asking for directions, you ask a staff member where business people tend to meet before work. She mentions a nearby café, one you hadn’t flagged. You reshuffle your first morning. What you learn there informs the rest of your trip.
Or, anticipating the arrival, you reach out to a second-degree connection on LinkedIn before departure. You’ve never met, but there’s mutual trust through a shared contact. They agree to a short coffee between meetings. In thirty minutes, you gain insight into current conversations shaping the business climate and leave with a thread that proves far more relevant than expected.
Upside: You create space for new information, context from those already immersed in the market, and the kind of unexpected relevance that strengthens decisions and connections.
Downside: It takes more intention. You have to ask, listen, and be ready to adjust, which can feel harder with jet lag.
Where We Land Doesn’t Determine How Far We Go
Where we land is fixed; what we see and unlock is not.
In fast-moving markets, the edge goes to those who pause, observe, and act on signals others miss.
Leaders who stay open, curious, and prepared are more likely to turn these moments into meaningful insight, what Christian Busch calls “serendipity that’s earned.”
Increasingly, the most valuable information isn’t in the briefing deck. It’s in the coffee queue. The comment in transit. The conversation we nearly skipped.
The world is shifting. How we see, act, and show up can shift with it.
Because when we see the bigger picture, we can play a bigger game.
What’s the unplanned conversation that could unlock what matters most in an unfamiliar, foreign setting?
Further Reading:
This Is Strategy: Make Better Plans, Seth Godin. Available at: https://seths.blog/tis/
The Serendipity Mindset: The Art and Science of Creating Good Luck, Christian Busch. Available at: https://theserendipitymindset.com/books/
The Twilight of US Global Influence, Project Syndicate, On Point, June 2025. Available at: www.project-syndicate.org/onpoint/the-twilight-of-us-global-influence
Cross Borders & Break Down Barriers
As leaders and markets contract, is aiming bigger and going global still viable?
Several key world leaders are set to rule for the next four years - this contraction may well be the status quo we’re working within.
Yet for some leaders, entrepreneurs, and businesses, there’s a pull to go beyond this new normal.
Florentine diplomat and author Niccolò Machiavelli captured this sentiment:
“I’m not interested in preserving the status quo; I want to overthrow it.”
And for good reason. Because while political and economic barriers rise, other shifts are reshaping global business opportunities.
Breaking Out of the Small Pond
Some leaders are happy being a big fish in a small pond. Others yearn for a bigger ocean to swim in.
There’s a group of established and emerging leaders who see beyond their immediate horizons. They want to take what works in their domestic market or region and expand it globally. What’s their mission? To earn foreign revenue, diversify markets, de-risk their business model, and amplify their impact on a global scale.
Yet bigger oceans aren’t without their threats. Larger competitors exist, and while bigger opportunities await, so do bigger challenges.