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Lisbon

This was a journey into Lisbon designed for leaders at a crossroads, navigating periods of loss and profound ambiguity.

Details

3 days | Up to 12 participants

As with every Sojourn, I interviewed and selected each participant.

The Choice of Lisbon

We chose Lisbon not for its beauty, though it has plenty, but because it offers a lived lesson in resilience.

On the morning of November 1, 1755—All Saints’ Day—an earthquake hit the city during mass. Churches crumbled. Fires broke out. A tsunami followed. In minutes, most of the city was gone in what seemed like divine judgment on Europe's wealthiest empire.

What makes Lisbon's response extraordinary is not that it rebuilt, but how it chose to rebuild. The Marquês de Pombal, appointed by King José I to oversee reconstruction, made the decisions to not restore the medieval labyrinth. Instead, Lisbon would be reimagined according to Enlightenment principles. The new city featured Europe's first earthquake-resistant construction, rational street grids, and standardized building heights—innovations born from catastrophe that influence urban planning worldwide.

But Lisbon didn’t erase the past. It kept its ruins—like the roofless Carmo Convent—on purpose. They wanted them to be reminders. Of fragility. Of change. Of what we carry forward.

That tension—between loss and imagination, ruin and reinvention—defines the city. And it mirrors the challenge many leaders face now: how to move forward without pretending nothing broke.

Highlights

Moving Through Disruption
At the Carmo Convent, deliberately left unrestored after the 1755 earthquake, we explored a question: When something falls apart, is it broken… or is it a break? And how do you know when it’s time to rebuild, or time to move on?

Organic Versus Strategic Growth
Alfama, the city’s oldest neighborhood, was never planned. Its streets twist. Its buildings lean. Yet it holds together. Walking through it, we explored what it means to grow not from strategy decks, but from close attention to place, people, and pattern over time.

The Usefulness of Melancholy
In a fado house, we encountered Portugal’s national music: songs of longing, loss, and endurance. Where most of business culture avoids melancholy, fado embraces it. We asked: What happens when organizations stop pretending everything’s fine? What strength might be found in naming what’s been lost, and choosing to continue anyway?

Photography by Tetiana Yarmolovych