Stories from the Road

I kept a note on my phone for a while called "stories from the road": brief records of conversations and encounters from business and personal travel that seemed worth remembering. Not the landmarks or the itineraries. The specific moments with specific people that did not fit any planned agenda.

Here are some of them.

The taxi driver in Dubai

Three hours before a significant pitch meeting. The taxi from my hotel to the client's office in DIFC. My driver was originally from Kerala, had been in Dubai for eleven years, sending money home each month, visiting twice a year.

He asked what I did. I explained: executive search, placing senior leaders for companies. He was quiet for a moment, then asked: "How do you know if someone is honest before you hire them?"

I gave him the answer I give clients: references, behavioral interviewing, looking for consistency between what people say and what their history shows. He listened carefully, then said: "In my village, before someone does business with someone, they watch them for a season. They watch how they treat their family, how they treat people who need help, how they behave when nothing is at stake. Only then they decide."

I thought about that conversation during the pitch. And several times since.

The hotel in Almaty

Kazakhstan in March. The hotel was Soviet-era, refurbished but not quite able to shake the original bones. The concierge had been working there since before independence, had watched the same building be called different things under different systems.

I asked him what he thought of Almaty, whether he thought it had changed for better or worse. He considered this seriously. "Before: more order. You knew the rules and if you followed them, you were okay. Now: more freedom. But freedom means you can also fail. More people doing better. Also more people not okay."

He was describing a development transition in the terms of someone who had lived through it, rather than the terms of an economics paper. The tradeoff he was describing, legibility and security versus possibility and risk, is the core tension in almost every development choice, and he had put it more clearly than most of the literature.

The flight to Singapore

Seated next to a woman returning from a difficult meeting in Mumbai where a company she had invested in had just told her they were shutting down. She was not performing distress: she was just sitting with it, visibly, and something about the contained quality of her processing made the story come out naturally over the course of the flight.

She had invested early in the company. It had not worked. She was thinking out loud about what she had missed in her evaluation: what signals had been there that she had not adequately weighted.

What struck me was the quality of the retrospective. No defensiveness, no blaming the founders, no reframing the failure as due to circumstances rather than judgment. Just precise identification of the specific errors: I weighted their track record too heavily, I did not spend enough time understanding the competitive dynamics in the specific vertical, I liked the founders personally and it colored my analysis.

The discipline of that honest post-mortem, in the immediate wake of the thing, was genuinely impressive. I asked if she always processed failures this way. She said: "I try to. It's the only thing I know how to do that actually improves the next one."

What these have in common

The encounters worth keeping from years of travel almost always involve someone thinking carefully and honestly about something real. Not performing sophistication or signaling expertise. Just engaged with a genuine question in a way that produces clarity.

It happens in taxis and hotel lobbies and middle seats on long-haul flights. It does not happen in conference rooms very often, which I suspect is because the conference room format invites performance rather than honest engagement.

The road has taught me to prefer the conversation that starts unexpectedly over the one that was scheduled. The accidental ones tell you more.

See also: When Generosity Is the Default, Langkawi: The Day Everything Looked Perfect, Lessons from Airports