The world is both infinite and intimate

You have to be looking for something in order to find something else

Mogambo is the kind of bar you don't stumble into. Tucked in Roppongi's neon and concrete, it requires some intention.

This past Saturday night its 8:30 PM and my wife and I are among the first to arrive. The bartender lets us know its still happy hour.

Ice cracks. Spirits pour.

The ritual of evening begins.

Three people settle next to us. The man to my left knows this place. You can tell by how he occupies space, how the bartender's greet him. A drink in… he turns.

"Greg?"

John from AlixPartners. Over a decade has dissolved between us.

Here's what I know about serendipity at forty: you have to be looking for something in order to find something else.

What am I looking for in Tokyo?

What are any of us looking for when we travel over 6,800 miles to celebrate another trip around the sun?

The Search That Precedes Discovery

I've been building software with AI for the past year. Each small act of creation a search for something I can't quite name.

We're all searching and always have been.

At AlixPartners, John and I had to search for solutions to complex business problems.

We were also searching for promotion, for recognition, for that next rung on a ladder we hadn't fully questioned the destination of.

Now, a decade later, here we are in Tokyo. He came to open the AlixPartners office and stayed.

Found love in his now wife at this very bar.

I came to mark four decades of existence, searching for... what? Perspective? Renewal? The feeling of being foreign to myself again?

The thing about serendipity—real serendipity, not the sanitized version we’re sold in movies—is that it requires both intention and surrender.

You have to be somewhere specific, doing something particular, open to interruption.

John and I spend the night excavating our past shared history. The people we knew. The evolution of the firm. And where they all are now.

We migrate to a lounge down the street. The conversation turns to AI, to how it will permeate everything, to my company's role in this strange new ecosystem.

But underneath the shop talk, something else is happening.

We're really talking about time. About choices. About the strange arithmetic of life.

How you can leave a place, become someone entirely different, and still be recognized instantly by someone who knew you then.

The thing they don't teach you in consulting or Tech or any of our carefully optimized worlds: the best things happen in the spaces between intentions. You optimize for one outcome and get another.

You build a feature no one uses that leads to discovering what they actually need.

You sit down at a bar in Tokyo proper (a city of 14 million people) and the stranger next to you isn't a stranger at all.

I’ve written about how we need to be "productively wrong”.

Here’s what I think now. It's not just about products or code. It's about life itself. The glitch in my pattern was thinking Tokyo would give me space and perhaps some solitude for reflection.

Instead, it gave me John, gave me connection, gave me a mirror to see how far I've traveled while somehow staying exactly myself.

An anchor and a sail

Here's what forty years teaches you: your reputation is both an anchor and a sail.

It travels ahead of you into rooms you haven't entered yet. It sits in bars you haven't discovered, waiting in the memory of people you haven't seen in a decade.

John remembers me as someone specific. I remember him as confident, connected, someone who probably understood a few things I didn’t.

Tokyo is massive. There are 37 million people in the greater metropolitan area. The odds of sitting next to someone you know are essentially zero. But the world of people like us—consultants turned tech workers, expats and wanderers, seekers of the next thing—is surprisingly small.

We create these probability fields around ourselves. Frequent the kinds of places our kind frequent. Move in orbits that intersect more often than pure chance would suggest.

This is the paradox of modern life: the world is simultaneously too big to comprehend and too small to hide in. AI, I think, will make it smaller still.

But for now, for this night, it's just flesh and blood and memory and alcohol creating this temporary bridge across time.

At forty, I realize the search itself is the finding. We look for success and find complexity. We look for meaning and find moments like this one, unexpected and perfect and already slipping away.

Another life. That's what it feels like. But also this life. The same continuous thread, just woven through different scenes.

Whatever happens to you has been waiting to happen since the beginning of time. The twining strands of fate wove both of them together: your own existence and the things that happen to you. — X.5

The Permission to Be Found

Here IS what else I didn't expect about serendipity: it requires permission. Not just to find, but to be found.

When John recognized me, I could have deflected. Could have been polite but distant.

Instead I let myself be known. Let the past and present collapse into each other. Let John see both who I was and who I've become, and didn't try to reconcile the contradictions.

This is maybe the greatest gift of serendipity: it reminds us that we're continuous with our past selves, even as we're discontinuous.

But tonight we're suspended between who we were and who we're becoming. Tonight, in a bar encounter that shouldn't exist, having a conversation that couldn't have been planned, we're evidence that life resists optimization.

Forty years old, 6,800 miles from home, I find myself thinking: maybe we're all just searching for witnesses. People who can say, "Yes, you were there. Yes, that happened. Yes, you've changed, and yes, you're still you."

Maybe that's what serendipity really is.

Not the thing you find when you're looking for something else but the moment when what you're actually searching for reveals itself in the finding.

Its late and we decide to close out our tab. Last train has already passed. John and I exchange numbers. We say our goodbyes.

As time folded in on itself for that one night in Tokyo it showed me something true:

• We're never as lost as we think we are.

• Someone, somewhere, remembers our name.

• The world is both infinite and intimate.

And sometimes, just sometimes, the thing you were looking for was looking for you too.