The Stuff You Don’t Plan For Is Usually the Point

You can schedule the trip. You can’t schedule what matters.

We had a full itinerary in Africa. Safaris, dinners, wine country, the whole thing. It was well done, structured, and intentional.

And still—the stuff that stuck with me wasn’t on the schedule.

It never is.

The conversation you didn’t expect

We had a driver taking us to the airport. Probably mid-20s. Normal ride, nothing special.

Then somehow we get into marriage.

He tells us he can’t afford it.

Not because of the wedding.

Because of cows.

Five cows to get married. Eight if she’s smart.

You sit there for a second and think… alright, this is a completely different operating system.

And then he says he wants to move to the U.S. because “you get a wife for free.”

That’s the kind of moment you don’t get at a conference.

The parts no one presents

There was a woman working at the lodge named Gift. Someone asked her why that was her name.

Turns out she was the surprise fifth child. That was it. That was the story.

Simple. Honest. Memorable.

What’s funny is even the manager didn’t know her story. It took someone asking.

That’s usually how it works—those stories are there, but they don’t surface unless someone is curious enough to go find them.

You can’t manufacture perspective

You can go to all the right places, stay in the right hotels, do the right experiences.

But perspective doesn’t come from the plan.

It comes from noticing something slightly off… and leaning into it.

A dead tree that actually serves a purpose.

A culture that operates on completely different rules.

A conversation that wasn’t supposed to happen.

Why this matters (even in business)

I think people try to engineer growth the same way they plan trips.

Structured. Efficient. Optimized.

But the real insight—the kind that actually changes how you think—usually comes from the unplanned parts.

The side conversations.

The random observations.

The moments that don’t feel productive at the time.

Final thought

If everything about what you’re doing feels controlled, predictable, and polished…

You’re probably missing the point.

The value is usually sitting just outside the plan.