Harvesting Meaning: Why Most Gatherings Feel Empty (and How to Fix Them)

Have you ever been part of a gathering where everyone’s there… but nothing’s really happening?

You look around the room — or the Zoom — and think, “Why are we even here?”

Now imagine that scene — but in Italy.

With nine friends.

And no olives.

Every year, for the last eight, my friends and I head to Le Marche for what we call The Olive Harvest.

A week of picking olives, eating, laughing, pretending we’re wholesome Italian farmers.

It’s our ritual — the kind that fills your camera roll and your heart.

Except this year, there was one tiny problem:

No olives.

None. Zero. Niente.

Our friend knew it, but said, “Let’s go anyway — we’ll still have fun!”

So we did.

Day one: we walked around squinting at trees, hoping to find even one olive.

Day two: baskets got replaced with bottles — wine bottles.

By day three, we’d run out of topics, snacks, and the energy to pretend we were having fun.

Nine people surrounded by Italian beauty… and nothing meaningful to do together.

It felt like a corporate off-site — just with better food.

By the end of the week, we were united on one thing:

“If there are no olives next year, we’re not coming back.”

The Moment of Realization

On the flight home, I stared out the window and wondered,

How did something that used to feel so special turn so empty?

That’s when I remembered a Japanese phrase I learned years ago in facilitation training:

Ichi-go Ichi-e — “One time, one meeting.”

It’s a reminder that every time people come together — whether in a boardroom, a workshop, or an olive grove — that moment will never happen again in exactly the same way.

It’s an invitation to design gatherings with intention,

because meaning doesn’t appear by accident — someone has to create it.

Ritual vs. Intention

After facilitating hundreds of meetings, I’ve learned this:

If a gathering doesn’t have a clear why, it quietly turns into whatever.

You know the type — the daily check-in where half the group is on mute, the other half multitasking, and everyone leaves wondering what the point was.

We mistake routine for purpose.

We meet simply because we always have.

That’s exactly what happened in Italy.

Our olive harvest had become a ritual on autopilot.

We went because we always went.

No one asked what we wanted from being together this year.

If we’d paused to ask, “What could make this year special?”

maybe we’d have created something new —

a cooking week, exploring Le Marche, even a small project together.

Instead, we relied on tradition — and ended up harvesting boredom.

The Business Parallel

Sound familiar?

It should.

Most teams run their calendars the same way.

We schedule meetings because they’ve always been there.

We host town halls because it’s Q3.

We run off-sites to “re-energize” — and then wonder why everyone returns to business as usual.

Meaningful collaboration doesn’t happen by adding more gatherings.

It happens when someone stops and asks,

“Why are we meeting at all?”

At work, as in life, intention is the olive that gives the harvest meaning.

Without it, you just have people standing around beautiful trees, pretending they’re productive.

From Habit to Design

So before your next meeting, workshop, or team off-site, pause and ask:

• What makes this gathering worth people’s time and energy?

• What could make this moment — not just the agenda — matter?

• How will people feel different walking out than when they walked in?

Because every gathering, whether in a vineyard or a virtual room, is a one-time event.

Even if it happens again next week, the people, the energy, the context — they’ll never be the same.

Design for that.

Anchor your rituals in why, not just when.

The Takeaway

Ichi-go Ichi-e isn’t a poetic ideal — it’s a practical mindset.

It’s how you turn autopilot meetings into meaningful moments.

It’s how you build connection that lasts beyond the calendar invite.

Because every gathering is once in a lifetime.

The only question is — will it matter?