The Unexpected Leadership Magic of Unpurposed Time

I am writing this from a hammock at dawn, waiting quietly for farm chores to start. Yes, farm chores—because apparently, relaxation for me now includes pitchforks and hay bales. Who knew?

Last year, amid my usual whirlwind of work travel, I decided to dedicate one-on-one trips with each of my kids. When your job has you away as often as mine does, uninterrupted time feels like a luxury you can’t afford to waste.

This time around, my youngest and I landed at the Ocoee Riverside Farm.

A magical place, truly. But here’s the real magic I discovered:

True connection rarely happens when connection is the goal. It thrives instead in the "unpurposed" moments—the spaces in-between.

Think about taking your kiddo out for a special dinner (which you absolutely should do). Everyone arrives ready for meaningful dialogue. They’ve got their polished anecdotes ready, hoping you pick up on their highlight reel without explicitly asking. It's lovely, sure, but sometimes it feels just a little too orchestrated.

Yet the conversations that stick—the ones I replay later—are different.

For us, it happened during the three-hour drive from Nashville to Benton, Tennessee. With no agenda other than getting there, we meandered through random topics and asked wonderfully pointless questions. There was no expectation, no forced depth—just genuine, relaxed connection.

And that’s the thing: real conversations sneak in when no one's watching the clock or checking a box.

Leadership is no different.

I remember when PayNW was primarily an in-person company. I used to regularly invite leaders along for client visits that involved long drives. Ostensibly, it was about ensuring strong client relationships. But the real reason? Windshield time.

That windshield time was the real meeting, the actual team-building. It was the space where true connection surfaced because no one was performing or strategizing. We were just being, chatting, and occasionally navigating silence—or discovering exactly how many country song lyrics I inexplicably know.

Now, as a remote team, I actively recreate these moments. If I am traveling near colleagues, I insist on meeting for dinner—not just with them, but with their families. Recently, in Nashville, that meant dinner with our CFO and his family (my youngest happily joined).

I also make sure to invite team members along on client trips or conferences. Not because I need backup, but because of the invaluable unstructured time that inevitably arises.

Here's the truth we don’t acknowledge enough: great leadership isn’t crafted during structured meetings or scheduled workshops. It’s built in the margins.

Let’s face it—the best insights rarely emerge from the scheduled brainstorming sessions. They bubble up in hotel lobbies, in line at the airport Starbucks, or during a long Uber ride.

So, next time you’re planning your calendar, I challenge you:

Leave intentional blank spaces with team members. Embrace the unpurposed time.

Because when there’s no agenda, no KPIs, no predetermined goal—that’s when people open up, get honest, and connect in ways you simply cannot script.

And those moments? They change everything.

What about you? Where in your leadership could you trade a structured meeting for some unscripted, unpurposed time?

Give it a try—you might just find magic hiding in plain sight.

Gratefully,