One Personal Item and One Carry On

(The following is a reflection from the Reset Retreat. One of our Guidelines is to be keepers of stories. Out of respect for that, I will share this from my perspective and leave out any identifying names.)

Before you board a flight, the airline repeatedly announces that each person is allowed one personal item and one carry-on. Yet, without fail, someone always tries to board with more than two items.

They get pulled aside, informed that they must consolidate, and then I witness them trying to force that small item into another bag. I understand the policy, but I also find the entire exchange comical. There’s something about watching a person try to cram one more thing into something that’s already full that leaves me shaking my head.

When I can, I fly to work events. But for the second annual Reset Retreat, I drove. I had two Rubbermaid tubs in the trunk of my car that were packed with all the supplies and items we might need for our time together. It was too much luggage for a flight.

On our opening day, one by one, they arrived. The participants were all carrying something – literally. Backpacks, purses, journals, folders, and Yeti mugs were all in tow. But of course, they were also carrying things we couldn’t see: questions about how the day would unfold, fears that they wouldn’t fit in, and anxiety about the processes we would use.

Most moved cautiously. They didn’t know each other yet, but slowly, I watched the room begin to shift. There is something magical about watching strangers connect. Two women who had been in an online group I hosted for the past four years met in person for the first time. A former athlete hugged a coach she hadn’t seen in years. I heard comments like,

“Wait, that’s where you work? My company volunteers there!”

“You live where? That’s near where my family vacationed when I was a kid.”

“You’re in education too? Oh—I thought I would be the only educator here.”

These micro-connections matter because they change a space. These tiny moments invite people to exhale. To set something down—not just their backpacks or journals, but all the emotional weight they carried into the room.

Occasionally, someone will challenge me on the retreats, masterminds, and cohorts I host. They ask, “Can’t I just do that work by myself?” Yes, you can. And there are times when solo work is necessary. But I’ve learned that something powerful happens when we do inner personal work in the context of a community. There’s a difference between a private and a public realization. When others are present for our lightbulb moments, it makes the moment more real because others saw it too. We need witnesses.

On the second day of the retreat, after spending time in small group conversations, I noticed that one of the participants returned to the main room looking physically different. She didn’t go from having her hair down to pulling it up. She didn’t switch from wearing glasses to taking them off. And she certainly didn’t leave the event to go get a facial!

But something about her looked different.

I invited the group to share what they discussed in their small groups. This participant raised her hand and said her group had helped her. They noticed something about her life that she had never noticed before. She said something like, “I don’t have the words, but my group helped me to set something down. I feel lighter. Yes, I feel lighter.” She exhaled and smiled.

I could see that lightness in her. That was the shift I sensed—not her hairstyle, but the way she carried herself. It’s not that everything was solved. But something had been named. Something had been set down. And that moment had been witnessed. The transformation was visible.

And that is what happens when leaders commit to working on themselves. Because the truth is, when leaders don’t heal themselves, we all pay the price. We dance around their wounds. We hope not to trigger them. We absorb the confusion they have yet to process. We carry what they refuse to carry for themselves.

But when leaders take a couple of days to work on themselves, we all win.

So maybe the airlines are onto something. One personal item and one carry-on is enough. Not just for traveling on a plane, but for traveling through life.

The stories. The pressure. The expectations. The pain. The old narratives that no longer serve us but stay with us anyway. Maybe it’s time to travel through life carrying less.

Not because of a rule but out of self-respect. Because transformation isn’t about adding more—it’s about learning to set down what we no longer need to carry.

Travel light, friends.