In this series, we’ve been exploring what it looks like to approach leadership with a journey mindset. Journeys begin with possibility, and they move through recognizable patterns. But along the way, they also invite surprises.

Sometimes those surprises feel delightful. Sometimes they’re inconvenient or even disruptive. And yet, surprises are part of every meaningful journey — shaping us, stretching us, and reminding us that leadership is rarely a straight path.

The whole family still talks about it—the time I forgot my wallet on the kitchen table—90 minutes away—from our flight to Disney out of Portland, Maine.

This was in the early years of travel being impacted by TSA. And it turned out we had a friend in the Portland airport who worked for TSA. Who just happened to walk by as we were discovering my missing wallet and wondering what to do.

“You will be able to get to Disney, Emily, without your ID. And I can’t tell you why or how I know, but you won’t be able to get home without it.”

Our very next steps aren’t clear in my memory, but what I do know is that I changed my flight till a later time, left my family at the airport, drove the three-hour round trip, and found my family in Florida later that day.

And I remember giggling in the car as I drove up I-95.

Because what else could I do? I could have fumed. I could have cried. I could have allowed my internal voice to call me all kinds of badnames.

That giggle mattered. As leaders, the first reaction we model in surprise moments sets the tone for everyone else. A pause, a smile, or even humor can steady a situation that could otherwise spiral.

Meanwhile, Marc was navigating flights from PWM to LGA, from LGA to MCO. And the kids were 3, 6, and 9. Which was fine until Marc had to figure out how to help the two youngest go into the bathroom in LGA by themselves in the days before family bathrooms.

But we all got to Disney. And we all still talk about it today.

Any journey, no matter how well-planned, will hold surprises. The leadership question isn’t whether surprises will come, but how we will receive them. Will it end the journey? Will it become a shadow on the journey? Or will it become a part of the journey that we learn and grow from?

Preparing for Disney began weeks before the trip. It wasn’t our first visit—which helped, because we knew what to expect for a lot of the day. But it was the first trip with the kids at these particular ages. I am a check-double-check kind of planner. We had a grocery list already written out for Walmart, snacks packed, and a general idea of which rides mattered most to each of us.

I would have checked each bedroom at least twice to make sure things were turned off, unplugged, and water not running. I would have looked to make sure all the pieces for a good trip were in the van and peeked under pillows to make sure favorite books or stuffed animals weren’t forgotten. I am that good at the Travel Mom job.

And yet. My wallet, with my ID, remained in Waterville, Maine.

That’s another leadership lesson: even the most careful planning cannot eliminate every surprise. When things slip through, the question is not “Who messed up?” but “What does this make possible?”

We were at a time of life when I was doing a majority of the kid-wrangling. So I was delighted that Marc was going to get a different experience with the kids. (I didn’t think of how scary an LGA public bathroom might be.)

Sharing responsibility in surprises often brings out strengths that otherwise remain hidden. When leaders let others step in, they discover who else on the team can carry the load.

It was also going to be a new adventure for me. I didn’t travel alone—ever. I depended on Marc’s expertise and enjoyed (mostly) just following directions. But today, I was going through airports, on plane rides, and to the Disney resort all by myself. I don’t think I had ever been able to take the time to just watch out the window of the Disney bus before because I would have been attending (happily) to the needs of my family.

Surprises can reframe roles. They may push us into spaces we didn’t expect, and in those spaces, new confidence grows. Leaders who reframe inconvenience as opportunity often come out stronger and more focused.

By the time the bus pulled up to the resort, I was rested and focused. I was excited to see my family (if I could find them). And the family was settled into our condo (I hadn’t had to do any of the unpacking) and were at the pool blowing off steam and beginning our week of play.

We were all actually in a better head and heart space on our first evening of a Disney vacation than we had ever been.

That’s the final lesson for leaders: surprises don’t just interrupt the plan; they sometimes create a better outcome than the plan itself.

As we’ve seen, journeys begin with a possibility, they move through recognizable patterns, and they invite surprises along the way. Each of these moments calls leaders to respond with awareness rather than reaction.

Take a moment this week to reflect:

• What surprise has shifted your leadership recently?
• How did it stretch or shape you?
• What new possibility might be opening because of it?

Just as in any journey, surprises aren’t detours from leadership — they are part of it. And often, they become the very stories that remind us we’re growing.