Written by Andrea Fulton, Livingston Fellow Class of 2016

The bus lurched to a stop near one of the public plazas in Old Havana. Tired from the early flight and a little overheated from the rush of humidity and insufficient air conditioning, the 17 of us stumbled to the cobblestone and tried to focus on the Cuban history being hurled at us. Nearby, women dressed in flamboyant hats posed for photos with the tourists. The wind blew like crazy and the afternoon sun sank into us. Welcome to Cuba.

When the opportunity to visit Cuba as part of a “fringe diplomacy” trip coordinated by an organization loosely affiliated with the Aspen Institute presented itself, I leapt at it. I barely considered the impact of taking the time off, or the logistics involved in leaving my family for nine days (which I had never done before). I think I had filled out the forms before the invitation was fully articulated. This trip was one of several to Cuba led by a collaborative group from across the country that focused on fostering entrepreneurial activity in emerging markets. It was out of my wheelhouse and right up my alley.

One of the goals of my Livingston Fellowship is to push myself outside of my traditional routine, meet interesting people and dive into thinking about how I can make a difference.

This trip was bound to check all of those boxes.

That first step off the bus marked the moment when the roles began to take shape. The youngest member of the group upheld the promise of his youth by snapping rapid-fire selfies. The organizer of this trip and many others like it, took his post as the animated and responsible chaperone. One by one, the personalities emerged. The question that had swirled in the back of my head since I’d encountered some of my travel mates the night before in Miami finally came to the fore: “How was I going to show up on this trip?”

Like most people, I shift roles several times a day depending on the situation. Part of what attracted me to the Livingston Fellowship program was the idea of digging into which of these roles, or parts of these roles, was important to my growth as a leader. The Fellowship felt like a chance to try things that might help define a path to nurture the characteristics most supportive of my growth. So it seemed only logical that I would begin this adventure a few thousand miles away from home.

I fell in love with travel after college. I hadn’t had the chance to travel much as a kid and when I finally got to see more of the world, I never looked back. But traveling alone – without being part of a pair – was new. A few work trips aside, I had never explored a new place without people who knew me really, really well. Cuba presented the chance to see a new place in the world, meet interesting people, and do it without my typical crew. This, I thought, would force me to spend some time with myself and ponder what I really thought about leadership.

While the trip delivered to varying degrees on all of these fronts, the most surprising outcome of my introspection was the constant struggle between wanting to be in charge and wanting to fade into the background. There were plenty of strong personalities in the group, which was ultimately a relief. Not only did it make for great entertainment, but it meant there was plenty of room for quieter, more observant folks. I realized quickly that I was perfectly comfortable in the latter category amongst this group. I savored feeling absolutely zero pressure to be the life of the party, broker group decisions or babysit. I was content to let others do those jobs. I did, however, struggle immensely with the rigidity and somewhat repetitive nature of the schedule. After a few months reflecting on nine days on a bus fueled by rum and deliberation about the pros and cons of capitalism, some of the gifts of this adventure have begun to emerge.

I remembered how much I love to watch and talk to people. When you travel with companions from home, you don’t always need to meet new people along the way. Some of us do it anyway, but it isn’t as necessary. When you are alone, or with a group you don’t know well, it creates a vast amount of space to meet and get to know people. Trying new things is a bonding experience. That, coupled with the fact that none of us was intertwined or invested in each other’s lives, created the perfect formula for learning things about people that would take years to uncover in the routine of daily life.

I concluded that I can still want to be a leader and not have to make every decision or know the outcome of every situation. I know this is common sense, but it became so clear how much I appreciated not having to find directions to dinner, or plan transportation, or worry about having enough cash for the hotel (because Cuba is cash-only). However, I also realized just how much I love being in control, and this trip helped me realize the difference between wanting to have some control and needing certainty in the outcome. I have always fancied myself a staunch rule follower and, as I analyzed this, I realized it has everything to do with wanting to know the outcome before I dip a toe into a new situation – assuming very little risk. It was a refreshing, albeit surprising, realization that I had a limit for itinerary-following and group participation because I was craving a little less certainty in the outcome.

On more than one occasion, I opted out of the formal program and just explored the city. I walked down narrow streets, took photos, listened to conversations, and visited museums. It was liberating; exhilarating, even. Those moments brought to light my thirst for a wider set of undefined outcomes and also made clear just how little time I spend alone in my everyday life. I rarely slow down and just think, and that is a mistake. Self-reflection leads to gratitude and growth and this trip brought about and excess of both for me.

The feeling of letting go of certainty was a great early discovery in my fellowship journey, and it has opened up a wider set of goals (not defined outcomes) for the remainder of this incredible opportunity.