Thinking Different Questions

“What’s something you now think differently about?”

“What’s something you’ll do next?”

I end each week of Venture Travel by asking these two questions of each participant. Having spent days exposed to the stories, ideas, and missions of a broad group of passionate individuals, this discussion is one of my favorite parts. The simple questions are sometimes hard to answer—our brains are still processing. Sometimes a person talks and their answer emerges. Or one person’s answer brings another clarity.

Answers rarely repeat. It reminds me that the same experiences filtered through individual perspectives lead to different responses.

Asking the questions is less about the answers. It’s a reminder to reflect—as we think about this trip. And the next one. And other life experiences.

Having curated Ventures in four locales (Tanzania, Rwanda, Cambodia, Santa Fe) the answers rarely reflect WHAT we did. It’s more about HOW. We reflect on our common humanity. We discover new empathy. We consider new ways of thinking about how we show up in our day-to-day lives—who we surround ourselves with, how we engage, what we do with our time, money, skills, and one precious life.

As host, I also answer the questions.

The latest Venture took place in Santa Fe. The fact that I hosted a trip in Santa Fe surprises me more than anyone. First, Santa Fe is located in the U.S. Second, it’s a city I visited for the first time during 2020—when I moved to it during COVID. 

In speaking my early trip idea out loud to new Santa Fe friends, I asked myself what they had to be thinking:

“Who are YOU to lead a trip in Santa Fe?”

It’s not that I was making a strategic decision to pivot my Venture Travel offerings to the U.S. It was that I found striking similarities between Santa Fe and the countries where I’ve planned past trips. All are places people like to visit, but we tend to visit through a traditional, narrow lens. In Tanzania and Rwanda, it’s enjoying a safari; in Cambodia, it’s exploring ancient Khmer ruins. 

In emerging economies, a young population and the rapid adoption of technology means things are changing quickly—economically, socially and culturally. Change is most visible in cities—Dar es Salaam to Phnom Penh. Most visitors quickly transfer through these cities. Finding them fascinating, I can’t help but dive in to seek out people with perspectives I need to understand. 

COVID triggered a tidal wave of economic, social and cultural change throughout the U.S. Santa Fe is one of the cities that feels to be at an inflection point. Since moving here, I continually stumble upon new people and perspectives. One morning, I was having breakfast with one of the city’s visionary entrepreneurs.

“Santa Fe is like an emerging economy.”

The sentence rolled off my tongue. He understood exactly what I meant. We weren’t talking about categorizing a place by GDP per capita. We were talking of ideas, opportunities, tensions and complexities that wrap a city at an inflection point. It’s easily missed by the average visitor focused on “must-do” restaurants, museums and art galleries.

I design Venture Travel around consistent themes—technology, sustainability, economic growth, and culture. In Santa Fe, it’s all spiced up with a little chile and art.

The process of designing Ventures fascinates me. When I ask passionate individuals to join us and share their stories with our group, they tend to say yes. In Santa Fe, offers and introductions came to me before I could even ask.

While I design trips for others, I now realize that creating a Santa Fe Venture was key to my quickly cultivating friendships in my new hometown. A coffee meeting or Zoom call didn’t end with “nice to meet you, stay in touch”—there was a project both of us were excited to work on.

While still building out the Venture, I began marketing it. I was plagued by a real concern.

“What if no one signs up?”

I sent out my first invite for the Santa Fe Venture in April 2021. We were coming out of the depths of COVID. Along with most of our friends, Bob and I had just been vaccinated. Venues were re-opening. People were planning travel. But would road trips to family lake houses take priority over immersive small-group travel experiences? Would people save an immersive experience for an international destination? I had to remind myself that the worst-case scenario wasn’t that bad—if no one signed up by June, I’d suffer the loss of time and a bruised ego.

By the end of Memorial Day weekend, I had a waitlist.

I continued to plan, and the trip grew deeper with every new connection. I was as excited as the participants. And I was increasingly excited for them.

At the end of August, 10 curious-minded soon-to-be-friends convened in Santa Fe. And what a four-day experience it was.

So how did I answer the questions—what do I now think differently about, and what will I do next?

Mostly, I was reminded of my role. It’s not to be the expert. It’s to be the convener and the connector. The fact that I’m a generalist and outsider is my superpower. It makes me curious.

Questions—not answers—are the heart of Venture Travel.

And I commit to our reconvening in Santa Fe.

I can’t promise that each Venture will be the same. I can promise that each will deepen with every new connection.

There are new questions to ask.

There are new stories and ideas to explore.

The next Venture Travel Santa Fe is slated for August 24-28, 2022. We also seek to return to international travel experiences. To receive early notice of upcoming Ventures, subscribe to my posts.