Why I love traveling alone (and meeting new people)

An image from a Miami beer garden where I made a couple of friends this weekend. Pro Tip: Don’t crash the party table; join the group of 1–3 people. They will be more likely to welcome you into their conversation.

I’m on the heels of a weekend trip to Miami, where I traveled to see a good friend of mine in NYC perform in his first leading role since I have known him — starring as Che in Evita at the Actor’s Playhouse. It was unbelievable to see him onstage on Friday night, and well worth the trip. But given that he was in the midst of rehearsals as well as important vocal rest, I only saw him before and after the show on Friday evening. So, for the rest of my weekend, I was on my own, wandering in and out of Miami neighborhoods, enjoying exploring the art scene in a quiet and completive reverie.

Even though I was alone, I don’t find trips like this to be lonely. In fact, I find them to be quite the opposite — invigorating and highly social. After all, it’s easiest to meet new people when you travel by yourself. To me, it’s like solving a puzzle. Where will I end up? Who will I meet? What will I learn? This is the best part about traveling by yourself, and I try to do it at least a couple of times a year.

I believe that everybody you meet has at least one incredible story to share. You’ll either learn something new or be exposed to an entirely different way of looking at things. Think about that the next time you’re stuck in the checkout line at Whole Foods.

So on Saturday when I wound up meandering into a brewery in the Wynwood Art District, I decided to take a pint of beer outside. Yes, there were empty tables. And yes, there were free seats at the bar. But the weather was nice, and I decided to try my luck with making a couple of new friends. So I plopped myself down at an occupied picnic table, where an older couple was finishing up their beers.

Within minutes I learned that they both worked in public finance and had each been a comptroller for one of the three largest cities in Indiana.

• “What can you tell me about how public finance differs from private finance?” I asked them.

• “How does someone with a journalism find her way into working at a VC firm?” they asked me.

She was a Democrat; he was a Republican. They were in town for a conference and had barely made it off Miami Beach. Several years ago, they visited NYC to attend a concert at Madison Square Gardens. Someday, they hope to retire and move to Amsterdam. Yes, Parks and Rec the TV show does accurately depict some of how government works in Indianapolis, including featuring their oldest steakhouse. (I knew it!)

Because we came from such different paths and backgrounds, we all took away something from our conversation. In the end, I gave them my card and told them to look me up on their next trip to NYC.

But before they stood up to leave, the woman looked back at me quizzically and said:

“Okay, I just have to ask…why did you decide to sit here? As an introvert, if I came to a bar like this alone I would have gone and sat in the corner by all of those shipping crates.”

I followed her gaze toward the shipping crates, which were stacked on the edge of the yard next to the dumpsters, and I shook my head and laughed. There’s no way I would have sat over there.

“Well,” I began. “I like meeting new people, so I figured I’d try my luck to see if you would be open to a conversation. And even if you weren’t, you picked the best table outside, with the street-facing view. I figured even if you didn’t want to talk to me, I could entertain myself by watching the Wynwood foot traffic.”

“Wow,” she said. “That’s really brave of you.”

“Brave?” I replied, genuinely surprised. “I don’t think so. I spend most of my days traveling around and meeting new people and talking to them. This is just how I operate.”

This is all true. By this point in my life, I’ve been striking up conversations with strangers for so many years that I hardly notice the fear factor. I thought back to some of my earlier solo trips — all the way back to my first cross-country trip out West as a 13-year-old. My flight connection through Dallas ended up being delayed 4 hours, and I was stuck at the airport alone to wander, buy myself dinner, and explore a new environment. And I loved every minute of it. (Not so much the case for my mother, who stayed up all night from our home in Pennsylvania as she worried helplessly about her stranded little girl.)

During that delay, another passenger thought it would be amusing to persuade me that animals called “Jackalopes” were in fact real in Texas, and I believed him all the way until I got to Oregon and told my aunt and uncle about it. They just laughed and told me to be a bit more discerning about what people tell me. (Side note: This is still good advice.)

From that very first solo trip, there would be so many more — cross-country trips driving myself to school, long train rides of getting seated with new friends for dinner, and business trips to visit handfuls of customer visits in cities I was also meeting for the first time. Even if any of this was brave at first, my interactions with others while traveling has become a habit now. And it’s one that I’m glad that I made early on in my life because it makes traveling so much more rewarding.

On this most recent Florida trip, I met a sales associate from Microsoft’s Seattle HQ, who traveled to Miami to cheer up her best friend after a breakup. I got a private, guided tour of three floors of contemporary art owned by a well-off family who opens their doors to the public. I met an artist who is currently using Clue, one of our USV portfolio companies, to try and get pregnant. I learned a brief history of Cuban art from a gallery owner who has been collecting it for 40 years. I met an antiques dealer who has traveled to more than 100 countries.

Everybody has stories to share. You just have to be patient enough to listen. So the next time you find yourself out alone at a bar, a restaurant, or a tiny boutique shop, I encourage you to linger a little bit longer than you otherwise would and strike up a conversation with someone new.

You might be surprised how easy it is to meet new people once you give them an opening to chat.