How do I become a more interesting person?

Originally posted on Quora, answering the question: How do I become a more interesting person. Follow me on Quora.

“Either write something worth reading about or do something worth writing about” – Ben Franklin

Often easier said than done.

My senior year in high school I sat down for a group interview at a prestigious university. The interviewer asked everyone to share what they did this summer. One girl had spent the summer in London apprenticing under a well known photographer. Another traveled to Italy to study painting. I’d spent the summer in New Hampshire working at an ice cream shop. I didn’t feel the least bit interesting. And becoming interesting sounded very expensive and out of reach.

That’s all changed. Since then I’ve driven across the country 7 times, hitch hiked from San Francisco to LA, attended a Rainbow Family national gathering, backpacked to over 20 different countries among others. I’ve got amazing stories from all of it, but a lot of the best stories didn’t happen because of traveled far or spend a lot of time or money. Here’s what I’ve learned about becoming interesting:

  1. Seek adventure. Adventure doesn’t have to mean traveling to another another country or involving a expensive gear or expenses. One of my most memorable college experiences was hitchhiking from San Francisco to LA. It cost me nothing. I caught somewhere around 10 rides and have a story from each. I’d never hitchhiked before or after. I also took a Greyhound from LA to Santa Fe once and could write a book on all the people I met and stories that happened. The ticket cost me $35. Seeking adventure can be through travel, sports or the outdoors, but it definitely means getting out of your comfort zone.
  2. Be curious. Be curious and learn about the world around you. Read, listen to podcasts, find great websites. Learn from interesting people. Knowledge has never been as accessible as it is now. Knowledge is one of the sources of having interesting things to talk about. You might find an interest in say Astronomy. You could show friends common sites in the night sky and the incredible stories behind them.
  3. Be unconventional. Capturing people’s attention doesn’t have to involve grand stories or adventures, but can come from the unconventional. Triathlons weren’t common right after I got out of school. If you did them then, that’s pretty interesting. Then Team in Training came along (an awesome cause and not taking away anything from it), and suddenly it seemed everyone around me was doing triathlons. Not really that interesting anymore. A friend of mine after college did something no one’s ever done before (at least known). He circumambulated Martha’s Vineyard via its beach/shore. It only took a couple days and some camping gear. 20 years later he still tells the story. He also lived briefly in a Teepee after college. That part is interesting enough. It gets more interesting considering his stay there continued through a cold New Jersey winter. Another friend does long bike tours all over the world (at home in the U.S. as well). That’s pretty interesting. What makes it even more so, is he does it on a beach cruiser.
  4. Delve deeply into a hobby. Interesting people have hobbies they pursue passionately. It’s hard to have more than one or two that you have the time to pursue passionately, but one is all you need. Immersing yourself in hobbies is inherently interesting. You meet other super passionate people, you travel with a purpose and you have shared experiences. I got into scuba diving because I loved the ocean, and I imagined it would be something I did once a year on tropical vacations. I now dive 12-15 times per year in California alone. Primarily off the beaches in Santa Monica and Malibu to hunt for lobster and to spearfish. 50 feet off of beaches packed with tourists, I’ve caught lobster and fish and swum with seals. I bring a camera along to capture it. There’s not a single person I show the photos and video to that isn’t captivated by them and amazed it’s all possible yards off the local beaches.
  5. Explore. I was going to just say “travel,” but exploring is much more interesting. When I was backpacking through Guatemala, taking bus’ around the country and staying on youth hostels, the entire trip was an adventure. A couple approached me. They were on a cruise and were being shepherded around to the touristy sites with hundreds of other people from their cruise. They were amazed and jealous at the freedom I had to see and explore. We were in the same place, they were on a tour and I was exploring. Traveling to Asia, I had an extended layover in Kyoto and hired a taxi driver to take me to the Zen monasteries, he took me to two hugely popular monasteries that although they were beautiful, were immensely crowded and touristy. It didn’t feel like the spirit of Zen at all. I asked him to take me to a quiet monastery. He brought me to one with only a couple other tourists. It had a large beautiful rock garden and empty halls and spaces, and it left a much deeper impression than the touristy ones. I could write pages and pages on this topic, but the key point is to get off the bus, the schedule, the tour and to go explore.
  6. Document and share. It’s much more powerful to show an amazing adventure or trip or experience than it is to try to describe it. I make a habit to document and take great photos of all my trips and to have those photos and videos ready on my phone in albums.
  7. Learn to ask questions and listen. If all you do is talk about yourself and tell stories, you’ll be a huge bore. It won’t matter what you’ve done or where you’ve been, people only really want to hear stories about you to a certain extent, then they want to talk about themselves. Every time I talk about the hobbies or travel, it’s usually a jumping off point to a great conversation where we both share about what interests and fascinates us. You can actually pull this off without having any interesting experiences, just by learning to ask great questions and to listen well. But I wouldn’t recommend bypassing the experiences, because there’s an immeasurable value of actually going out and having these experiences. And it’s not in becoming more interesting, it’s in expanding your perspectives and experiencing the world.

Looking back on that college group interview, I’d felt hugely insecure. I realize now that I was very interesting. In high school, I’d been a student leader and an accomplished athlete. I’d spent my summers working at an ice cream shop and training for road bike racing by riding up to 200 miles per week. It took having all these later experiences to realize that it’s the sense of adventure, passion and curiousity that makes people interesting, not their experiences or where they’ve traveled.

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