By: Makayla Dilliner
Traveling is an experience that most may wish for, but not everyone gets to have. From money to time to fear, especially for women, it may be a daunting process to solo travel around the world. However, a Kalāheo alumna from the class of 2004, tells a different story. Having been to 80 different countries and each continent, Kelley Lewis, founder and CEO of Damesly, shared how she was able to leverage her love for traveling and create businesses that fund her passion. Like many growing up, Lewis did not get the chance to travel due to a common constraint—lack of funds. After moving to the mainland and graduating from Arizona State University in Journalism, Lewis decided to start a life in traveling: “I always wanted to travel.
But growing up in Hawaii, it is not a cheap thing to do especially in a family of six so always remember wondering what else the world would look like. When I moved to the mainland, I realized I could just drive for days on end which opened up possibilities of what else the world had for me.” Lewis recounted an experience while living in New Zealand, one that not only confirmed her love for travel but her purpose: “One night I had a dream that I was looking at a hot pink guidebook. And the book was called Go Girl Guides. I remember telling myself in the dream that this is your calling. I never looked back.” Through the company Girls Go Guides, Lewis made it her goal to help women who want to travel overcome their doubts and fears. She explained, “I started to think back on all the times on my travels. What would have been really great to have from the perspective of a solo woman who had been there before? My guides were the first to cater to women and three months later I was writing the first guidebook in Thailand.”
Creating her first business that quickly grew, Lewis developed another travel opportunity. After moving to New York City, she wanted to connect with travelers in an expanded way.
“At one point, we had maybe 15 different staff writers and we did guidebooks for Thailand, Argentina, Mexico, London, San Francisco, and India, and then the business evolved for me. I wanted to connect with even more people in the travel world. I ended up starting a conference called Womenʻs Travel Fest that I ran for around 10 years.” But Lewis made it clear that it wasn’t experience or special credentials that led her down the path of running different businesses and events. Instead, it was a passion for doing what she loved and trying new things.
She considered how it all happened: “I had no real business doing any of these things. I was not an event planner. Iʻd never planned an event in my life. I was not a publisher. I had to figure out how to do that. You know, I knew that I loved to write and I loved to travel. And I kind of just ventured down the path of those two things, that I loved to see how far they could take me.” Lewis gave a rundown of the different places she had traveled to. While each has a different story, every single one holds the same message:
“Iʻve been to all seven continents. And Iʻve seen all seven wonders of the world. Iʻve had such amazing life-changing experiences. From watching the sun come up in front of the pyramids in Egypt or watching the sunset in a hot air balloon in Kenya. Iʻm so thankful for following the passion that I had, which was to travel and seek what else the world had for me. “But what Iʻve realized in going out and traveling the world is that people are mostly good.
And the world is mostly safe. I think that there are far more people in the world who will step in and support you and help you out when you need it than there are people who will try to exploit you and take advantage of you. And that is just what travel taught me about the
World.” Now, Lewis runs a world touring company specialized for women called Damelsy. Explaining the details, she says, “We do small group boutique tours for women, we take a maximum of 12 ladies at a time. We go all over the world, we do a lot of Middle East, a lot of Africa. Right now, we’re doing trips where weʻre teaching photography, for example, photography through the Grand Canyon, or creative writing, which weʻre doing through horseback tours, we call it riding and writing. We are really trying to combine growing skill sets with traveling the world.” In her interview, Lewis made sure to give advice to students who dream of traveling the world or even becoming entrepreneurs.
“I say go out there and chase it. Now I very clearly and freely say Iʻm a CEO, and I run different businesses, and I grow them and sell them and start them. And I think we always tell ourselves that we need different certifications or something to be able to do things. I hope that my story is proof that you go out there and do it. Donʻt let anybody tell you you canʻt figure out how to do it a long way. “Itʻs about taking opportunity into your own hands. And for me, thereʻs really no limit to the amount of things that I can do or the amount of money I can make– the skyʻs the limit. And itʻs really just me, my creativity. In the end, thereʻs no right or wrong, just continue forward with what feels best for you because there are so many new opportunities that exist career-wise for the upcoming generations.”