You see these badass influencers crushing it on the gram and know they got a story to tell. Not the branded narrative promoting a product or service (no shade) but the important stuff like, why they think it’s important for women of color to travel, or how to discover the best of a destination in a short period of time. We cornered your favorite Globetrotting Stilettos and asked the burning questions we know you want answers to. 60 seconds is all you need to walk away feeling satisfied.
GTS: Jessica, you’ve traveled to 6 continents and 63 countries, we need a snapshot of something magical you experienced on your last international trip.
Jessica: I can’t remember my last trip, I’ve been too many places, but, we can talk about Cuba. The one thing that was magical for me was being able to explore a country that has been blocked off to the United States for five decades. I decided to go for my birthday with 17 of my friends and during our stay we met a tobacco farmer. The interesting thing about tobacco farmers in Cuba is that they grow and cure their tobacco and the government comes and takes 90% of the crop, which is insane! They take it to Havana, roll it and place gold label stickers on the now expensive Cohiba cigars. The government sells them, keeps the profit, and the farmers are only left with 10% of the raw product, which they end up rolling and selling in the regions they live in. Legally, they are not allowed to sell outside of this area. Even though many of these farmers are extremely poor because they spend a year harvesting and curing tobacco and then almost all of it is taken by the government, their spirits are still whole.
GTS: Life altering experiences are inevitable when you travel as much you do, care to share any standout moments?
Jessica: One thing I’ve learned during my travels is that the rest of the world is not consuming the way Americans are. Americans tend to be very materialistic. During my 10 years of globetrotting and living abroad, every time I return to the U.S. I notice many of the conversations are different. I realize the things that matter to many people here are shoes, clothes, and material possessions, not spending time with the people you love and being present in the moment. I lived in Italy for three years and in Italy you sit down with your family for dinner everyday, even as an adult. You don’t eat and watch television, or eat while walking down the street. Eating is about community, memories, family and love. Travel has changed my outlook on life. I will continue to put my financial resources towards travel and the things I truly value in life, and place a much lower value on material goods.
GTS: That’s real. You’ve lived and worked on 4 continents, where do you see yourself settling permanently and why?
Jessica: That’s such a hard question! Honestly, I still don’t know. Permanent to me sounds a little scary because I am so used to traveling. I am definitely looking for somewhere to settle down in the near future, but at this point I am still deciding. I have a list of where I want to live, but I also have a list of where I don’t want to live. I want to be around black people, so I definitely can’t do Asia. I also can’t do rural areas, I need to be in a city. I narrowed it down to a city in Africa, Europe, or the U.S.
GTS: What does being a Globetrotting Stiletto mean to you?
Jessica: When I hear the words Globetrotting Stiletto, I envision jet-setters who are feminine, fashion-forward, and embody empowerment.
GTS: Yaass! Do you consider yourself a Globetrotting Stiletto?
Jessica: I do. The idea of being fashion-forward while traveling is something that I can relate to. I always want to be super comfortable but I also want to be cute. When I travel, I try to pick things up that I can easily incorporate into my everyday style. When I travel to Uganda, my ancestral home, I always picks up fabric and have custom clothing made while I am there. Colombia, Benin and Senegal are great for accessories!
GTS: Nice. So that leads into the next two questions. You have a great sense of style, what inspires and influences your creativity?
Jessica: My Ugandan heritage for sure and just the continent in general—the bright colors! I try to always wear bright colors against my dark skin. For me it’s about celebrating who I am and feeling confident. I also think it’s a personality thing too. I have a big personality and I feel like bright colors compliment that. I strongly believe that how you appear on the outside is a reflection of how you feel on the inside. Because my skin is very dark, whenever I wear bright colors, people react. I’m very bold and unapologetic about who I am. Sometimes when we step out into the world, we tend to shrink and I refuse to do that. I am always going to be seen in a bright or print dress and a vibrant red lip. That’s how I stand out.
GTS: Speaking of style, what’s your best-kept shopping secret? What continent, city, or town do you find the best buys? We need intel!
Jessica: I like street vendors at markets in different countries. I don’t shop much in the U.S. If I do it’s Madewell or ASOS.
GTS: You have a Bachelor’s in English Literature and a Master’s in International Development, we tried to guess but couldn’t figure it out. What do you do?
Jessica: That’s a good question! I travel, I write, I photograph and I am the CEO of my own company. Right now, my primary focus is on Jet Black, an elite travel service. I still have the Catch Me If you Can, which is my personal travel blog, but Jet Black is where my energy is going. Prior to this, I worked with the United Nations, doing the corporate thing, but I eventually realized that I cannot work for someone else at this point of my life. I need to do my own thing.
GTS: We get it. Good for you! Pursuing entrepreneurship is no easy feat. What exactly is Jet Black?
Jessica: Jet Black is a boutique travel firm that works with individuals, governments and brands. We focus solely on encouraging tourism to countries in the African diaspora, South America, Central America, and the Caribbean. Funny story on how we got started. I was talking to a friend (J. Cole) backstage at his concert and I was telling him “yo, you need to go to Africa” and he told me to plan the trip for him. I did, he went and that’s how Jet Black was born.
GTS: At what point did you feel compelled to begin documenting your travels? Or did it just happen organically?
Jessica: It was February 2008. I was moving to Japan and it was my first time living outside of the country. I started a blog for my friends and family to keep up with me. After I left Japan, I ended up taking eight months off to travel, so I just kept up with it. During that time there was no WhatsApp where you could easily contact people. Facebook was the only social media available, so the blog was the easiest way to document my journey and give people access to me.
GTS: What does a typical Saturday night look like for Jessica?
Jessica: Typical? There is no typical Saturday night for me. I am very lucky to have cool friends, so I do find myself out and about more often than not. I could be sailing off the coast of Italy one Saturday and then at a rooftop party in Brooklyn the next. I never know what my Saturday consists of until it comes.
GTS: We like that! So, Jessica, what’s your overall travel goal?
Jessica: I’m trying to get to every country in the world! But, short-term travel goal, I want to get to 100 countries before the age of 35. I’m at 63 right now. By the end of 2016 I plan on visiting Norway, Ireland, Northern Ireland, South Africa, and Mozambique. So at least 5 more this year. It’s going down!
GTS: We hear that! Finally, what’s next for Jessica and Catch Me If You Can?
Jessica: Catch Me if You Can is on a hiatus right now. My primary focus is on growing Jet Black. My goal is to make sure that black people are seen and heard in the travel space all over the world.
Keep up with Jessica and all her travels on Instagram: @jnambowa