It’s 1pm in Detroit and 7pm in South Africa when writer, public speaker, photographer, entrepreneur, and travel expert Jessica Nabongo and I speak for our interview. I’ve caught her at her “base”; her hometown and the place in which she grew up. It’s where she recharges before and after each epic trip. She’s just returned from a work trip to Paris, and I’m interested to know how she relaxes and re-energises before heading out into the world again. “Typically I have something else coming up, but it depends on how long I’m home. Luckily, I’m here for nine days, so I’ll do nothing for 48 hours, and after that, I come out of my little cave. My suitcases are flung open but I’m not unpacking them. I don’t start working out until after a couple of days when I find a routine, which includes meditating, cooking, and exercise,” she says.
Jessica’s story is simply phenomenal – a triumph of the unimaginable for most and one of perseverance, determination, and hard work. Years of endless flights, many airports (296 over the past 11 years to be exact), numerous bus and train stations, maps, new languages, food and adventures later, Jessica is a pioneer who reimagined the archetype of the modern-day female explorer. It all started in 2017, when Jessica went on a twoweek getaway to Bali. She’d recently left the corporate world to be an entrepreneur and came across an article about a traveller who had visited every nation on Earth.
Jessica realised there were others who shared her desire to travel the world, and her goal was to be the first Black woman to do it. “I did my undergrad at St John’s University in New York and then came back to Detroit and worked for two years for a pharmaceutical company. After that, I moved to Japan and taught English for a year. That’s when I started blogging; this was in 2008 – Instagram didn’t exist, Twitter had just started, and Facebook was what people were using. There were no apps on phones. The iPhone had only recently come out. When I left that job, I went to grad school and decided to just travel. I started my new blog – thecatchmeifyoucan.com at that time. I was just travelling and blogging, and I later went to grad school at The London School of Economics.
After that, I ended up moving with my then-boyfriend to rural Benin and worked for an NGO. We were there for about six months, and then I got a job working for the Food and Agricultural Organization of the United Nations. The headquarters are in Rome, so I was travelling and working, and then I got a great job offer in Rome, so I ended up going back there in August 2013. I was there for a couple more months before I quit the UN and moved to Washington DC. I hated every second of it. I quit that job in 2015, and that was the last time I worked for someone. I wasn’t scared, but I asked myself what I was doing.
When I started blogging, there weren’t many people doing it. I wasn’t even doing it for the public, but for my friends and family to stay updated. Strangers started reading it, and I was like, ‘that’s so weird, why are people reading my blog’?” she recalls. “I’ve been travelling internationally since I was four, and I knew in my early 20s that I wanted to visit every country,” shares Jessica. “In February 2017 I set a deadline to finish my mission by the time I turned 35. And I did it! A lot of times, people say they want to do something and get stuck in the planning phase; they get so caught up in trying to make sure everything is exactly right that they either delay or never do the the thing they wanted to do. I didn’t have anything figured out. I didn’t know how I was going to pay for it, but I knew I’d figure everything out along the way.”
Jessica financed all her travels by combining savings, credit-card rewards, a Go Fund Me page, and earnings from establishing her own travel agency. “I accumulated frequent flyer miles during my travels,” she explains. Today, she works with tourism boards around the world, and regularly travels for speaking engagements. At the start of her mission in 2017, Jessica had already visited 60 countries, which meant she had 135 to go. She began her travels by accompanying her Ugandan parents camping around the US, and on trips to places such as Canada, Mexico, and Jamaica, as well as visits to their home country, Uganda. It’s evident that when her parents gave their young daughter the travel bug, they had no idea what they were starting. In navigating her way through all these countries, Jessica says she tries to immerse herself in every way, but is also aware that she’s an outsider and doesn’t delude herself into thinking otherwise.
To get a thorough know-how of each culture she visits, Jessica is always conscious of connecting with local people. She never wants to offend anyone by coming into their country and acting like an expert in their territory and knows the importance of staying curious and asking questions. “A lot of people hear my voice and say, ‘Of course she’s American!’, but I don’t think about the world the way most Americans do. A big part of that is because I’m Ugandan, and even though I grew up in the US, I very much grew up in a Ugandan home and part of a wider African community. The amount I travel and the experiences I’ve had have made me more empathetic and have allowed me to move through the world with much more grace. I don’t see the value in hierarchy,” she notes. ‘Do we still celebrate “first Black”, and does it really mean anything in today’s world?’, I think out loud. Jessica gives a resounding “Yes!”, adding, “A lot of people need a blueprint to do things. That’s why I think the “first Black” thing is celebrated. What sets us apart as the first ones to do certain things is that we don’t need a blueprint. We’re doing a thing that’s based on passion or interest. We’re doing something that sits inside of us. The beautiful thing is it has inspired other people – not just Black people, everyone. It serves as, I hope, a symbol to people that you can do whatever your heart desires. I’m not here to inspire or encourage other people to visit every country in the world. I’m here to show people that you can create the life you want to live and everything you need to do it is inside of you.”
Female adventurers who are pushing boundaries and setting records are on the rise, and solo travel for women is becoming increasingly popular. But it is impossible to not mention safety when it comes to travelling alone, even for pioneers such as Jessica. She shares that, although always vigilant and cautious, she follows regular safety tips like any other tourist. Jessica has, sadly, experienced a few frightening moments safety wise. In Miami, a police officer pointed a gun directly at her face. In Paris, someone attempted to snatch her phone right out of her hand. And while in Rome, she was terrified when a taxi driver made an unwanted advance by trying to kiss her on her mouth.
Her blog, Catch Me If You Can, has since been turned into a book with National Geographic. “Publishers rarely reach out to people to have them write books, so I was very grateful that they reached out to me. Most of the stories [in the book] aren’t on my blog. The book has 100 stories from 100 of the 195 countries I’ve visited, and there are tips, with lots of images,” Jessica says. She doesn’t like the ‘best and worst countries to visit’ question and explains that everywhere deserves to be visited. “I can tell you the places that I enjoyed visiting, but I wouldn’t label them as the best places to visit in the world. Some places I find myself going back to are Cuba, Senegal, Japan, Italy, Kenya, Brazil, and Jordan.” As for advice for those wanting to follow in her blogging footsteps? “The important starting point for travel blogging is asking yourself what is your why,” she says. The why for Jessica, back in 2007 while working for a pharmaceutical company, was the question we all ask ourselves at some point: Is this all there is? The difference is that she didn’t just sit with the question but took action in changing her reality and realising her dreams. The rest, as they say, is a stack full of stamped-passport history.