Facing Fear and Cultivating Courage with Jessica Nabongo

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The first person that pops into my mind when I think about facing fear and cultivating courage is Jessica Nabongo.

In October of 2019, Jessica became the first Black woman on record to travel to all 195 countries of the world. From leaving her 9-5 to traveling to places that the media has painted with fear and panic, Jessica is the epitome of courage and a go-getter attitude.

Aside from this huge accomplishment, Jessia is an entrepreneur who runs a popular blog called The Catch Me if You Can. She also started the lifestyle brand called The Catch and is in the process of writing her first book.

You’re in for a treat with our conversation today as Jessica shares her motivation for traveling to every country in the world, her relationship with fear, and how she cultivates courage in everything she does.

Jessica Nabongo 01 | Facing Fear and Cultivating Courage

Facing Fear and Cultivating Courage with Jessica Nabongo

If you’re looking for inspiration to go out and do the things that scare you, look no further. Jessica is the perfect definition of a woman who lives her life by her own design.

In fact, she was ready to leave a great job with the UN in Rome that offered stability and a great income in pursuit of her passion.

The concept of being a digital nomad and working remotely was virtually nonexistent when Jessica decided to take that leap. 

However, her employers didn’t want to let her go. So she decided to come to a compromise that would allow her to keep on working while being location independent. 

“I sort of created that life for myself without a blueprint. Because people weren’t doing that on the internet. I just love my freedom. And I created that flexibility for myself.” 

Jessica Nabongo 02 | Facing Fear and Cultivating Courage

Creating Her Very First Company

Eventually, Jessica ended up moving to Rome because she was offered a great post there. But after Rome, she moved to DC to work at a consulting firm. And that was the last time she was employed by someone.

When she finally quit her consulting job in 2015, Jessica created her very first company called Jet Black. Jet Black is a luxury boutique travel agency that worked with high-net-worth individuals.

“My parents were not business owners. So I didn’t have anyone ask. And most of my friends were working regular jobs. So you know, it was a lot of trial and error.”

Luckily, Jessica had some savings to hold her over. She also has a keen eye for branding and was able to build a website and establish her company’s presence. 

“But it was tough in the beginning because I didn’t know what I was doing. It was the first time I was working for myself.”

Jessica kept traveling, shooting content, and blogging throughout the process of starting Jet Black. And even though she used Instagram to build Jet Black, her personal brand and Instagram account probably had less than 1000 followers.

“My jet black account became huge before I ever focused on my personal brand. But eventually, after I got success with Jet Black, I decided to make a pivot. I was still running Jet Black, but I decided to pivot and focus on the business of being me.”

Jessica Nabongo 03 | Facing Fear and Cultivating Courage

Jessica’s Slow and Steady Growth on Instagram

Looking at Jessica’s Instagram page today, you might think that her journey to 195 included several sponsored stays. However, it was only in 2018 (one year before Jessica completed her journey around the world) that she started to truly focus on her personal brand.

“From 2017 to 2019, it was mostly Jet Black that was funding my life. I was very slow to make money via Instagram. Luckily, because I had been featured I’ve been writing for some travel publications, I was getting a few free comp hotel stays. I only ever had one free flight out of all those flights. And that was the South African Tourism Board. But outside of that, it was me. That was Jessica Nabongo paying for it with my savings. It was credit card rewards and the income that I had from Jet Black.”

Not landing deals with tourism boards was incredibly frustrating since Jessica knew she had a great Instagram and she was doing incredible things. But the power of her community came through when she decided to launch a GoFundMe campaign to help her accomplish her goals.

“In October of 2018, I ended up doing a GoFundMe, which was great. Because people wanted to see me win. I’m still mind blown. And I mentioned it in the acknowledgments in my book. Over 200+ people donated over $20,000. It very much became the people’s journey, it wasn’t just mine.”

Jessica Nabongo 04 | Facing Fear and Cultivating Courage

Facing Fear and Cultivating Courage at Every Turn

Quitting a stable job to pursue the digital nomad lifestyle when the concept didn’t really exist.

Traveling to every single country in the world.

Starting a company without any guidance or experience in entrepreneurship.

These are all things that come with a lot of fears and require a lot of courage.

Jessica admits that she’s a risk-taker when I asked her how she’s able to constantly face fear head-on. “My parents created so many little safety nets for me, which I’m super grateful for. So no matter what, if like I lost all my money, I can go back to my mom.”

When it comes to the fear of quitting her job, Jessica says “what’s the worst that can happen?”

“I’m a smart girl. I try not to burn bridges. All of the jobs that I left would happily have had me back. Some of them I did go back to.”

“For me, I just live a life where I strive for excellence in everything that I do. I maintain relationships, which means I gain the ability to always find income. I think that’s what it is. So I don’t have to be afraid to take a leap. Because I know I can figure something out.”

When it comes to facing her fears on the road, Jessica says that as a Black woman, America is the riskiest country she’s spent time in.

“The worst things that have happened to me have happened in the US. When I think of my time in Somalia, Afghanistan, and South Sudan, I never was afraid. I was super comfortable and met really amazing people. I realized very early on there’s less to fear outside of the country (USA) than inside in terms of my personal safety.”

Jessica Nabongo 05 | Facing Fear and Cultivating Courage

Managing Your Fear in Everything You Do

This conversation with Jessica will not only inspire you to face your fears and cultivate courage, but it might just give you the travel bug.

Aside from Jessica’s inspiring story, I had to ask her about her favorites around the world. From the country with the best foods to the country that surprised her the most, this episode is a fun listen for anyone who likes a little mixture of business and adventure.

So click the player below, tune in to the episode, and get caught up with Jessica’s adventures around the world.

A glance at what we discuss:

  • Why Jessica decided to visit every single country in the world (3:37)
  • Transitioning from a secure 9-5 job to working remotely to starting her business (6:21)
  • Jessica’s process of earning an income as an influencer (10:38)
  • How Jessica manages and faces her fear (12:35)
  • What other countries do better than the US (14:57)
  • Does Jessica still have the itch to travel? (18:55)
  • How Jessica’s business and life changed and pivoted during the pandemic (21:11)
  • The process of writing her book (24:31)
  • Top lessons about life that Jessica learned from traveling the world (27:27)


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