How to Work and Travel: Get Ready to Grab Your Passport

Jenna Kutcher 

posted by:

Previous Post




November 11, 2019



Imagine hopping on a plane to your next destination, your laptop as the only office you’ll ever need, and building a life and business that not only supports travel, but requires it. The life of a digital nomad sounds pretty glamorous. And in part, I bet it is. But if there’s one thing I’ve learned from speaking to all our guests on this show, there’s always more to the gorgeous Instagram feed.

Jessica Nabongo is the first documented Black woman to travel to every country. All 195 of ‘em. I’m totally enamoured by Jessica’s story. The way she documents each country on Instagram and her dedication to important causes along the way has opened up a whole new vision of travel for me. And once you hear her story, I think you’ll be itching to travel in a new way, too.

How does life work as a digital nomad? What are the keys to safe and productive solo travel? How do you get your boss to let you work from home… And then from across the world? I’m asking her all these questions and more.

This is a story I’ve been so excited to hear myself, so I’m honored to welcome and share with you, Jessica Nabongo.

Where the Love of Travel Began

As the daughter of Ugandan immigrants living in Michigan, Jessica learned to love travel from her parents at an early age. Her first international trip was to Canada (just across the river) but nevertheless, it was the open door and introduction to travel.

She traveled throughout her childhood and in school, and earned a degree in NYC before returning back to Michigan. Jessica landed a high paying job, bought a home, and was set in the American Dream life… But she wasn’t happy.

Around the time she was due for another promotion at work, she hit a wall. Her bonus wasn’t as high as she anticipated, she wasn’t enjoying the pharmaceutical sales life, and decided that day to apply for a job teaching English in Japan. And she got it.

A few months later she put in her resignation, shaved her head, and moved to Japan. Jessica had never been to Asia. That was the beginning of the 195-country journey.

Quitting to Travel

Jessica told me all about her country-hopping after quitting her job in Japan. She had saved up enough money to travel for eight months, and she spent that time between Australia, Fiji, Italy and beyond, landing where new opportunities pulled her. She earned her masters at the London School of Economics. She moved to Africa with her boyfriend until a new internship had him moving to a remote area of Kenya and she decided to return to Europe.

Jessica got a job at the United Nations in Italy but it wasn’t long before she had the itch to travel again. Jessica tried to quit her job, but instead, arranged with the UN to work remotely. That remote work lifestyle suited her for a while because she was able to travel, maintain her salary, and she didn’t have to pay for housing.

“But then I quit again!” Jessica laughed. There’s a trend with Jessica. She quits jobs and then she travels some more. And you know, I kind of admire that dedication to the thing that called her. Jessica moved back to the United States and got a new job… But it only lasted a year before she quit for the last time. “And I haven’t worked for anyone ever since!”

“I’ve never burned a work bridge,” Jessica explained. She was always a very hard worker and gave each professional opportunity the full scope of her efforts and attention, which meant she could quit, travel for months on end, and then be welcomed back into the workforce because her reputation as a hard worker held up.

“The most important thing for me is my freedom. So that’s what I’m always chasing. My freedom of time. Location independence. I love that I can wake up every single day and do exactly what I want to do, and that’s what I’ve worked for the last 10 years. That’s been the focus and I’ve set my life up so that I can have that opportunity.”

Why She Set the Goal

It wasn’t until 2017 when Jessica had a moment: What do I want to do with my life? Her life was already incredible but as she sat in Bali with a friend thinking about the impact she wanted to leave on the earth, she felt she hadn’t done anything of note.

Jessica had already been to 60 countries (Indonesia was her 60th). “But I had no idea there was a country counting community. And at the time, only 150 people in the world had [visited all 195 countries]. And they were mostly Northern European men.”

When she found out there was no documented Black woman who had completed the 195 country journey, she said to herself, “Don’t mind if I do!” And she just started.

“I didn’t make a plan. I just started. Of course, there were some roadblocks, but I didn’t know how much it was cost. I didn’t have a budget. I just wanted to do it and so I went and did it. So many times when people want to start something, they get caught in the planning stage… If you want to start, just do it.”

In her journey to reach 195 countries, she spent the night in all of them but 11, and in those few she stayed to have a meal and visit with locals, ensuring she had a significant experience in each place she landed.

Digital Nomad Lifestyle

Jessica traveled and worked remotely for the UN for a big chunk of time, but when she started her quest to reach all 195 countries, she was working for herself. She had launched a retreat business called Jet Black that planned and hosted group trips to Africa and other areas. So no matter where she was, she needed to be able to work.

Her strategy for battling time zones and balancing her desire to explore with her need to work, she’d get up early and work for a few hours before breakfast. The afternoon was hers to explore and experience whichever country she was calling home at the time.

Working remotely in foreign countries also meant that access to WiFi or cell service was less than consistent. Jessica swears by her TMobile hotspot (not sponsored at all!) but their service is available in over 200 countries and territories, which meant she was connected everywhere.

But the lifestyle requires sacrifices. Jessica’s personal relationships are difficult. She’s missed weddings and funerals and birthdays. “I’ve had to be selfish during this journey. It takes a lot out of you.” The next year is dedicated to rebuilding and growing her personal relationships.

How to Get Remote Work Perks

Jessica was able to negotiate remote work opportunities and her secret for working this into your own employment is simple: “You have to show your value.”

A remote worker has to prove that they’re just a valuable to a company even when they’re not in the office. Your worth to the company has to be so clear that the company would consider a remote work situation to keep you around.

Secondly, start small. Ask for one work from home day per month. And work your butt off while you’re at home. Bump it to two, advance to a week, and maybe even a month. When you’re valued as an employee and still deliver on your work responsibilities when you’re not holding up the walls of your cubicle every day, your employer will be more likely to consider your remote work idea.

Monetize Your Skills

“I do not get paid to travel. I have not figured out how that works. If any other travel influencers want to share that cheat code with me…” Jessica laughed.

Jessica was clear on her feelings here and said that it’s not about chasing the idea that you can get paid to travel. Out of the 195 countries, only ONE of her visits was paid for by a tourism board. Instead of looking for the influencer-style income, Jessica suggests, “It’s about monetizing your skills.”

If social media is your strength, freelance as a remote social media manager. Copywriting, video editing, photo editing… There are so many skills you can offer that don’t require you to be in an office. You can be a remote traveling digital nomad if you monetize your skills.

More from this Episode

If you want to hear more about Jessica’s journey, press play right now. Hear Jessica’s call to all women to release the fear of solo travel and her advice to make the trip happen as a solo traveler. Plus, I ask her a question she hates (oops!) but she tells me her top five favorite countries at the moment. You can find her online at The Catch Me If You Can.


We Love Our Goal Digger Sponsors

Get 2 months of Skillshare Free

Get your first pair of shoes from ShoeDazzle for 75% off

Leave a Reply

Your email address will not be published. Required fields are marked *

  1. […] first heard her speak on the Goal Digger podcast, but when I searched her name using the podcast search feature, I found several Black podcasters […]


The Latest From the Goal Digger Podcast

BINGE listens


Before you get any further... Hi! I'm Jenna Kutcher!

A small town Minnesota photographer, podcaster, educator and puppy rescuer, my happiest days are spent behind my computer screen sharing my secrets with the world. I'm glad you're here.

I’m an expert at online marketing, a nerd when it comes to the numbers, and my obsession is teaching others how to make a living doing what they love (without it taking over their life). 

hey there!


What do you want to read today?

Except instead of a video game, this is you IRL. Let’s get laser focused on setting your goals for this month, year, and beyond so I can hand over resources specific to how YOU want to grow!

Take The Quiz!



free downloads show


Free downloads to elevate your game.

FREE challenge



Screw the junk mail, I'm bringing "real" right to your inbox. Deep encouragement, tough questions, needle-moving challenges, and smart strategies to help you make your dream work. You in?

great idea alert!

Hey, Let's Be Pen Pals!

    © JENNA KUTCHER 2024


    |    SITE CREDIT

    |    GET IN TOUCH

    |    Legal