This is the first of a series of interviews with digital nomads about their lives and lessons. The goal is to help anyone interested in making money remotely, living a better life, traveling, and/or financially retiring at a young age.
For the purposes of this interview, a digital nomad is defined as someone who makes money in a remote, location independent way while wandering the world (and has been doing it for at least 6 months).
If you’d like to be interviewed, you can learn more here!
Table of Contents
- 1 How has traveling the world changed your life?
- 2 How has nomading changed your views on conformity, societal pressures, and building a custom life path?
- 3 What were your biggest concerns right before you started traveling? And how were those concerns appeased or not appeased when you started traveling?
- 4 If you only had a few minutes to live, what are the most important life lessons that you would share with the world?
- 5 What’s your philosophy about finding meaning and purpose in life?
- 6 What’s your favorite book and why?
- 7 When did you start nomading and what inspired you to start traveling the world?
- 8 What advice would you give to someone who’s thinking about digital nomading or who’s about to digital nomad?
- 9 What is your background and what do you do for work?
- 10 Where are you currently living and would you recommend it to other people working online & traveling? Why/why not?
- 11 What is one of your favorite travel stories/experiences?
- 12 What are your 2-3 favorite places where you’ve lived/traveled to and why?
- 13 What are the top places on your list that you haven’t traveled to yet?
- 14 What is your nomadic traveling style and how/why has it evolved since you started traveling?
- 15 Any tips for other nomads on how to best meet people while traveling?
- 16 What’s the best advice that you would give to potential entrepreneurs?
- 17 What are some of your biggest recent business learnings that other people can learn from?
- 18 Who are your favorite thought leaders in your field?
- 19 What small change has made a big difference in your life?
- 20 What’s the best purchase you’ve made under $100 in the last 12 months?
- 21 What software or app that you pay for has added the most value to your life?
- 22 What other paid or unpaid software and apps help power your life?
- 23 What’s the most difficult thing you’ve been through in your life and how has it shaped you into who you are today?
- 24 How can people learn more about you and your work?
How has traveling the world changed your life?
Too much to share in one quick answer! Traveling has:
- Made me much more easy-going
- Helped me to find my purpose in life
- Helped me to figure out what makes me happy
- Made it possible to reach financial retirement at a young age because of the low cost of living
- Taught me that money is best used as a tool to create freedom and purpose, not to acquire things
- Become more grateful
- Appreciate and love humanity
- More confident in myself
- Able to live my dream life
How has nomading changed your views on conformity, societal pressures, and building a custom life path?
One of the most underrated aspects of living abroad is that by leaving your home society and being a guest in every society that you live in, you aren’t bound to the rules and pressures of any society. I refer to this concept as “falling off the bell curve” because it enabled me to focus on figuring out who I am and how I want to live my life free from any outside pressures.
I didn’t fully grasp how much conformity affected my life and state of mind until I escaped and had space to think independently. Traveling gave me the breathing room to decode and unpack a lot of the societal programming in my brain about money, happiness, consumerism, and meaning.
This freedom helped me to rebuild myself and create a custom-built life path based upon what’s best for me. And after spending years going on this journey in isolation, I’m excited to share my learnings!
What were your biggest concerns right before you started traveling? And how were those concerns appeased or not appeased when you started traveling?
My fear of the unknown was big. I had a one-way flight from NYC to Bali and I just didn’t really know what to expect, what the people would be like, or how I would make friends.
Once I got there, all of those fears dissipated within a week to a month. Leaping into the unknown feels scary, but the reality of living on a beach and paradise is unbeatable once it becomes a known quantity. The people were super friendly, and I made a bunch of friends through Dojo, the local co-working space.
Like with anything, the more you travel, the easier it becomes and the more comfortable you become doing it.
I did a full video about this here.
Here are my main points:
- Life is short, figure out what you want to do in life and go do it
- Going for it and not going for it in life is a binary thing.
- Learn from the experiences knowledge of others, but don’t take advice.
- Your hardest moments in life give you the most strength.
- Don’t chase money, chase happiness and meaning
- Working online and living abroad is the fastest shortcut to freedom and happiness
- When analyzing risk, think about the worst-case scenario and block out the voices of others
- Your possibilities in life are limitless once you understand you can learn anything and meet anyone via the internet
- Be friendly, be kind and be grateful because the world needs it
- Read the alchemist and listen to the philosopher Brian Johnson
What’s your philosophy about finding meaning and purpose in life?
Ask yourself the question, “If I died today, why would my life matter?” And if you aren’t satisfied with your answer then make changes in your life until you’re satisfied with your answer.
Don’t wait until later in life to chase meaning and purpose because life is short and it can be taken away from you at any moment. The time to optimize your life for purpose is now.
What’s your favorite book and why?
The Alchemist. So many powerful life lessons packed into that short story. I re-read the book every 6-12 months and any time I’m going through a transitional moment in my life.
Helped teach me to figure out what you want out of life, put on your blinders, and go for it. It gets my strongest possible endorsement for anyone interested in living an extraordinary life.
When did you start nomading and what inspired you to start traveling the world?
I originally started nomading in June of 2015 when I wandered around the U.S. and Canada launching new markets for DoorDash. But my journey of traveling while building online businesses and being location independent started in March of 2017.
I started traveling the world because I had just quit back to back jobs in Silicon Valley and I needed to live cheaply while figuring out how to make enough money to never get a job again.
Living abroad seemed a lot more fun and interesting than living at my parents’ house (no offense mom and dad!). And what was supposed to be a 3-6 month trip has turned into a life of wandering around!
I’ve spent the last ~4 years living in 16 countries across North America, Europe, South America, the Caribbean, Australia, and Asia.
What advice would you give to someone who’s thinking about digital nomading or who’s about to digital nomad?
Give it a shot! I always try to think through big decisions by focusing on 1) what do I think is best? 2) what is the worst case scenario if I do this?
After I quit my job and started traveling, the worst case scenario was that I would go home and get a new job. If the worst case scenario isn’t bad, then I highly recommend trying this out.
What is your background and what do you do for work?
My background is as an entrepreneurial and digital generalist. Before traveling, I spent about a decade working for and starting tech and internet-driven businesses.
I currently run a remote, impact-focused startup lab called Nomad Impact Ventures. My work is mostly focused on building content sites to create global change on key issues and to help people improve their lives.
My impact-focused work has reached more than a billion people and has been featured by most major media outlets and many governments including the New York Times, the Wall Street Journal, CNN, BBC, and the U.S. & U.K. Governments.
For most of 2017-2019 (my first few years of traveling), I focused on reaching financial retirement so that I could focus my time on high impact endeavors. To accomplish this, I started three different content sites that now collectively reach more than a million readers annually and I scaled a social media agency from inception to $200k+ monthly recurring revenue.
Where are you currently living and would you recommend it to other people working online & traveling? Why/why not?
I’m currently in Barbados! 🇧🇧 I highly recommend Barbados to anyone who’s looking for an island beach destination during COVID-19. While it’s only ~20-25% cheaper than living in the U.S., Barbados has almost no COVID which means that bars, nightlife and other social activities are all open.
There are lots of things to love: the people here are friendly, the weather is warm, the food is good, there’s solid surfing, and there’s a small community of other nomads.
If you’re looking for a winter escape from the U.S. or Canada, I highly recommend it here! P.S. I’ve been making content about Barbados on my YouTube channel if you’re interested in learning more.
What is one of your favorite travel stories/experiences?
I spent two months living in Taiwan in late 2017 and at the time I was recovering from a partially torn pec muscle. I tried to order some resistance bands from the biggest e-commerce store but I couldn’t get the order to go through.
Every time I tried to check out, it would give me an error message in Mandarin that I wasn’t able to translate. After 20 minutes of failing to place an order, I walked to the nearest cafe, found two girls in their early 20s, and asked them if they could translate the error message for me.
They giggled and told me that I needed to write a name in Mandarin. So they helped me come up with a name and we placed the order! 🙂
Fast forward to the next day, the delivery driver called me on my cell phone and tried to talk to me in Mandarin (which I speak about two words of). After a minute of wondering what the hell I was going to do, I ran across the street from my apartment into a restaurant and asked the hostess if she could help me get my package delivered.
She was confused but took my phone and spent a few minutes on the phone with the driver before letting me know that he would be in front of my apartment in fifteen minutes. And fifteen minutes later I had my exercise bands :).
This story is representative of two consistent themes during my travels:
- Humans are generally very kind and helpful, especially if you’re a foreigner who needs help
- Living or traveling in places where you don’t speak the local language is much easier than most people realize, you just have to be willing to ask for help
What are your 2-3 favorite places where you’ve lived/traveled to and why?
My favorite place in the world is Bali, Indonesia. The combination of cheap living, delicious food, warm weather, great surfing, lots of adventures, beautiful & friendly people, diverse and vibrant expat community, scooter life, and so many other things makes this unbeatable for me right now.
My other favorite place is Taipei, Taiwan. I love the kind people, great food, and the overall vibe there.
If you don’t need to be near the beach or on an island, I highly recommend Medellin, Colombia as that’s definitely my favorite non-island location.
What are the top places on your list that you haven’t traveled to yet?
My shortlist of places to visit right now is all surf spots: Sri Lanka; the Philippines; Florianopolis, Brazil; Huanchaco, Peru; Hawaii; Puerto Rico.
What is your nomadic traveling style and how/why has it evolved since you started traveling?
I changed places every 5-8 weeks for my first 18 months of traveling. Once I had visited most of the places on my international list, I slowed way down and started spending more time in places that I loved.
Traveling quickly is fantastic but it can get tiring and make it difficult to be productive and build deep relationships.
For the last two years, I’ve been spending 3-5 months in any given place before moving on. After COVID-19, I plan to spend 8-9 months out of the year in Bali and I’ll wander around the world for the remaining months!
Any tips for other nomads on how to best meet people while traveling?
Local digital nomad and expat Facebook groups (i.e. Barbados Digital Nomads) are one of the easiest ways to get connected to other travelers. You can post mentioning that you’re new, are looking to meet new people, and ask if anyone wants to get a drink. Once you meet one friendly person, they can help you meet lots of other people as well.
Dating apps are great if you’re single.
I’ve written about some other tips in this post as well!
What’s the best advice that you would give to potential entrepreneurs?
The best way to learn how to start a company is by starting a company. Don’t wait for the perfect moment to start a company, just get going.
What are some of your biggest recent business learnings that other people can learn from?
- The power of videos with storytelling: the content that has gone most viral during COVID has consistently been storytelling videos from credible (or seemingly credible) people. The formula is fairly simple at surface level (establish credibility > share a powerful firsthand story > make a case for whatever you’re trying to convince someone of). I’m heavily shifting my focus to video content as a result of this learning.
- Things don’t have to be perfect to be massively successful: I used to run the special projects group at DoorDash and I left back in mid-2016 because things internally were a disaster and I was convinced that the company was fucked. Fast forward to today, the company went public at ~80x the valuation of when I left. Long story short, a million things can go wrong and you can still build a massively successful company so focus on the long-term and don’t worry too much about the short-term challenges.
Who are your favorite thought leaders in your field?
What small change has made a big difference in your life?
Turning off most phone notifications, turning off all sound/vibration notifications on my phone (except calendar notifications), and running no meeting/no call companies. By living life with mostly no schedule and without any interruptions, it has increased my creativity by 1,000x and helped me to enjoy life a lot more.
What’s the best purchase you’ve made under $100 in the last 12 months?
A massage gun! It wasn’t less than $100 when I bought it but you can now buy them for under $100. Has helped me with chronic hip and shoulder issues.
This isn’t the model that I bought but here’s one under $100 🙂
What software or app that you pay for has added the most value to your life?
Daywise. It helps me to turn off tons of notifications on my phone and live distraction-free.
What other paid or unpaid software and apps help power your life?
Notion, Evernote, Headspace and Spotify are a few that come to mind!
What’s the most difficult thing you’ve been through in your life and how has it shaped you into who you are today?
Battling depression during my high school years is the most challenging thing I’ve faced in my lifetime by far. You can read the full story and lessons here.