From Bartender to Digital Entrepreneur Wandering the World (Joe Lannen’s Story)

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This is the latest interview in a series featuring digital nomads talking about their lives and lessons (click here if you want to be interviewed). The goal is to help demystify the process of making money online, wandering the world, and living an unconventional life!

I met Joe in Bali, Indonesia back in 2017, and since then we’ve run into each other in coworking spaces and coffee shops all over the world.

Joe’s laid back attitude and love for life really shine through in this interview :). His favorite travel story is an absolute must-read and epitomizes the wild and adventurous life of a traveler!

His advice to nomads is simple but profound: “Go for it, you’ll figure it out if you prioritize and decide that you’re going to be the hardest working person you know.”

The biggest difference I’ve found between nomads who make it and those who don’t comes down to commitment and work ethic. His advice hits this nail on the head without any extra fluff.

Where are you originally from, when did you start nomading and what inspired you to start traveling the world?

I grew up in a couple of small towns in central Illinois called LaSalle and Spring Valley.

In 2012 I was living in San Diego, California in a 1 bedroom beach cottage 1 block from the beach (OB represent wooooot 🏄‍♂️🤙). I thought “man I could live here forever but it would be fun to drastically switch it up”.

So I moved to New York City for 2 years, then sold most everything I own and left the US with 2 backpacks and a 1-way ticket to Thailand on January 5th, 2015.

What is one of your favorite travel stories/experiences?

I showed up in Wenzhou, China at the airport around 10 at night and my phone didn’t have connection, and nobody spoke English or Spanish, just had a hotel booked and the name of it written in Chinese. I didn’t have the Chinese language pack downloaded in Google Translate but managed a laughable convo through hand signal with some airport workers that I wanted to get a cab to get to my hotel.

I grab some Yuans from the atm and they help me get a cab outside. It was a small airport so there aren’t lines of yellow taxis waiting to pick you up… it was more like the girl working the desk yelled out into the air in Chinese, then some guy pulls up a couple minutes later in a beat up 90’s half rusted red sedan with missing a missing hubcap. Nice.

My instincts are like duuuude is this a smart idea? Then my “eh fuckit” side says let’s see what happens, and besides I don’t really have options at this point.

I get in and the back right side and the driver turns to me, cigarette in his mouth, ripped gray t-shirt and with wired eyes like a Chinese Johnny Depp in Fear and Loathing in Las Vegas, “get in” (but in Chinese). I’m like hah heyyyyyy what’s up man (show him my paper with the hotel name written), he looks for a few seconds then returns with a big smile and more Chinese, gives me the paper back and off we go.

I have no idea where I’m at or where I’m going, but at least guy seems friendly right?

He floors it, I look for my seatbelt, no seatbelt. Nice.

Within 30 seconds he offers me a cigarette (Chinese hospitality), I don’t smoke but eh sure man let’s go whatcha got. So here I am, 10 minutes after coming out the gate, in a beater car that’s clearly not a taxi, no seatbelt, smoking a cig with this random Chinese “taxi driver”.

Then dude cranks up the stereo, Chinese EDM. Woooo! haha we’re practically partying at this point – he’s flyin, we’re smokin cigs blastin Chinese techno seat dancin, he’s yellin out Chinese I’m talking in “Asian English” but nothing gettin through either way.

About 15 minutes later I recognize my hotel from the picture when I booked and the name on the side. Yes! Good on ye mate thank you.

He uses his hands and fingers to name the price, I think it was like 25 Yuan, I give him some cash + a few bills for the epic hospitality (and safe ride!), we fistbump and part ways.

What is your background and what do you do for work?

I’ve worked a lot of different jobs starting with delivering papers and corn detasseling as a teenager, then mostly bartending and tech in my 20’s, tech and entrepreneurship in my 30’s… the tech is what initially enabled the freedom of self employment.

For work, I own 2 businesses, an outdoor lifestyle brand called Tree Tribe and a web development agency called Speed Boostr.

Tree Tribe started as a passion project – I wanted to start a business that gave back to the Earth by planting trees. Speed Boostr started as an idea for a side project to try and dominate a niche… and also because I missed coding. 🤓

How has traveling the world changed your life?

Aw man, how can you even put it in words… it’s changed my life in the most epic way, gifted me with amazing experiences, opened my mind in new ways, introduced me to awesome people, and makes me feel like Earth is my neighborhood no matter where I’m at.

Where are you currently living and would you recommend it to other people working online & traveling? Why/why not?

Colombia. I’ve been based out of Medellin since 2016, but right now I’m bouncing around a bit to experience some other spots, currently in Bogota (a great city and my 2nd favorite city for skateboarding) and heading up to the coast later this month.

What are your 2-3 favorite places where you’ve lived/traveled to and why?

I like everywhere I’ve traveled, my personal favorites are Colombia and Canggu, Bali.

Colombia because I dig the people, the culture, the nature, the language… I just like it here, it’s my vibe.

Canggu (Bali, Indonesia) is just a great place where I like to hang for a couple months every year. It’s a cool beach town with world-class gyms / yoga / fitness, great parties and bars, a solid electronic music scene, awesome food, and my favorite place to reconnect with the digital nomad community. I hang more local style in Colombia, but when I’m in Canggu I’m in coworking spaces, going to meetups, and hangin with travelers from all over the world.

What were your biggest concerns right before you started traveling? And how were those concerns appeased or not appeased when you started traveling?

My main concern was income, at the time I was bartending nights and freelance web developer during the day. I didn’t have a regular income source, I knew I would have to hustle up to make it work.

What is your nomadic traveling style and how/why has it evolved since you started traveling?

I was pretty nomadic the first 2 years but now I like to have a home base and stay in places longer. I prefer to spend more time integrating with locals and being a part of the neighborhood.

What advice would you give to someone who’s thinking about digital nomading or who’s about to digital nomad?

Go for it, you’ll figure it out if you prioritize and decide that you’re going to be the hardest working person you know.

Any tips for other nomads on how to best meet people while traveling?

Work at coworking spaces, go to meetups, introduce yourself to people. It’s a friendly, supportive community and we all love meeting people and sharing ideas.

What’s the best advice that you would give to potential entrepreneurs?

Same as any other pursuit in life – Go for it and go hard, you’ll figure it out if you prioritize and decide that you’re going to be the hardest working person you know.

What small change has made a big difference in your life?

Not using an alarm clock or notifications on my phone. That 1 decision has made me 10x more effective in work and more free of mind throughout the day.

What software or app that you pay for has added the most value to your life? And are there any other paid or unpaid software and apps help power your life?

For business I really like Notion, it’s added huge value to my biz life. Outside of that, I gotta go with It’s an awesome internet radio app + has live sets + a lot of genres. I work to it, workout to it, party to it, chill to it.

What’s your favorite book and why?

The Alchemist because I read it in my 20’s during a soul searching phase and it unlocked a desire to travel and seek enlightenment through adventures and the people you meet in your journey.

If you only had a few minutes to live, what are the most important life lessons that you would share with the world?

Be kind, have fun, let loose!

What’s your philosophy about finding meaning and purpose in life?

I used to think deeply about this in my 20’s, now I just try to be present and enjoy the adventure of life 🤙

I've been building digital businesses, wandering the world, and writing about optimizing life for freedom since early 2017. My mission is to lower the barrier for people who want to live with more freedom: whether that be as an entrepreneur, a digital nomad, an early retiree, or just as someone who wants to live a happiness-driven life.