Millennial Travel Podcast

Becoming a Digital Nomad: How to Travel the World, Work Online, and Have a Life You Love

Matt Wilson
January 16, 2024
“Velkomin á Íslandi” 

I heard as I pried my eyes open getting off the red eye flight.

Beautiful blonde Icelandic women with farm working physiques gracefully bullied their way to the overhead compartment.   

My mountain guide met me at the terminal. “Hello I am Siggurdur Bjarni Svienson.” <insert long pause> “But you can call me Siggi" he said with a slight sense of dry Icelandic humor.

The sun was barely up. A thick mist of dense clouds rolled in from the North Atlantic. The ground was black, covered with sharp lava rock. Not a tree in sight.

Where the fuck am I? I wondered.

I started to feel bad that humans even attempted to live here.

We wound our way down the Icelandic coastline to the capital city of Reykjavik where 230,000 of the 330,000 inhabitants of this bleak terrain decided to call home.

Siggi dropped me at my hostel and said he’d return that evening.

I was on my own.

Becoming a Digital Nomad 

What was the first thing I did on my trip to Iceland that Sunday morning at 8 am?  

Answered emails.

I shit you not.

I was addicted.

This is incredibly embarrassing thinking back at it. Do you know how many people in that inbox truly did not matter?

At the time my Co-founder Jared O’Toole and I were running a successful media site for young entrepreneurs called It was near the peak of our traffic numbers, at over 500,000 unique visitors per month…we had boatloads of fans from India, Nigeria, Bangladesh, and of course all over the United States, Canada, Australia, and the UK.

God, we thought we were important.

Note: if you want to see hilarious pictures of Jared and I on jumbotrons in Time Square, ringing the closing bell at NASDAQ, or being invited to yap about the importance of small business on Fox Business, take a look at the article announcing that Under30CEO was acquired.

How to travel the world and never really have a chance to enjoy it

Okay, I’m joking. But not really.

Everyone wants to be a digital nomad these days… but not so long ago, co-working spaces like WeWork were not a thing, hostels didn’t have conference rooms, and you could’ve actually found a seat at a coffee shop in Austin, Texas.

The reality is, being a digital nomad is fucking awesome. It’s why it seems that all the cool kids are doing it.

And therein, lies the problem: the cool kids.

Yup, I am sad to say I was one of them.

Addicted to email. Caffeine. And worst of all, stress.

The rest of this post is going to be devoted to strategies on…

How to break free from your desk, travel the world, and not stress yourself out 


I’ll be honest, when I hear someone describe themselves a “digital nomad” I usually cringe. Call me a seasoned gringo, but the “cool kids club” is exactly why I packed up and left New York. I’m not trying to hang out with a bunch of stressed out people talking about marketing, complaining about the wifi here in Costa Rica.

If you really want to enjoy the “pura vida” as we say, you’ll first have to get a handle on your travel schedule. The first rule of thumb is don’t overdo it.

In upcoming posts, you’ll hear me talk about how stressed out I was my first time to Bali, traveling around the island until I found a Starbucks because I had to hit a deadline. Backpacking and hitting deadlines really doesn’t work. You shouldn’t try to travel South America while taking on new web design projects. You need to find somewhere you like and develop a routine so you can be in a higher state of flow, complete your work, and then go have fun.

Choose your City

As a general rule, cities have better wifi than rural locations. This is bad news for me, as I prefer mountain hideaways and surf towns. These places also have worse 3G and 4G cell service, which you’ll need as backup when the wifi goes down. If you want some cities that are close to natural wonders, think Medellin, Colombia, or Chiang Mai, Thailand. Nomad List is an incredible resource for comparing cost of living and intel on how good the wifi is.

Choose your Dwelling

This for me is one of the most fun parts of living in places where the dollar goes far. I’ve lived in $300/month local spots in Costa Rica to massive villas with a pool and security. My current setup is a private four bedroom house in the jungle, and luckily for me, the lower level has a private entrance which I can Airbnb when I want. During tourist season I can easily pay my rent with the money earned on Airbnb and when friends, family, or business associates come to visit, they have plenty of space.  

Costa Rica is far from cheap however. Friends who live in Thailand or Bali can afford places that are absolutely palatial.  

I realize now that I’m making joining the digital nomad “cool kids club” sound a little too easy. I want you to know that it’s often a pain in the ass to find places to live as a digital nomad. Remember, in the developing world, a quick google search for “apartamentos Costa Rica” won’t help much.  

Some quick tips:

  • Find local expat groups like "Expatriates in Nicaragua" or "Gringos in Medellin" where there are often listings
  • Make a local connection. In Cusco, we found the Under30Experiences’ staff house through the brother of the owner of the hotel where we stay. All the listings online were long term leases only.
  • Ask around. In Bali, Luz, my girlfriend and Under30Experiences’ Yoga Teacher, found an amazing place to stay right next to the Yoga Barn for just $20 night just by asking her driver.
  • Avoid tourist areas, as people make more money on nightly rentals than they do renting their apartment per month. Prices of monthly apartments in places like Barcelona become inflated.

Pay Attention to Quality of Life

If your job is to work from a computer you need to think about how you can best get into flow state without the interruptions. Remember-- you want to get your work done and then go explore, and get to know a place. You won’t want to stay in a hostel for very long as they usually aren’t conducive to work. There are exceptions like Selina’s across Panama, Colombia, and Costa Rica that offer built in co-working spaces.

When I did a stint in Barcelona, I found a place with a kitchen, connected to a gym, down the street from a great grocery store, with great internet, and lots of cafe’s with wifi nearby just in case I needed a backup place to work. These are the things that make me productive.  

Other things that digital nomads’ love that are usually affordable and make them more productive include maid service, access to transportation and again, co-working. In Paris I lived a block from the metro and could walk to one of their Anti-cafe concepts where I paid by the hour for co-working.


The longer you stay in a place, the better you will understand where to get the best internet connection. Here in Costa Rica, I struggled with the wifi for years until I got it figured out. Once I discovered that I could have a 4G Personal Hotspot through my cell phone service with Movistar my life changed. When the wifi is down, I simply put on my hotspot.

Since I’ve been living here for a while, I know to immediately call a technician when the wifi is down. It helps I’m fluent in Spanish now. Me trying to get the wifi working in French put me back down to tourist status.  

I even have friends who have two internet service providers at their house in Costa Rica just in case one goes down. Make friends with the wait staff at your favorite cafes so they will reset the router for you. Select a workspace next door to a restaurant with good wifi. The Under30Experiences Costa Rica office always has a backup… thank you Sancho’s!

When selecting a place to set up shop, check out Nomad List’s internet rankings before you go, and once you get to a place use to see at how many MBPS you are working with. For a general workday including Skype audio calls and podcast recordings 5-10 MBPS works fine for me.

Bring on the Fun

At the end of the day it all comes down to designing the life you want. I know it’s tempting to try and see the entire world, but you’ll need to get the backpacking and moving around out of your system until you are exhausted. Then, go back to a place you really loved and spend more time there. My initial strategy of traveling every five days was disastrous. I worked Monday - Friday, packed up, and then traveled to my next destination over the weekend. This led me to quick burnout as I describe in this throwback “Confessions of a 26 year old Entrepreneur.”

Finally, I went back to the place that had the most to offer me. I wanted to learn Spanish, surf, practice yoga, and live in nature. Select a place that’s right for you during this point in your life. Realize that life on the road is lonely, so settling into a place will help you make connections and become part of a community. I happen to love small town life, where I know everyone at my local bar. Other people can’t stand it.  

Choose what’s right for you and make sure you find yourself in a place where you can continue to learn and grow as a human.

That’s the point of travel.

Pura vida.


Check out the podcast episode here:


Listen in Now, and start your journey toward having the life you want!

You can get this episode directly to your iPhone on iTunes, your Android on Stitcher, or on Soundcloud.

Matt Wilson
Matt Wilson is Co-founder of Under30Experiences and Author of The Millennial Travel Guidebook: Escape More, Spend Less, & Make Travel a Priority in Your Life. He is host of the Live Different Podcast, Millennial Travel Podcast, and formerly Co-founder of He is committed to helping people live more adventurous lives.


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