In this episode, we have a very honest, very open conversation with Derek from Wandering Earl on his 20+ years of digital nomad experience.
21 years to be exact. Of nonstop travel — a shock even to himself. Let’s start back at the beginning…
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How did this journey start for you? What are the “qualifications” of your digital nomad experience?
Right after I graduated from college, I was ready to be a sports agent. It’s what I had studied for. But I just wanted to take three months off to travel to SE Asia. I had about $1,500 to my name, and I went. That was Christmas day, 1999.
About a week later, I quickly realized that I didn’t want to go home… No, I wanted to keep traveling forever. Didn’t think it was a possibility but I did keep going and it’s been pretty much forever since then. Along the way, I ended up doing all sorts of things: Teaching English in Thailand, working on cruise ships, and then working online — creating ebooks & starting a travel blog (luckily when there weren’t too many of them).
And I managed to turn that blog into something so that by 2013, I could start an offshoot tour company. Lots of my readers were very interested in traveling with me or like me, so I created this company that runs ~20 tours per year in 15 different countries.
What’s changed in the travel blogging industry over the past decade-plus?
The biggest difference in the industry: Before 2010, it wasn’t a business. It was literally a way to share experiences, connect with other people. We didn’t really know it was a way to earn money in any way. It was much more honest, with a communal, helpful feel.
Slowly, opportunities to make money came here and there — offering things readers might want & helping them in some direct way.
Now, nobody starts a blog for that reason. Everyone’s looking to monetize. I even know of travel bloggers who don’t travel! Because now, you can do all the research online and you can write the posts to get to the top Google search. They’re not made to offer people value, but to offer search engines value. That right there’s the biggest difference: The focus is purely business.
It’s a bit sad: Some of the charm is gone. Because people aren’t writing about the cool activity they did or the transformative digital nomad experience they went through… Unless it brings clicks.
How about you? Have you lost some charm & honesty with your blog?
Yeah, it totally slid a bit! But that’s why I started my newsletter.
Now, I spend much less time on my blog. For that very reason: I want to maintain a connection with people. And I realize the newsletter is the way to do that. These are the people who signed up and want to hear from me. I don’t have to worry about Google when I send those.
Nearly all of my energy goes there nowadays!
What are some of the big life changes you’ve experienced since we last spoke 7, 8 years ago?
A major one was definitely adopting Matcha, a rescue kitten, this past year while stuck in Bali during the pandemic. And of course, now I’m in a relationship.
But bigger picture: As I’ve gotten older, my travel style has changed significantly. It’s less and less of that constant moving and bouncing around. That stuff just takes a toll on you — I’ve done it for so long now that you can get tired of it. So I do everything in a slower way now. And a more comfortable way.
The rest would be the business aspects, which now dictate a fairly large part of my life. (See below).
Over 20 years, how have you excelled at this apparent paradox: Adding attachments while staying flexible on the road?
For a while, you can definitely travel around without any attachments. That lets you meet people, have adventures, get as much as you can from that. And then realize that “okay, this was an amazing experience but everyone’s going their separate ways. I’ll probably never see them again.” You move on and yeah, you can do that for quite a while.
It can get tricky because it’s pretty common to eventually get attached to people. Eventually, you start to miss community and deeper attachments.
But it all comes down to paying attention to yourself. I shifted my travel style because I started checking in with myself and asking: What am I missing right now? And one of the big ones was that sense of community and deeper connection.
Once I realized that, I made necessary adjustments to my life. Now, for instance, I’m in Playa del Carmen where a lot of my friends are situated. And eventually, once you feel like an attachment is fulfilled, you can move on to the next digital nomad experience.
Knowing when your attachments are fulfilled — it’s a matter of paying attention to yourself and your changing need for attachment.
To bring it back to Matcha — what’s your strategy for keeping an attachment like a pet?
We found the cat in bad shape in the jungle, only five days old. Took her to the vet, who said she probably won’t live. But we tried, and she lived!
So when it was time to leave Bali (not the best place for animals), we basically decided to help this cat out of Bali. And now she’s still with us; it wasn’t too much of a thought process.
We just wanted to make sure this kitten has a good, safe life. That meant taking her out of Bali… And now we’re settled here in Mexico. But honestly: I will probably have to make a decision with Matcha once business starts up again and I get back to traveling more consistently.
How would you compare the nomadic lifestyle back in 2013 (when hype was starting) to now (or, at least, pre-Covid 2019)?
Macro level: It looks like there are a ton more people living the digital nomadic experience and that it’s become this huge thing. But if you look a bit closer, that’s not actually the case.
There’s not a huge amount of people who want to live an actual nomadic lifestyle. When people referred to the nomadic lifestyle back then, it was mostly about people who actually wanted to bounce around the world and gain some great travel experiences, mixed in with the freedom to work online.
If you look at 2019, though, most “digital nomads” are actually just living in one place. They live in Lisbon. In Medellin. In Bali. And maybe they take some short trips here and there, but most people actually stay in one place. Because it’s not so much about the nomadic lifestyle it is being able to live somewhere else where other similar people are living.
So the main difference: The travel component has taken a backseat to just living in a different, cheaper place. Not so much a real nomadic lifestyle.
A better term is a remote worker for these kinds of people. In my mind “nomad” is more about bouncing from place to place.
We’ve talked about my startup journey; could you elaborate on yours?
My first startup was called Plantsify. Note: A lot of my project ideas come from the idea that blogs won’t be around forever. I have this constant thought of “what will it turn into next?”
Back then, my business partner and I envisioned that people were coming to travel blogs for reliable travel advice. So we created a platform where you would have expert travelers explaining where they’ve been and what kinds of travel they’re actually experts in. And then users could actually book sessions with them for a consultation to get direct advice.
Seemed like a good idea, but it came right as travel blogs took off. And in the end, it turned out that people didn’t want to pay for this advice because they could search for it elsewhere for free.
We did have a solid base of users, but most people turned away and that was ultimately why we closed it.
My current endeavors:
- The Wandering Earl Tour Company. Started it in 2013, bit of a hiatus this year of course, but next year should be back in action!
- Remote Club. This is a cool project, m to help this new wave of remote workers. Idea is to help them decide where to go, how much it will cost, and how to find apartments and communities. It’s sort of like a starter kit for potential destination cities — all the details & resources to make informed decisions and get settled easily.
Talking about community, what are some tips for the social mindset while on the road?
First, it’s needed. Connections are a necessary thing that many of us feed off of. Because you’re constantly in different places, surrounded by unfamiliarity. So one thing you can have as a foundation is people that you can connect with.
Bouncing around solo for years will get pretty lonely pretty fast… And you’ll miss that social connection.
The amazing thing now is that there’s barely a city in the world without some weekly meetup or event that you can attend to instantly meet people. Now that more people are doing this, more people are meeting other people in the same boat. It’s never been easier, even if you’re a super-introvert. You just have to show up at a single meetup and it usually takes off from there.
But also, if community is important to you, it makes sense to aim for hubs where lots of people go. I get emails all the time like “Hey, I’ve been traveling for 7 months now. I’m kinda burnt out, I don’t know, should I go home?” And always, when I talk to them some more, it comes down a lack of connections — they’ve just been on their own too long. And I always say: Just go to the closest hub and spend a month there!
Let’s dig deeper: How are you so good at socializing while traveling? Is it natural or do you have to push yourself?
It honestly comes down to one very simple thing: When I was celebrating the millennium, on December 31st, 1999, I was in Angkor Wat, Cambodia. That’s the night I realized I really wanted to travel forever.
And the thing is, I was in the jungle, celebrating in front of these incredible temples… But that wasn’t why I wanted to travel forever. The only reason that came into my head was: Wow, I’ve only been in Asia for a week, and if I look at everyone I’ve met — locals, travelers, whoever — I’ve had so many interesting conversations and connections. That’s the value of travel, and that’s what I want to keep doing.
So if I’m going to travel forever just to see all the sights of the world and all the tourist hot spots, I’m going to get sick of that very quickly. The social connections are what brought me down this digital nomad experience, and I remind myself of this all the time. Connecting with all sorts of different people — that’s how you get a better education of the world and a better understanding of yourself. And that’s what it’s all about for me.
Yes, I travel to see sights and places of course, but it always come down to people in the end — that’s been the core for my past 21 years.
We had an episode about the term “meta nomad” — how do you balance the “meta” work life with your nomadic pursuit?
One of the realizations I made is that most of the time that I’m working… I’m actually not doing anything. Because you do get addicted to that meta-reality and you end up thinking that you’re doing useful work when you’re actually not.
That was a big step: Realizing that if I really focus, I could really get it all done in two hours instead of, say, six hours. And I could spend the rest of my time on things I actually enjoy away from work. Once that really clicked, I forced myself to work less and get more out of that allotted time.
Even if I don’t finish my task, I still stop and keep the time boundary. And if there are consequences of not finishing my work in those two hours, I let there be consequences! Because then the next time, I guarantee I’ll get more done in those two hours.
So now, I’ve gotten to the point where I can get my work done efficiently early in the day and spend the rest of my day away from the meta world. And if I need to, I’ll do more work in the evening. But I keep the pre-set boundaries.
Overall, it helps to focus and remember why you’re doing these things in the first place. You don’t have to be traveling and adventuring 24/7, but part of the reason you’re being nomadic is so that you can go and do things that you couldn’t do back home.
I think that’s important to remember. And even if you look at a calendar and say, “Okay — there are four things I really want to do here,” you can make a goal to do one each week. The more of this stuff you do away from work, the more you get motivated to get that work done in a shorter period of time.
It takes practice, but over time, you can get that balance to shift into a healthy work/life/meta-nomad balance.
How about the fun element of traveling. Would you say there is less “magic” now than there was early on?
Yes and no. The eyes-wide-open magic when I first started traveling — I don’t have that now. After doing it for 20 years, it’s become more normal, naturally.
For instance: Last year, I went to East Timor — I mean, that’s crazy, right? But I definitely didn’t have the same wonder that I did in Cambodia back in 1999. That magic is gone… In a way.
However, I realized over time: The magic is not in the destination. The magic is within ourselves. So it’s about what I look for. And now, when I go to a place, I focus on what I want to get out of that experience. That’s where the magic comes from.
I might not be running around like a kid all excited anymore, but there’s still a kind of magic. In East Timor, the magic was finding a local person to drive us around and seeing exclusively local places. Interacting with local people. And getting a feel for a regular town, a village, a market — anything totally normal. We got a real experience of what it’s like there, and that’s a type of magic for me.
Sure, we could’ve gone to their famous snorkeling island or what have you, but it wouldn’t have been the same. That’s not what we wanted to get out of it.
With time, you have to adjust your travels to make them create the magic you’re genuinely looking for.
Curious about Wandering Earl & his 20 years of traveling? Check out his website or email him here. And let us know your thoughts on this conversation below!
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