Interview: Derek Earl Baron, AKA Wandering Earl
On digital nomading, building a blog audience, travel gear, visiting Iraq, and a special travel offer for my readers
I spent most of 2016 living the digital nomad life– that is, traveling the world while working over the internet. Starting out in Thailand, I made my way through Southeast Asia, made briefs visits to India and Namibia before ending up in South America for a few months. Then as soon as I got home, I went right back to China and Japan for good measure.
I touched briefly on the subject of digital nomading in my previous interview with Amar Ghose. Today you’re going to hear from the guy who helped me begin my foray into nomading.
Derek Earl Baron, aka Wandering Earl, left home in 1999 shortly after graduating from university. He wanted to travel around SE Asia for 3 months before starting a career back in the US. Somehow, he never stopped traveling. Derek has now been traveling around the world for 23 years. He runs a popular travel blog and a tour company that organizes unique, small-group trips to some of his favorite countries.
The tour company has been in operation for over 10 years, helping travelers explore fascinating destinations in a style that you won't find with a typical group tour. He's been featured by publications such as Time Magazine and The New York Times and is frequently invited to speak at events and on podcasts in order to share the stories, insights and adventures from his life of travel.
In addition to his tours and a couple of e-books he sells, Derek offers travel advice via email in return for donations. That’s how I know him; in 2015, I asked him for advice and he helped me plan my itinerary for 2016.
Before we begin, here’s where to find Derek on the Internet
Peruse his tours at Wandering Earl Tours (read to the end for a special offer!)
His X profile (mostly inactive)
Instagram (way more active)
Interview with Wandering Earl
How did you first get started with the nomad life? Did you find it intimidating at first?
Back in 1999 I took a 3 month trip to SE Asia after graduating from university in the US. And about a week into that trip, I decided that I wanted to 'travel forever' instead. I had no idea what I was doing and really didn't believe I would travel for more than a year, but somehow, it kept going.
My main method was to speak with as many people as possible so that I could learn what others were doing to work, earn money and continue their travels. This led to all kinds of opportunities such as teaching English in Thailand, working as a Tour Manager on cruise ships and eventually, blogging. So for me, it wasn't really intimidating.
I made the decision to forgo my career and become a nomad very early on and I knew that once I made that decision, it was up to me to make sure I followed through and created the life I envisioned. It wasn't easy but with determination I kept pushing forward, seeking new opportunities that would allow me to progress in terms of finding ways to sustain myself.
What are your favorite destinations that you find yourself revisiting over and over?
I honestly love all destinations. To me, travel is about the interactions and connections with people that you make along the way, and rewarding interactions can be had in every single country on the planet. As a result, I don't find any reason not to love a destination!
With that said, I am drawn to certain countries. For me, the countries I return to most frequently these days are India, Romania and Iraq. They are all fascinating in their own ways and offer travelers an opportunity to meet incredible people in incredible surroundings. Those countries provide rewarding experiences one after the other for travelers that are open to going beyond the general highlights of mass tourism.
Iraq, I love it! I know that’s going to surprise a lot of people– I find most folks have concerns that certain parts of the world aren’t safe to travel in, and usually that’s overblown. But how do you figure out which places you truly need to steer clear of? Is that more a matter of researching places beforehand or reading the vibe once you’re there?
It's all about research, talking to local people in order to get an idea of the real situation and then examining the media stories with a mindset from 20+ years of travel and knowing how to actually interpret what I read or hear. Then, once I go myself, I can figure out the reality of the situation on a deeper level. But Iraq, for example, shocks people when they arrive.
A friend of mine just went two weeks ago, based on my recommendation, and he was also overwhelmed at how incredible and safe it was to travel around. It was nothing like he imagined at all. These are the things I've learned from my travels - most situations are not what we imagine when we imagine things based solely on media interpretation or attention-grabbing stories and social media posts.
You’ve sold me on Iraq–my veteran friends are going to love this. Which specific parts do you like?
The entire country! When I take groups there, we typically start in Baghdad, visit ancient Babylon, the incredible shrines in Najaf and Karbala and the Mesopotamia Marshes in the south near Basra. We then move north via Samarra and Hatra, spend time in Mosul, the villages of the Nineveh Plains and then finish in the Iraqi Kurdistan region, with time in Erbil and the incredible surrounding nature. Everywhere we go is an eye-opening and unbelievably rewarding experience!
What’s your favorite travel story?
It's probably the time I was kidnapped by inexperienced kidnappers in Dhaka, Bangladesh. After arriving late at night on a flight from Bangkok, I did what every guide book said not to do. I went outside the airport instead of waiting until sunrise. Once outside, I was surrounded by a group of taxi drivers who were arguing with each other about which one would take me into the city. When I finally chose one, I was taken to a taxi and before I knew it, I was pushed in the back seat and 4 of the drivers got in the taxi as well.
They told me they weren't taking me to the hotel I wanted to go to. They made me pay to fill up the car with gas and then they took me to a huge slum area where they led me into a dark building and put me in a small room with a disgusting bed and dirty bathroom full of cockroaches. They locked the door so I couldn't get out. The next day, they came to collect me and they demanded that I go to the ATM and take out money. So we went to an ATM and I typed in the wrong pin code and told them that it didn't work. For 2 days they kept taking me to ATMs and I kept doing the same thing with the incorrect pin number. They weren't armed and they didn't cause me any harm. But they simply continued demanding I give them money.
They took me to another building for the next night. Then, after our third trip around Dhaka without any luck at the ATMs, we arrived back at the building and they told me to go upstairs and get my stuff because they were moving me somewhere else. I went upstairs, grabbed my back (which these inexperienced kidnappers never took from me) and started to walk back down. I then looked at the end of the hallway and noticed an exit, with metal stairs leading to the street. I ran down the hall, walked down the steps and hopped into a rickshaw and told them to take me to the hotel I wanted to go to in the first place.
The kidnappers ended up with $200 USD, which was the only cash I had on me. Apart from that, they never took my camera or laptop or anything else. Luckily for me, they had no idea what they were doing!
I love that kidnapping story– I’ve certainly had my own experiences with incompetent criminals in my travels. Didn’t you also run into some kind of gunfight at the border around that time?
Yes, when I finally left Bangladesh and crossed the border overland into the Meghalaya state of India, I happened to cross during a gunfight between the two countries. It was a regular occurrence apparently where they would exchange some gunfire every now and then.
When I approached the completely empty border crossing, the local official did the necessary paperwork and the guard then blew his whistle, signaling for any gunfire to stop from both sides. Then they let me walk across the no man's land area of the border, which had no other people crossing, and continue on my way. After the kidnapping experience, this seemed remarkably normal at the time!
From John: There’s still more to the story, and it is well worth the read.
How do you stay fit and productive when you’re moving around all the time?
It's all about routine. There are many things I try to incorporate into my days, including meditation, stretching, a lot of walking, time on my laptop working and also time simply enjoying wherever I happen to be. I also focus on eating as healthy as possible and exercising whenever I can. It takes a lot of work as it's very easy to simply avoid work and avoid taking care of yourself and simply wander around all day trying to have fun. But since travel is a full time lifestyle for me, it's not always about the travel.
Like with most people, I need to work, exercise and focus on many aspects of life. The only difference is that I do them without a permanent home. I do it all while bouncing around the world. So I always remind myself that my lifestyle only functions well if I take the time to focus on my work and taking care of my mind and body. That ensures I don't simply give in to the allure of discovery all the time and avoid those things.
About how often do you change locations?
I'm on the road nonstop. In any one year, I travel about 9 months. Then I try to spend 3 months in one place or as is usually the case, the 1 month in 3 different places. But it changes all the time.
In the past 6 weeks, as an example, I've been in Iraq, Turkey, UK, USA, Portugal, Italy and Vietnam. That's quite standard for me as personal travel and work travel require, well, a lot of travel!
How have your travel preferences changed over time?
Naturally, as I get older, I prefer a little more comfort than I did in my earlier days. For example, nights in hostels are no longer an option. Also, now that I've seen so much of the world, I really prefer to visit destinations that don't receive a lot of tourists. I enjoy this style of travel because it allows me to meet people and hear the stories that don't really make it to the rest of the world.
I enjoy visiting beautiful sights but in the end, I seek out these connections even more. I really find it fascinating to travel to a place that few people have experienced because it doesn't seem interesting or there are major misconceptions about the destination.
Every place is interesting and preconceived notions are rarely correct, so traveling to such spots has become an important mission for me. This is why I go to places such as Iraq which is the perfect example of a destination that people think they know what's going on there but are actually incredibly wrong about.
How do you maintain a healthy social life and stable relationships with other people when you’re moving around that much?
It's all about paying attention to yourself and what you need. If I've been bouncing around for a while and I'm craving a better social life, I need to stop what I'm doing and go somewhere that can offer a better social life.
This is part of the reason I go to Lisbon often, a place where I know quite a few people. It's part of the reason why I suddenly slow down sometimes and stop moving around so quickly. If I need more of a social life, I make sure I get it. And luckily, there are many places around the world where you can find large communities of people that offer a great social life.
Also, if you can't or don't want to travel to a place where you know people, there are people everywhere that you could meet if you slow down. Pick any city, attend some meetups and before you know it, you'll havet hat healthy social life again.
So that's the key. If you need social interaction, make sure you go and get it. Don't let it build up. Otherwise, your travels won't be as enjoyable and the whole idea of living this lifestyle is no longer as valuable.
What about dating as a nomad, and in particular serious relationships? Any advice on getting into one while you’re nomading?
If you meet someone who happens to be on the exact same wavelength as you - able to travel the same amount, wants to go to similar places, travels in a similar style, etc - then that's wonderful and you can theoretically have a relationship while traveling around. However, that's not the norm. Chances are high that you won't be 100% on the same wavelength and you might be from different countries, have completely different schedules, have different travel interests, etc.
When this happens, you need to make a decision - what's more important? Do you want to continue your travels or is the relationship worth changing your lifestyle for? If it is worth it, then someone will need to adjust their lifestyle, and typically, both people will need to in order to make it work. That's often not easy though as it goes against why people started traveling in the first place.
The point is that it's a challenge as there are simply so many variables involved with this nomadic lifestyle and it's going to be hard to find someone that matches enough to continue in the same way you're used to. So sacrifice is definitely required in order to make a serious long term relationship work. That's it. Be prepared to sacrifice, but of course, it's no big deal to do so if the relationship is worth it!
Nomads have to keep material possessions to a minimum. How much stuff do you own? How have your gear and packing habits changed over the years?
I travel around with a 45 liter suitcase and a small laptop backpack. This is most of my stuff. I also keep one suitcase in storage in the US that mostly has things I've purchased over the years that might end up in my house if I ever get one. Apart from that, even though my suitcase is not big, it holds more than enough to keep me going and prepared for all kinds of situations.
I travel with 15 shirts, 4 pants, 4 shorts, 4 pairs of shoes, a travel iron and much more. In all honesty, my gear and packing habits haven't changed much over the years. Once I realized the benefits of a minimalist lifestyle early on, I stuck with it!
John’s note: From some of the other nomad bloggers I read, this is actually considered on the heavy side— many experienced nomads pride themselves on using the smallest backpack possible and only having like 4 shirts and 2 pairs of pants. I’m with Derek on this one– nomading isn’t camping, and it isn’t often that you actually have to carry your bag around for a long time, so there’s no need to go overboard on the minimalism. But then, I’m also a bit of a fashionista.
Is there any common nomading advice that you disagree with?
For me, the main issue I have is that being a digital nomad is often categorized as a job. Oftentimes people write to me asking 'how do I become a digital nomad?' as if the lifestyle is some kind of work you find somewhere. But being a digital nomad is just the lifestyle. Everyone needs to find a job first, or a source of income, that allows them to be a digital nomad. You can't simply say "I'm a digital nomad" and suddenly expect money to appear.
I see a lot of people quit their regular jobs to become a digital nomad without having a plan for how to earn a living. Again, they think 'digital nomad' is the job itself. So I have a problem with that because I think it's misleading and it causes many people to seek something that doesn't actually exist.
It's far more useful to understand that in order to be a digital nomad, you first need to find a way to earn money by either applying for jobs that allow such freedom or creating your own work opportunity that you can do from anywhere in the world. That is the most important step, and it's the hardest step by far. As a result, the focus should be on finding work that allows for the freedom of travel, not on traveling with the idea that the money will automatically appear.
How did you initially build your online following and start making a living? How hard was that?
I'll admit that I was a little lucky. Having started my blog back in 2008 when there weren't many travel blogs out there, it was much easier to get noticed. All I did was start writing blog posts that I thought would be useful for other people wanting to travel and that was it. Within a short period of time, people were finding my articles, leaving comments and writing me emails and my readership began to grow organically. That led to some high-profile interviews, a few articles written about me in popular publications and eventually to podcasts, all of which continued to grow my following.
These days, it's much harder to gain a following as there are so many travel blogs, so much information that is the same and so much content out there that really doesn't provide much value. Standing out these days is very difficult.
Have you found that the main “growth engines” for your business have changed over the years? If you were starting your blog all over again today, how would you grow your audience?
For sure. Back in 2008 when I started blogging, I didn't need to do anything except write blog posts. That was enough to start gaining a following since there weren't many travel blogs out there. And that's how I grew my blog, my newsletter and my tour company. It was all organic from trying to offer genuinely useful travel advice based on my own experiences and really trying to connect with those who found my blog. One thing led to another and here we are.
If I was starting all over again today, first, I wouldn't start a travel blog at all. There are hundreds of thousands out there these days and the idea of content has changed so much. People aren't necessarily searching for quality content these days, making it harder for a blogger to stand out. It's a very different game as the focus now needs to be on winning the Google ranking system game and/or social media algorithms.
Competing with thousands of other websites is not the same as simply writing blog posts and people finding your blog as a result. That's why I wouldn't start a blog these days as it's so much more difficult to grow an audience.
What are your main source of income today? Is it mostly the tours now?
My main business is my tour company. This is what I love and it's what I spend 95% of my work time on.
John’s notes: The other income streams *that I know of* are a couple of ebooks and some Amazon affiliate links to his recommended gear– both of which are aggregated on a Travel Resources page on his site– as well as the aforementioned donations.
Let’s talk recommendations– are there any travel or booking websites you strongly recommend, or any pieces of gear you consider must-haves?
I travel quite minimally, with one small 45 liter suitcase and a small laptop backpack (from Timbuk2, a company whose products I love). My favorite piece of travel gear is my tiny travel iron! As someone who lives out of a suitcase, I like to iron most days as it makes me feel a little better than always having wrinkled clothes on.
As for booking websites, I always use Kayak.com to check out flight prices and then book directly with the airline (or with points) and in general, I use booking.com for hotels in most places. It goes without saying that the whole credit card/points game, if done responsibly, is a major game changer for people that travel often. Finding the card(s) that work best for your situation and combining it with airline loyalty programs can lead to great benefits.
These days, I fly for free half of the time (and I take about 50+ flights per year), I have access to lounges in most airports around the world and the travel-related discounts I receive probably save me several thousand dollars per year.
Any particular credit cards you recommend for frequent travelers?
My main cards are in the Chase system. I have the Chase Sapphire Reserve and then the Chase Business Ink Preferred. And for personal or business, I have yet to find better cards. These offer the best chance of really maximizing the points you can accumulate while offering one of the best point to dollar ratios that exist.
Also, the long list of benefits are very useful for frequent travelers, especially the airport lounge passes and travel insurance. You can combine the points you earn from any 2 Sapphire cards so you could get the Sapphire Reserve and Sapphire Preferred (if you don't need a business card) and combine all the points you earn, making it even better.
What about health care, do you get traveller’s insurance or just pay out of pocket?
I pay for private health insurance in the US because, if I was dealing with something major, I would prefer to have the care done in my home country. Then, I also have travel insurance to cover me for any emergencies while bouncing around the world.
Have you found any good ways of dealing with jet lag or do you just work through it like everyone else?
Keep on traveling :) These days, I don't get affected too much by jet lag. I think my brain is simply confused all the time and it rarely has time to get too used to a time zone. But apart from that, with jet lag, you just need to give yourself a few days to get over it. There is no magic cure that eliminates it instantly so take a few days to relax, don't worry about having a weird schedule at the start of your trip, and before you know it, you'll be adjusted.
Now a special offer for my readers– Come to Iraq with Derek and I in April 2025
I wasn’t kidding when I said he had me sold on Iraq– I’m going. As of yesterday, I am signed up for his tour of Iraq that runs from April 3-15, 2025. And I’m inviting you to join me.
You can view the full details of the tour, and sign up for it, here. Enter the code JF250 at checkout to get $250 off the cost of your spot on the tour. Note that only a $500 deposit is required now, with the balance payable just after New Years– the discount will be applied to the balance, not the initial deposit.
I priced out the flights and other incidentals, and the whole cost of this trip comes out to $6000-7000, at least if you’re coming from Los Angeles. Flights are the main cost other than the tour itself and I’m about as far from Iraq as you can get, so it may be cheaper for you, especially if you’re in Europe/Africa/Asia.
If you’re thinking to yourself Seriously, Iraq? Isn’t that dangerous? I’ve got a funny story for you. I just put down my deposit yesterday evening, and then headed off to my biweekly Dungeons & Dragons (well, Warhammer Fantasy RPG if you want to get technical) game. When I got there I excitedly told the group that I had just signed up for a vacation in Iraq.
Three of them gave me some variation of the “Iraq, really? is that safe now?” response that I was expecting. But the fourth guy? He said Iraq is amazing and I’m going to love it. Turns out her was in northern Iraq a couple years ago, and Erbil– in Iraqi Kurdistan– is one of his favorite places he’s ever been.
So yeah, Iraq seems to be pretty cool now. I’m going to visit and I hope you will too– adventure awaits.