Meet Derek Freal, an American cubicle escapee living the nomadic dream. I should probably point out that Derek is not the elderly gentlemen with the great smile in the cover photo but the man behind the camera of this amazing shot. As far as I know, Derek has a great set of chompers and an even greater love of  the unknown. He is a seasoned traveler and the man behind the Holidaze, a blog documenting his slow and unique journey around the world.  From a game show appearance in Indonesia to partying with the Yakuza in Japan, his life abroad is an interesting one to say the least.

I recently sat down with Derek (via email) and asked him a few questions about his current mission – visiting 80 countries over the next 4 years.

Brief Bio:
I bid adieu to my house in Austin, Texas for a backpack and the freedom of a nomadic lifestyle all because of a Disney movie. That’s right, the Lion King. My enlightening came from the song by Elton John, Circle Of Life, and it’s lyrics “there is more to see than can ever be seen, more to do than can ever be done…” I wanted to see if this was really true.

It all began in 2008 when I took a 90-day leave of absence for the last quarter of the year and moved to Tokyo, Japan. There that I not only fell in love with Asia but also with the sensation of being completely out of my element. In fact I love places where the local writing looks like squiggles — just don’t tell any of the natives that. After returning to work at the beginning of 2009 it quickly became clear that I could not resume the mundane cubicle lifestyle again and within a few weeks I had resigned from work and headed back to Asia.

You have been documenting your trips since 2009  but over the next 4 years you will be embarking on your biggest journey yet. What led to the decision to sell all your possessions and head out for 4 years of unknown certainty?

Well, first off I should correct you there: although I have written about my adventures for five years now, the first three years of that consisted of little more than drunken rambles intended solely for friends back home, so they would know I wasn’t dead. Although they are still online to this day, anyone who does not know me personally would have no interest in reading them.

It was only in 2012 that I finally decided to get serious about travel writing and began writing posts that were exciting, informative, and hopefully inspiring as well. Although I had returned to the States every few months since first embarking on my global learning adventure, by this time it had became clear that there was no real reason for me to keep doing this. All of my friends were married, had kids and families, and even when I would be back in town it was hard for us to coordinate schedules. So in early 2013 I sold all my possessions and hit the road permanently.

TLITs: Ha! This is like interviewing myself.

You also mentioned that this was somewhat of an impromptu decision. How did you plan and prepare for such a huge adventure?

Truthfully? I opened up a map and drew a squiggly line on it, then checked visa entry requirements for a few of the tougher countries, like Iran, Afghanistan, and North Korea. In fact it took longer to write the post about my RTW adventure than it did to actually “plan” it. Speaking of I keep forgetting to check if any shots are required along this adventure…

One thing that sets me apart from almost every other travel blogger is that I don’t plan. Anything. Ever. When I wake up I have no idea what I’ll be doing that day, let alone where I’ll be in a week or even a month. I have found that this leads to exponentially more adventures. Of course it is not for everyone, but without living life like this I would certainly have a lot less entertaining stories to tell.

People often have “walk into an airport and spontaneously buy a plane ticket leaving that day” on their bucket list. Well, that is how I buy all my plane tickets. Sure, sometimes than can be a bit expensive being last-minute but other times they have been dirt cheap. I’ve taken more international flights for less than $100USD than I can even count.

TLITs: Hmmmm…I love to plan. You may be Bizzaro world me!

Although I’m sure selling off your house and life in Austin helped, how are you sustaining yourself over 4 years through 80 Countries? Unless of course that was one helluva house in Austin!

Well my problem is that I’ve already been living and traveling off my savings for five full years this March and in all honesty it’s not going to last me the next four. It probably won’t even last through the end of 2015. That’s part of the reason I’ve gotten more serious about both the quality and frequency of my writing. It’s time to start bringing in at least as much money as I am spending on the road. In the past I have done a bit of freelance web design work, but only by word of mouth and always for ridiculously cheap prices. However over the holidays I designed a web site advertising my abilities (http://Derek4Real.com) and have started offering to help other travel bloggers just to help get the word out. Supplementing my blog income with a secondary income should help make sure I don’t end up broke halfway through this adventure. Although ideally as I get exponentially more committed to travel writing so too should the income it provides increase. I know countless people who have had amazing experiences teaching English for a year to rebuild their savings before resuming their travels but that is not for me. Not only do I dislike teaching but to be perfectly frank I kind of hate kids, at least when in large groups.

Your (admittedly loosely) planned route is very interesting. Why have you decided to travel slow and low – only traveling by land and sea for 80 Countries over the next 4 years?

Foreign visitors learn more about a country when trans-versing it from one side to the other. Flying in and out through the capital city airport denies you so many opportunities for explorations to the far corners of a country and encounters with locals. Especially in Asia where cultures differentiate so much from one region of the country to another.

Of course if you only have a week or two then traveling by bus from one corner of Costa Rica to the other is not the most feasible idea. You’d spend the entire time on buses and miss out on much of the culture. In order to make land travel work, you have to be willing to go at a slow pace and take your time. Savor the moment.

In terms of my own four-year trek through 80 Countries, I should however point out that technically I already broke the land/sea travel only aspect of this adventure. The first time was in Indonesia when I had to fly out to do that film. Since then…well it’s like “breaking the seal” after you’ve had a few beers. I just started flying everywhere. But I’ve put an end to all this. I’m in Vietnam right now exploring the country by motorcycle. After this is Cambodia and Laos and then onward!

Part of your travel plan included a visit into North Korea. What is your history with this closed off country and why do you want to visit?

I’ve been fascinated with North Korea for as long as I can remember. It’s one of the last closed off and ethnically homogeneous countries left on earth — how could you *not* want to visit that before it changes? Don’t get me wrong, there are plenty of atrocities committed in that country — as in many many other countries — but times are changing now and we’ve most likely only got a couple of years left to see the DPRK as the conundrum it currently is.

What makes that one difficult is that as an American passport holder I have to relinquish said passport in Beijing and board an old rickety communism era Soviet plane to fly into Pyongyang. No doing North Korea by land travel, I’m afraid. This is the one big exception to my land travel goal that I’ve known I would have to make since day one. I also have to visit there before South Korea because if they see that stamp in my passport while in Beijing then I will be denied entry to the DPRK.

Another interesting stop along the way is Iran. What is your intrigue with courtiers that have little interest in welcoming you in?

I just like going places where most people don’t. If I could have somehow squeezed Somalia into this trip then I would have. Just because some places might not have the best reputation does not mean that everyone living there is all bad. In fact quite the opposite. I’ve found that there are good people all over the world, just as there are, unfortunately, bad people all over the world also. To my surprise Iran actually offers 7-day visas for Americans. However it should be noted that even with an approved visa entry into the country is not guaranteed. In the end it all depends on the mood of the immigration officer that day.

TLITs: So very agree.

Currently you are living in Indonesia. What is your draw to that country and what’s next for you and the Holidaz Blog and website?

When I first arrived in Indonesia I was only planning on staying for one month before moving on to Singapore, the next country on my RTW trek. However when the Singapore Smog started in mid-2013 I realized there was no point in visiting the country if I couldn’t even enjoy the outdoors, so I extended my stay in Indonesia another month.

During that second month I started to meet famous Indonesian travelers and writers such as Riyanni Djangkaru and Trinity. Soon I found myself hanging out with the “in” crowd and by that point I didn’t want to leave. Next thing I know I had done a film, two television appearances, and had even been interviewed by a magazine, all within three months.

Don’t get me wrong, I love the country, the culture, the food, the amazing beaches and the 17,508 islands that all need exploring. But it is definitely because of the amazing friends that I have stuck around so long. Never have I had such good fortune with any place I’ve visited! It was with a sad heart that I left Indonesia this week but alas, I have to continue my RTW trek.

Any parting words for those thinking about packing in their 9-5 life and heading out for a life of the unknown?

Never let fear of the unknown hold you back. This world is an amazing place that is just begging to be explored. Of course once you start it is very hard to stop so I recommend saving up a little bit of money first.

For anyone who does decide to do long-term travel, be sure to start a travel blog. Not only is it a great way to inspire others but that will also allow you to bring in a little income while on the road. My biggest piece of advice there would be to start blogging at least six months before leaving. That allows you to build up readership prior to embarking and ensures that when you do start writing about your life on the road there will be someone else reading about them.

Quick Questions:

Best Moment while traveling

Making friends with a member of the Yakuza and getting the opportunity to see the back-door VIP side of Tokyo. The parties, the clubs, the food, the women — all amazing! Plus I finally got to check ‘nyotaimori’ off my bucket list. Or in layman’s terms eating sushi off a naked woman.

Worst…

Ending up in a Mexican jail thanks to a drunk (and stupid) friend who, let’s just say, tried to buy something he shouldn’t have from an undercover. We were all thrown in jail and taken for everything we had on us — wallets, watches, phones, anything of value. Luckily we were released in the morning.

TLITs: Ha! I came close to this too!

Best Tourist Site

This is a tough one. Several of the Mayan sites in Mexico and Central America are pretty humbling. The Burj Al Arab in Dubai is also impressive, although buying drinks at the Sky Bar are ridiculously expensive. Mount Fuji in Japan is also amazing. Borobodur in Indonesia is cool as well, just always crowded.

Worst…

Bali. The beaches are crowded and full of hawkers and salesmen — relaxing on the beach by yourself is just not possible. Everything is over-priced and the locals are only friendly if you are giving them money. There are hundreds of more beautiful, less-crowded, less-expensive and hassle-free places to visit in Indonesia — not to mention more virgin beaches than you can ever imagine IF you just get off the tourist path.

Best thing you put in your face hole while traveling?

Local cuisine, obviously. If you don’t know where/what to eat just follow a local until they stop for food 😉

Worst…

McDonald’s. I want to slap every foreigner that I see eating at a McD’s instead of sampling the local cuisine. Why bother even traveling then?

Best quote from your trip

I love everywhere I’ve ever visited. I just don’t love some places enough to feel the need to return a second time.

Derek Freal is the founder and head traveler of theholidaze.com. He is currently wandering without plans in South East Asia. To follow along his 80 Countries over the next 4 years tour check out his blog or connect with him on Twitter, & Google+

All awesome pictures provided by Derek of the Holidaze blog