How to Hack your life & live in paradise with Quest Henkart

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Quest Henkart is a self taught digital dirtbag with an impressive array of travel friendly skills that have enabled him to build a truly sustainable lifestyle around the world.

In this interview Quest goes deep into how he funds his adventures, what it truly takes to set yourself up as a digital nomad, how to switch gears when not travelling and also some important tips on how to always travel smart.

His success in developing his lifestyle has been built on a well calculated mix of attitude, deep personal desire, as well as a ton of grit and hard work — Quest is a truly inspiring Digital Dirtbag!

So be sure to strap yourself in and get your notebook out, this interview is full of wisdom and worthwhile lessons everyone can benefit from!

Welcome, Quest Henkart.

Quest Henkart

Quest Henkart

Q: Can you tell us a little bit about yourself, namely how and why you got into climbing, travelling and adventuring around the world?

Well, I sort of found climbing by accident. I had just graduated from University and was lining up the first step in my career. As the months wore on, I saw that my perception of happiness was directly correlated to the possessions that I had and the money I was making. I had a bit of an epiphany and decided that this was not the direction I wanted to take in life, so I sold everything I owned and used that money to book a one way ticket to Thailand.

I was completely broke. I had a small amount of money coming in every month from a sublease, but other than that I was travelling with the intention of finding work along the way. Within a week of arriving in Thailand, I accidentally found Tonsai and immediately fell in love.

I befriended a local climbing guide who taught me how to climb and lent me gear for free, and got a job at a local restaurant. Over the course of the next year, in my search for sustainable work, I learned how to make jewellery, became massage certified, learned how to Fire dance (and get paid for it), and became a Scuba Instructor.

Over time, travelling became my passion, rock-climbing became my purpose, and diving became my means.

Ha Long Bay, Vietnam

Ha Long Bay, Vietnam, a climbers and divers paradise. Taken from Quest’s Blog.

Q. It seems that you truly do live in the “digital world”, can you give us a bit of a background on what you do?

Over the course of my years abroad, I began to notice a growing trend. While I was working long hours at a dive shop or out on the boat, there was a growing number of folks who just worked a few hours a day and made a western salary. Their secret was to work remotely as a Software Engineer or on some sort of app development.

Before long, I had decided that this was my next pursuit. With growing access to WiFi and data plans in the most remote regions of the world this seemed like the perfect opportunity for a traveller. I began diving into online tutorials and learning everything I could get my hands on. I immediately fell in love.

As I continued learning and developing my skills, I realized that I was not learning fast enough. I needed something to catch me up to the competitive market so I could actually begin to take advantage of my new found passion.

This is when I discovered Software Engineering boot camps. These boot camps are popping up all over the world providing opportunities for folks to re-tool or enter into a new industry without years of training and education.

In just three months, a person with no previous technical experience can get a job as a medium-level engineer and a 6 figure salary (depending on location of course).

After some searching, I found the best one, Hack Reactor, which was as intense as possible and as advanced as I could find. You can check it out here.

Hack Reactor

The school boasted a 99% hiring rate upon graduating and a $105,000 average starting salary, allowing people to take the course remotely or in person. At 6 days a week, 11–13 hours/day, at the end of the 3 month period, a person would have 1000 hours of applied training, education, and real development experience, along with lifetime job placement support which can really come in handy when finding jobs remotely.

I am currently in a bit of a transitional phase. For the first time in many years, I have an apartment in California and I’m looking for a normal Engineering job. However, this phase is only a temporary one.

I plan on investing these next few years saving money, and further mastering my skill set. Next step, buying property somewhere like Kalymnos and putting together a small tech commune, where we work for a few months out of the year, and then climb and enjoy for the rest.

The best part about being a software engineer, is that the job demand only increases, and not only does working remotely help the local economy by pumping money into it and not taking jobs, but my ability to survive is totally independent from the location in which I live.

Quest working from home.

Quest in his element as a freshly graduated software engineer

Q: On top of your “digital skills”, you’ve also got a pretty impressive “adventure” resume, can you share the other cool skills you’ve developed, and how they have helped fund your travels?

As a result of my clear intention of finding sustainable work on the road, I have built a very impressive travelling resume for myself and a garage full of certifications. Although only two of them turned out to be sustainable and profitable. These two were Fire dancing and Scuba Diving.

I fell into Fire dancing in Tonsai, it began as just a hobby, and quickly evolved into a passion, before long I was getting paid to do it.

I started my company “Meditation in Motion” when I moved to Honduras back in 2011, and obtained my first residency at the most popular club/bar in town. Twice a week I would perform on their busiest nights. I would drink for free, the bar paid me $20, and I would make anywhere between $20-$150 (average about $50) in tips. This alone was plenty to live off of on the tiny island of Utila.

A photo of Quest scuba diving

Playing about in the deep blue sea; not a bad way to earn a buck as a dive instructor!

When I was living in Greece, the coins there are worth a lot more (thanks Euro), and I would charge the bar €50 and make €150–250 in tips. Enough to pay rent for a 15 minute performance.

In the States, I would charge $200–500 for a show. But in other places, a fire dancer wasn’t so profitable. In Thailand, almost every local beach bartender is also required to be a fire dancer. They don’t get paid extra for it, so why would the bar pay a foreigner to perform.

For a time, I would get free drinks in exchange for a show, until I won 2nd place at an international Fire dancing contest in Thailand and people began offering me $15 to do a show at their bar. Still hardly profitable compared to other locations.

During the day I was a Scuba Instructor.

Being a Scuba Instructor was the most profitable, but also the most time consuming job.

Unlike DiveMasters (underwater guides and one level below Scuba Instructor), getting a job as an Instructor is extremely easy, in fact, anywhere in the world where there is a diveshop, they literally beg passing instructors to work for them.

There is no shortage of work, and that means a guaranteed job in any tropical location in the world. Pretty sweet deal! And the work is a lot of fun too.

However the hours can be pretty long. When considering prepping the boat, working the shop, logistics and management, not to mention actually teaching courses. This was a 12 hour/day job.

It paid really well though, and freelancing was a lot less time consuming (freelancers ONLY teach courses, no extra work, but get paid less). While this is extremely dependent on location, Instructors generally make $80–100 per person for a 2–3 day course.

Courses generally have 3–6 people in them. Suffice it to say, if I taught 1 course of 4 people in Thailand, my expenses for the entire month were paid for. The rest of the month was reserved for climbing.

Quest putting on an impressive show in Tonsai, Thailand.

Quest putting on an impressive show in Tonsai, Thailand.

Q. What are three essential tips you would give to anyone who wants to travel cheaply, for as long as possible and even make a buck along the way?

First of all, I always assume I can’t afford anything. Even if I’m not broke, I just pretend I’m broke. I tend to spend less that way. Also understanding that there is nothing wrong with someone else’s half-eaten food.

While I was doing my DiveMaster training in Koh Tao, I completely ran out of money. Dead broke. I survived by couch surfing amongst my friends, and taking advantage of the gigantic portions the restaurant served at the diveshop, and the leftovers that patrons left behind.

I developed a funny reputation at that Diveshop, but I ate like a king everyday (okay maybe a dirtbag king) and didn’t spend a penny.

Now that travelling with a mobile device is the norm, there are a ton of apps that simplify the process and are much more effective than following a “I can’t afford anything” mindset. These apps track our daily spending for us, and keep us in line with our budget.

I recently began to use an App called “Daily Budget” on the iPhone. It’s really awesome. I set the amount of money I want to spend that month, and it keeps track of my daily limit. Everything I buy, I throw it into the app and it keeps track of whether I am below my daily limit or above, and carries the surplus or deficit over to the next day.

Q: Because you‘ve been on so many expeditions around the world, do you have any tips to handle the change from “adventure/fantasy" back to the “real world”?

This was an entire skill in itself and took me a long time to develop. The reverse culture shock is probably one of the reasons I just kept on travelling. I only could last a maximum of 2–3 weeks in the States before I threw my hands in the air and took a one way trip somewhere else.

Over time I began to develop a way to handle this transition, and now I can do it in a day. I have what I term “island mode”. That’s me when I’m travelling. Island mode carries with it certain personality traits, ideologies and a specific mindset.

Then I have “city mode”. City mode has its own set of traits. I can interchange these ‘modes’ like changing a hat. I have learned to enjoy specifics from both modes, and I always know that I can switch back at any time. All it takes is a passport and a plane ticket.

It takes time to develop that skill, but I think accepting the fact that we, as individuals, are different when in these drastically different environments is what makes it easy. At the beginning I refused to change out of my island mode. I refused to put on jeans, take off my jewellery, and could not understand why people did the things that they did.

But really, that point of view is just as culturally insensitive as the city person who goes to the island and calls it dirty and disgusting and goes back to their resort. The idea is to celebrate and participate with each culture for the things that make it wonderful, and with that mindset, we can find joy anywhere in the world, even at home.

A photo of beautiful Kalymnos!

Kalymnos Magic!

Q: What is the one piece of actionable advice you would give to anyone looking to organize a long term, tropical island, rock climbing adventure?

I think the most important advice I can give anyone who has a desire to travel the world or wanderlust is AVOID DEBT. One of my favourite quotes:

“Gold is the currency of Kings, Silver is the currency of princes, Barter is the currency of peasants, and Debt is the currency of slaves”

Debt is really the only thing that can hold someone back from their dreams across the world. Money can be made abroad, and a person can travel to a country where a few hundred dollars can last them for months if spent wisely. But if they have debt, whether it is cell phone payments, car payments, house payments, medical payments, education payments. Those are the things that won’t go away, and a local income in Thailand (which is enough to get by in Thailand), won’t even come close to paying the bills from back home.

Avoid debt at all costs, if you aren’t in debt, then you are truly free, and the world is your oyster.

It’s also important to have some sort of emergency fund. Shit happens and when it does, you need to have some emergency plan. That means either a credit card (I know that sounds hypocritical after my rant about debt) for emergencies only, a savings with a few grand that you don’t touch, or some family back at home.

Travellers insurance may seem like a waste of money until you need it, it’s an investment that everyone should make. My life has been saved by travellers insurance when I had it, and I nearly lost my eyesight in my left eye another time from not having it (It was saved by my emergency fund, but it also emptied my savings). You should not travel without at least one of these fall-backs. Things can go terribly wrong, and when they do, you need a way to get out and get away as fast as possible.

As far as jobs go, all the jobs I’ve ever got abroad have been acquired upon my arrival, although doing it in advance is probably a lot smarter. The more money you have saved the more comfortable you will be and the most fun you’ll have, but don’t let a dollar sign keep you at home either.

A loose plan is nice to have as well, but it is important to keep it flexible. Become a yes person, and don’t stick to your plan, just have it in case a better one doesn’t present itself.

Q: What do you see yourself doing in the long term? Still travelling the globe or eventually settling down in one place having a family, job, house…?

Like I mentioned before, my current stage in life will be spent preparing for my next big thing, which will be a tech-based sustainable intentional community somewhere in the world with incredible climbing, on the beach, with lots of slacklines.

The goal is to work, perhaps in consulting, remote or contract work for a few months a year, and then spend the rest of the year enjoying life. This is my 3–5 year plan.

Quest attempting a massive slackline.

Quest biting off a bit more than he could chew with this slackline attempt

Q: And finally, what are your three favourite climbing destinations and why?

El Potrero Chico, Hidalgo, Mexico

Home of the tallest sport climbs in the world (24 pitches anyone), incredible food and culture and crazy multi pitch climbing.


Beautiful limestone, incredibly cheap, gorgeous beaches, huge climbing atmosphere, and enough climbing mountain goats to make you wish you had hooves.


I saved the best for last. Don’t listen to all the hype about how this place has changed. It’s still the same place, with the same community, locals, and climbing. Words can’t express how much this place means to me, well actually they can. I wrote this poem a few years ago, I don’t think an explanation can do any better:

The limestone cliffs provide the key

As I head forth to where I’m free

the Jungle builds devouring the beach

as Climbers climb and buddhists preach

We float on bright, vibrant blue water

where fire burns, and only gets hotter

here buckets are filled, and slacklines are set

and the true adventurers are those we just met

in bungalows we stay right on the sea

with backgammon in hand we enjoy our tea

music we play near every day

as base jumpers jump right into the fray

the food is the best, curries and all

and climbers scream whenever they fall

at night we drink while fire dancers spin

and all those we meet become our kin

true in the heart and pure in the mind

all of the locals respond in kind

this is the place where I can be me

where beauty flows as far as I see

and surrounded by this glorious rocky rampart

at last I return to the true home of my heart.

A stunning landscape photo of Tonsai

The one, the only… The beautiful Tonsai

To read more about Quests adventures around the world then be sure to check him out online:

Quest’s old TravelPod Blog (2010–2011)

Quests Tumblr Blog (2012–2013)

And for all things tech, business and software you can also get in touch with Quest at:

If you think you would be a great fit for the Digital Dirtbag series or know someone who might be interested in sharing their story then feel free to shoot me a message on Instagram @adventureinmyveins.