How To Live A Life Of Travel – Travel Lessons By Dustin Main

‘’I think of travel like being a kid again.’’ Dustin Main’s skinny escape started as a young child, ricocheting from one insane adventure to another. Never realizing that soon the world he had definitely hoped to gollop will become a subset of his larger than life travel plans. As a serial entrepreneur and an extreme hiker, his love for high altitude is just as feisty and unique.

Tripoto experiences their fair share of happiness when we get to settle for an instant confab with some of the most inspiring travelers of our time.


Yes! This week we bring you maddening adventures by Dustin Main as he shares his insights on how to live a life of travel.

1. Hi Dustin. Please introduce yourself to the Tripoto community and enlighten us about your travels?

My name is Dustin, and since late 2009, I’ve been traveling around and around (and around) the world in search for adventure.  Before leaving Canada to travel the world for a year, I managed an IT company in Canada which I still oversee from the road.  Since then, I’ve started / co-founded three other projects/companies including: The “Technology for Travelers” website Too Many Adapters , the creative photography collective Lightmoves Creative and my own website where I tell stories with photographs called A Skinny Escape
Since leaving Canada, I’ve visited all 7 continents, and lived on four.  I speak at events and lead seminars on photography, technology, and travel, and for the past three years, I’ve been working on a documentary photography project in Myanmar.  There I am documenting the rapid changes currently happening in the country as it opens up to the rest of the world.  I also work with a charity called “Do It in a Dress” where I’ll often go back-country hiking in a school girl dress to raise funds and awareness for education projects in Sierra Leone.

Dustin “Doing it in a Dress” on a cliff overlooking the massive Robson Glacier as it flows down Mt Robson, the tallest mountain in the Canadian Rockies.

2. How easy or difficult was it to venture out into the world as a solo traveler?

Of course there was anxiety at the prospect of traveling to the other side of the world, alone, for the first time.  There was a huge “unknown” factor, and there is only so much that research done beforehand can help mitigate.  That said, of course I was excited for this new challenge at my feet.
On the other hand, it’s pretty easy to do.  It’s never been easier, safer or cheaper to travel, and much of the world is accessible with just a passport, a visa card, and the clothes on your back.

3. You are a serial entrepreneur and run many online firms. How do you manage to keep up with your work and travel?  

It’s an ongoing challenge to be honest.  There is no doubt that managing productivity is much easier when you have a place to call “home” and where life is more predictable.  A comfortable desk, a predictable routine, and communication that you can count on makes a big difference in what you can do and how quickly you can do it.  Case in point: there is a very loud celebration / fundraising effort that is going on right outside my guesthouse window right now in Yangon (Myanmar / Burma), and goes on for about 12 hours a day.  Needless to say, it’s making work (and typing!) a challenge right now.I keep up with my day-to-day tasks with Google Calendar to track important meetings, Trello to manage to-do lists and groups tasks in my companies, and Google Hangouts to keep in touch.  I wrote a piece for Too Many Adapters called “9 Lessons Learned From Running a Regular Business From the Road” that details many of the things I did before I left Canada for a digital nomad life.I also try to separate travel for project work in places where I have limited internet access such a Myanmar / Burma with a place that I can relax in and catch up on my work.  A month for one, and a month for the other is a good way to look at it and make the best of both situations I find.

dustinmain-tripoto-3A school on stilts in the floating village of Maing Thauk on Inle Lake (Myanmar)

4. You have enhanced the art of story telling via your blogs. How do you think travel story telling has evolved over the years? 

The internet and technology is a huge game changer for storytellers everywhere.  Just think about how difficult it would be to publish a book, record a documentary, or to tell your stories to dozens or hundreds of people at once, even 10-20 years ago?  It’s incredible!
Now we can self publish our work, collaborate with people on the other side of the globe, and reach eyeballs that we couldn’t ever before.  It’s the democratization of storytelling, and it’s awesome.

5. As a consultant on adventure travel and technology. Do you think that now traveling and technology go hand in hand and one simply cannot plan their journeys without gadgets?

Technology is a tool, and you could say it can be used for both “good” and “bad.”  The access we have to resources while we travel with a smartphone or laptop now is immense.  Looking for a place to eat?  Simple!  Pull up google maps and read some reviews so you can pick the “best.”  It’ll even guide you there if you like.
On the other hand, what are we missing out when we only rely on technology?  I bet the guesthouse owner who has lived on this street all his life knows where the best meals are to be had, and maybe the little hole-in-the-wall restaurant he recommends with four tables sprawling out on to the sidewalk isn’t on Google.
So my advice is to use your technology wisely, and remember why you’re traveling in the first place.  Is it for the sense of wonder, and happy accidents that happen when you get lost along the way?  If so, relying on your smartphone might be killing the best part of travel.

6. ‘’A Skinny Escape’’ sounds very catchy. Was it a conscious effort to distinguish your travel blog from others or was it a spontaneous take?

There is a funny story to the name actually.  When I left Canada, my blog was thrown together at the last second so that my Mom had a way of following along and making sure I was still alive.  I gave it the name “Skinny Backpacker” for my svelt body type and the backpack I’d be carrying around.
A couple of years in, and as I began working in travel, the “backpacker” part of the name was causing some issues.  In Canada, “backpacking” is the term we use for multi-day, backcountry hiking trips.  On the other hand, in many parts of the world “backpacker” is synonymous for “drunken gap-year kids vomiting on the beach.”So I wanted to keep “Skinny” in the name as a lot of people knew me from the blog name, and I wanted to ditch the “backpacker” part.  I came up with “A Skinny Escape” because it reminds me of just barely making it, like Indiana Jones sliding through the secret passage just in time, and reaching back at the last second to grab his hat before the door closes.  It’s also about escaping the routine of everyday life.
dustin main

7. Out of your photographic project, would you like to share the best one with our Tripoto community ?

I’ve had the wonderful opportunity to travel with both of my parents over the years.  In early 2013 I brought my Mom to Myanmar / Burma, a country that I’ve been working on a documentary photography project in for the past three years.  I was a little concerned that it might be too difficult for her to travel in, but she’s a bad-ass and we had an incredible time.
On one of the very early mornings we had, I led her by motorcycle to rarely visited temple in Bagan to watch the sunrise from.  I can honestly say that it was one of the most incredible sunrises I’ve ever witnessed, and it felt so great to be able to share that with her.
dustinmain-tripoto-1Sharing the sunrise as it washes over the temples of Bagan

8. As a traveler, what is the biggest challenge you have faced on the road?

When you have traveled for some time, it’s easy to become a little jaded.  After awhile, waterfalls can lose their charm, and important religious monuments start looking the same.  If it’s a comparison game, why not quit after seeing Mt Everest, Niagara Falls, and the Taj Mahal?I think it’s important to give every experience its due.  That waterfall might not be as pretty or tall as others you’ve seen, but it’s still beautiful on its own, and just because you’ve been on the best hiking trail in the world, doesn’t mean you should stop hiking.

9. Any advice for people who want to quit their jobs and travel but aren’t?

If you’re waiting for the perfect time, when the stars align and the bank account is bursting with cash, and there are no strings holding you back, I’m sorry but it’ll probably never come.  You can always save up more money, pack a little better, have a better pair of hiking boots… but the real thing you have to do is just GO.
You just need to tell your boss that it’s time for a sabbatical.  You need to sell the belongings you no longer need.  You need to find someone to take over your lease.  It’s just a series of things to check off, and an airplane to board and then WHOOSH, it’s happening.
It’s not rocket science, and I don’t know anyone who has told me “oh I wish I would have done this when I was older.”  On the contrary, what I hear is “why didn’t I do this sooner?”  People from all around the world, and from completely different circumstances are doing it, so there is no reason why you can’t too.
Just go and do it.

Inspiring enough? Let the stories stir your bubbling spirit to travel the world, pick up that ever-expanding bucket-list and share your stories on Tripoto.