From leaving a six figure cubicle job to living a life without limits

When Matthew G. Bailey realized that money is not the equivalent of wealth, he already had a 6-figure future within his grasp at age 23. But he left his promising career in real estate for the freedom to experience everything that life has to offer.

Now he is traveling the world, pushing himself further everyday with new challenges and connections, while enabling others to do the same, on their own terms, and on a limited budget.

Life is too short to live within limits. Read my interview with Matthew for a jolt of inspiration!


1. Het Matt, how did you end up on the wrong career track? What ideas or expectations were holding you back from recognizing and going after your dreams?

I think the biggest thing holding me back was thinking I needed to make a fortune. I, like many others I presume, thought success was getting rich financially, especially by my own terms, and then owning a lot of stuff. Growing up in an oil-town where everyone around me made six-figures for simple jobs twisted my perception on life. No one I hung around with had any cool dreams or ambitions. It was mostly greed and buying the biggest house, boats, a bunch of expensive toys that are almost never used, motorhomes, and the standard pre-packaged vacation. My “dream” was to break away from this blue-collar world, get into business, be financially rich and then also buy a big house, a Ferrari and a bunch of other cool stuff. The difference was that I wanted to do it on my own by creating a business or investing BUT in reality, the end-goal was the same.

Matt1At the same time, I wanted to escape the surroundings I had found myself in. The lifted trucks, the mindless chatter, the drunken weekends and all that other stuff so I moved to a new city, which really gave me a new life. Suddenly, I was living on my own with no family or friends. This forced me to be a little more extraverted and to meet new people. It also gave me the freedom to be who I wanted to be without all the stigmas I had in my hometown. I found that I was much more outgoing then I realized and I also found myself willing to try new things like learning how to salsa dance, acting in movies and trying out for the Olympic speed-skating team with no prior experience.

Long story short, my dreams slowly changed. While I certainly carried the same dream for a few years, which got me into real estate investing, it all changed when I finally took the solo trip I had been dreaming of for so many years and jumped on a plane to New Zealand and Australia. It was this trip, combined with some great books like the 4-Hour Work Week and the Tipping Point that gave me a new mindset on life. I began to actually think about what lifestyle I really wanted and whether I actually needed to be financially rich or whether I just needed to be time-rich. Suddenly, there were more riches than just the financial type. I had a taste of life that I didn’t have before.

I knew I wanted freedom more than boatloads of cash. I knew I wanted entrepreneurship, which is actually what I was as a child. I knew I wanted the ability to try new things, meet all sorts of interesting people and the ability to travel the world if I want to. All of these things helped me realize that real estate wasn’t a path for me. At least not in the way I was planning on.

2. How did you get the perspective that you needed to examine your lifestyle, to discover what you really want (freedom)? What was this process like?

I began to really look at the people around me. I looked at the successful people that were retired and had big pensions and the people who were heavily investing in real estate or working in the corporate world. Suddenly, I realized that most of them had no life. Even though they had money, they couldn’t really make effective use of it because they were too busy or had no imagination. They would drive their fancy cars to and from work and that’s about it. Maybe on the weekends they could enjoy a day. They were stressed and getting older. Others were bored but stuck in the same mindset that got them there in the first place. I think one of the biggest realizations was with retired people. These people worked most of their lives and even had pensions they could live on for the next 40 years. Yet, most of them who I spoke with were bored. They were so used to have something to do and the jobs they worked (most of which they didn’t enjoy) really hammered the imagination out of them. From my mindset, I could see how free they could be with a pension and time but with their mindset, they felt broke. They were still trying to live the same lifestyle as they did when they worked even though the “ball and chain” was removed. This really made me think deeply about the future.

Matt3I began to ask myself if I really wanted to work 30-40 years just for works sake so that I could “retire” and finally have time to do what I wanted. Of course, that’s if I made it to retirement. Everything is a gamble. I know of some who died within a year of retiring. Some never made it. I gained a new appreciation of life in the process of watching other people.

After reading the 4-Hour Work Week, it really changed three things in my head. First, it made me really examine the true cost of living. The cost of a life I’d be happy and content with. Second, it woke me up to the possibility of living in different places or even different countries, which might suit my lifestyle better. Lastly, it made me think differently about work and entrepreneurship. I’ve always had the entrepreneurial bug but learning about digital entrepreneurship really made my imagination fire on all cylinders. Better than that though, it made me question retirement. If I was doing something I enjoy doing, why would I want to retire? People don’t retire from work they love – they keep doing it until they physically can’t. Actors don’t just retire from acting because they turn 65. That would be insane. They LOVE what they do. It gives them meaning. People only retire from jobs they don’t like. If I don’t have to retire, then I don’t have to focus on having millions in the bank to live a life of excess in the latter years. Plus, I didn’t want to live a life of excess anymore.

From a financial point of view, if you do a lifestyle analysis and realize that you no longer need $10,000 monthly to make it happen, the freedom gates fling open. It’s amazing how many people are held back by simply thinking they need more than they really do.

3. How did the people close to you— your family, friends, and coworkers—react to your decision? How did you explain it to them?

I love my family. While they probably worried that I wasn’t taking the normal path and working in an office or whatever, they didn’t really say much to hold me back. They are pretty supportive of whatever life I choose. Most of them always imagined I would be an entrepreneur, considering how many little businesses I started as a kid BUT no one ever thought I would be a minimalistic traveling nomad of sorts. I don’t know if I said that right but basically I think they imagined me as a “Shark Tank” type of entrepreneur with all the fame and glitter to go along with it. They always imagined me as a multi-millionaire and while that may still happen, my mindset has shifted away from the padded bank account to be more focused on an incredible lifestyle.

Most of my past co-workers and friends I was close with always told me I would be okay doing whatever I want to do because they felt I had a really good way of thinking, a really good drive in life and overall had a good head on my shoulders. I’ve heard that a lot in life and I think that has helped me push forward with an unconventional path.

4. To what extent was traveling essential to making this mental shift? What experiences did you pursue initially?

Travel has had a big impact in my life and certainly helped change my mindset in the beginning. My first big trip was really just moving to a new city. That was certainly a big step for me and allowed me to create a new self. I found new friends, found my own apartment, found new interests and basically created a new me.

Matt5My next big trip was going to New Zealand and Australia for five months. Part of the mental shift had nothing to do with the destination but with the act of going. It was a dream I had for years but kept putting off hoping that friends would join. Finally, I went alone and it was one of the best decisions I made, despite some real estate investments blowing up in my face when I was gone. Finding the courage to take such a big leap radiated throughout my life. When I was overseas, I found parts of myself that I didn’t know existed. Suddenly, I was bold enough to try things like bungy-jumping, skydiving, hang-gliding and scuba diving with sharks. I found out that I loved thrills and loved pushing my limits. I became much more willing to say yes to things and four months into the trip, found myself booking a ticket to Bali, Indonesia. At this time, I didn’t know what Bali was. Some friends told me they had been there and that it was a great place. That’s all I knew. I didn’t even know I needed a visa until I got to the airport. It was blissful to be so ignorant at that time. I just took it all in, made friends with traveling strangers and Balinese locals, jumped on motorbikes with them for my first time and had an amazing time exploring new lands.

One of the biggest things I gained from my travel experiences was courage. I felt like I could do anything I wanted to. I felt my self-imposed limits shedding themselves from my soul. The world seemed much bigger and suddenly I could see myself doing things I didn’t even imagine before.

Another benefit from travel has been learning how cheap it can be and how cheap travel is actually better than expensive travel for expanding the mind and truly learning new things. Suddenly, I realized I could travel cheaper than I could live at home, which I found mind-blowing.

5. Did you learn any new skills or adapt your competencies to become a digital nomad?

As of now, I still do 99% of things on my own, which means I’ve had to learn a lot about WordPress, social media, SEO, writing and all the basics with starting online businesses. I learned the hard way that blogging isn’t a good way to make an income and I also learned that simply meeting successful people would not make you an entrepreneur.

It took me a while to learn that I needed to actually find a need in the marketplace and then test that need to see if people were willing to pay for it. I think I had this idea that it would be super easy.

In terms of being a digital nomad, I still find working from the road very difficult because I’d rather be out on an adventure than sitting behind a computer. From my experience, I think I am better designed to form a home-base for a certain amount of time and really get things done. If there’s anything I’ve learned from working on the road, it’s that you can’t do it while backpacking in the traditional sense. You can’t be moving every week or less and expect to get enough work done to run a business. It becomes too stressful finding WiFi and settling down.

Whenever I meet people who want really want to travel but mention starting a business because it sounds so awesome, I tell them to travel first without the stress of having a business to run. Everyone should do a long-term trip without a laptop at least once in their lives.

6. How did you fund your adventures at the beginning? And how have you created new sources of income through location-independence? What do you do to sustain your lifestyle of adventure?

In the beginning, I just did it the old-fashioned way and saved money from working jobs. I decided to stop spending money on things that were no longer bringing value into my life. I also became much more involved in fitness and gave up partying as much as I was, which saved me hundreds of dollars every month. I lived as cheap as I could and saved everything for travel. I would then quit whatever job I had and head overseas.

Since then, I’ve been busy creating online businesses because I really want to make this my lifestyle. Sometimes I’ll work on my online businesses while working a few months every year at home to save as much money as possible. I now use “travel hacking” to earn hundreds of thousands of points, which pay for my flights. I’ve also taken my writing skills more seriously and have been getting a lot of free activities in return for writing about the adventure. This doesn’t help offset the cost of my main travel but it does bring a lot more adventures into my life that I may not be able to do otherwise.

I’ve also been growing Canadian Free Flyers to become my main source of income but have a lot of other ideas I’d like to get out there as well. It’s a lot of fun to think of an idea and then create it.

7. You’ve started a few successful websites to share your passion. What have you learned about online entrepreneurship in the process?

I’ve learned that it’s not as easy as it sounds. There are a billion ways to make money online and choosing a route can be one of the most difficult decisions to make. A lot of it comes down to focus and making sure you see a project into fruition. Many people, including myself, get caught up trying to create project after project without seeing them through to the end. I’ve also learned that it’s a good idea to start with what you know, assess the marketplace, find a gap that you can fill and then start a business that serves that niche. Many people think blogs are to make money but they really aren’t. A blog is a great way to learn some online skills, get your words out there and meet new people but they are one of the worst ways to make money. The best way to use a blog is as a marketing tool either for yourself or for the particular business your running but it isn’t a business in itself.

I’ve also learned to bootstrap. There are countless stories of people starting businesses for less than $100. The faster you can bring in money the better. Start with whom you know that you think would benefit from your business and approach them first. See if people are willing to buy it and improve it from there.

8. When did you know that you were not only a travel addict, but also an aficionado? How did you begin packaging your own traveling experiences as hacks with value for your online community, the Canadian Free Flyers?

Canadian Free Flyers is a travel hacking membership site. I had learned about travel hacking from some American bloggers and began earning thousands of miles. As I got more involved, I realized that there was a real lack of Canadian deals being featured on travel hacking sites and decided to niche down and start a my own site just for Canadians. This allows me to focus on Canadian deals only and to fill a gap that wasn’t being served.

In terms of being a travel addict, I just found myself thinking about travel all the time. I love the thought of new places to see, new sights, new smells, new tastes, and new cultures. I love being on an airplane and getting off an airplane in what feels like a completely different world. I love how each travel experience opens my mind more and teaches me things that I could never learn from a book or a classroom.

9. What’s your process for choosing your next adventure? How much planning goes into it, and how much spontaneity do you allow?

When I first began, I didn’t do any planning at all. I still remember showing up in Indonesia solo a few years ago without realizing I needed a visa. Luckily, you can just buy them at the airport but it was stupid not to know that in advance. I didn’t even know what Bali was but I found the cheapest guesthouse I could and just started meeting other travellers who shared activities and friendship.

Since then, I’ve definitely become a better planner but I don’t like planning too much. Because I occasionally participate in media visits, I do have to do more planning to coordinate different activities and organize a time for me to go.

Matt2Other than that, I tend to focus first on countries that really interest me, jump on Google and just start reading a little bit about what they’re like, what the different seasons bring, what the general cost of getting around is and what are some of the top things to do. I ask friends or bloggers that have been there or reach out to locals I’ve met in other countries. I also like to look on the UNESCO World Heritage Site and see what amazing sites the country has.

While all this research helps me find the amazing sites of a country, I also like to leave a lot of room for spontaneity and for the little things that really make a trip special. The planning just gives me an idea of where to go but it’s the little things like the friendly chats at restaurants, the new people I meet and the locals that really find a place in my heart. For example, we arrived on the remote island of Flores in Indonesia with the purpose of visiting a beautiful volcano but on arrival we made friends with one of the guys and we were invited to a big wedding. That was such a special experience and not something you could plan. However, the planning for the volcano is what got us there. I don’t think heavy planning is important but I do think it is important to be open to changing plans when new things arise. If you follow a pre-determined plan for your whole trip, you’re losing the magic of travel and you might as well just join a tour.

10. Has creating an online community changed the way you pursue experiences or perhaps reflect on them? What about having a life partner—what have you learned about traveling together?

I definitely find I’m a lot more insightful. When I’m travelling or trying new things or meeting up with friends, I find I think deeper about situations and pull a lot more out of them. A lot of this has to do with writing. By sitting down to extract my thoughts onto the blog, it’s now transformed my brain into doing that on the spot. I also tend to see if there’s anything I’m learning that others could benefit from.

Matt4It’s pretty amazing to be able to travel the world with my wife and share the experiences. When it comes to my solo trip to Australia and New Zealand, a lot of it is just in my head. I have amazing memories of it but with all the travel since then, I can actually share the memory with my wife and relive the experience just a little by talking about it. While I do occasionally miss the solo adventures, I couldn’t have found a better travel partner. She’s open to adventure, trying new things, meeting people, expanding our mindsets and visiting “third-world” countries. If she was someone who only travelled to 5-star locations, I don’t think it would work out.

I’ve certainly learned that there needs to be a balance. While I might be gung-ho to do a 4-day hike every week, she might not be. It can’t all be about me now. We need to balance each other’s wants and needs. Luckily, she is pretty much in-line with me so it works out quite easily.

Budgeting is certainly different, as almost everything becomes twice the price. Like most relationships, it all comes down to communications, understanding and cooperation.

For those considering travelling a partner they haven’t lived with before, just remember that you will now be spending 24 hours together. It can be a good way to test a relationship but it’s smart to know what you’re getting into.

11. Of all the exhilarating things you’ve done, which experiences have been the most rewarding, the most affirming of your values and purpose?

That’s a tough question. Bungy-jumping stands out as a moment when I truly felt invincible. It’s an activity I never imagined I would do and accomplishing something so terrifying really changed my character. Since then, I’ve felt a lot more confident in challenging any fears I have. Scuba diving is another activity that has changed my life. It’s another activity I didn’t imagine myself doing. It just seemed like an activity for more daring people but jumping in the water with an oxygen tank on my back has changed my life. I’ve always loved sharks and being able to swim right next to them has not only broadened my perspective of the prehistoric predator but has also made me realize how misunderstood they really are. They’re quite graceful. Aside from sharks, just being able to witness life under the sea is like being on another planet. It’s just incredible to be amongst this unique ecosystem and watch the different fish interact with each other. Throw in giant sea turtles, seals, whale sharks, dolphins and giant schools of fish and you can see why this has become one of my favorite activities.

Another rewarding experience was volunteering at La Senda Verde animal refuge in Bolivia earlier this year. Volunteering is something I’ve always wanted to do but didn’t find the time for. My wife and I made sure to set aside two weeks to volunteer in Bolivia and it was also a life-changing experience. Not only was it rewarding to work with Monkeys, Parrots, turtles and other exotic animals but it was also rewarding to meet the owners, who have basically dedicated their entire lives to provide a healthy home for these helpless animals who were kidnapped from their own habitat. Without this refuge, these animals would be confined to a cage in someone’s home or dead. It was so incredibly inspiring to see people willing to dedicate their entire life for the well-being of animals. Truly heart warming.

On a less “adventurous” note, my blog has also been a life-changing project. It has introduced me to new people and new activities and whenever I get an email from someone who was inspired to change their life, my heart lights up. What better feeling than to know I made a positive difference in another’s life. It’s also contributed to my entrepreneurial endeavors because it gave me a place to practice and a place to express myself as well as a catalyst for meeting other bloggers and entrepreneurs.

There’s really so much I could say for a question like this. I had some local teenagers in Myanmar buy me a beer because I sat down to hear them play guitar at night. A beer is the price of two-days wages and they bought me a beer. I offered to pay it back and they wouldn’t accept. I couldn’t believe they would work so hard and then give me (someone who obviously had more money) a beer. I almost cried. Their generosity moved me into a place of gratitude. Then, in the Philippine’s, our tuk-tuk driver invited us over for dinner with his family. We ate a delicious and simple dinner from their floor. They had no table but they had chairs. Again, they obviously has much less than us and yet they were willing to share. How inspiring is that?

It’s moments like these that truly drive me to travel independently and to go to places that are not very touristy. These are the experiences that are magical.

Thank YOU Matt for sharing your wisdom and insights

Matthew G. Bailey is a blogger, online entrepreneur, and world traveler. He is creating a movement at – a site dedicated to helping you push your limits and creating a world of excitement, adventure, and endless possibilities. He also teaches Canadians how to travel around the world for next to nuthing at You can also find him o Twitter @MatthewGBailey


Tal Gur is a world traveler and personal development enthusiast. An adventurer at heart, after trading his daily grind for a life of his own daring design, Tal spent a decade pursuing 100 major life goals around the globe. His journey continues as a location-independent blogger, lifestyle entrepreneur, and coach. Tal’s published two books: One Year to Freedom, a 1-Year Roadmap to Living Life on Your Own Terms; and, his most recent book and bestseller, The Art of Fully Living – 1 Man, 10 Years, 100 Life Goals Around the World.

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