Matthew Bailey: Live Limitless

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Matthew B.

This week’s interview is with Matthew Bailey, online Entrepreneur, Podcaster and Blogger. Matthew is an incredible Goal Achiever who used to be a cubicle working, real estate investing 23-year old business graduate surrounded by six-figure jobs. Life could have been comfortable but he decided to leave it all and live limitless. He began his life of adventure by trying new things close to home. Anything he found interesting and made him uncomfortable. Matthew believes you don’t have to follow the path that others follow. You can indeed create your own. You can design your own world.

The Achievers Story

Tell us who you are, where you’re from and something that people would find interesting about you? 


My name is Matthew Bailey and I’m originally from a small town in northern Alberta, Canada called Fort McMurray. It used to be about 25,000 people, but due to the oil industry, it’s growing fast. However, when I turned 20, I realized it wasn’t for me. It’s a strange place now because everyone (even teenagers) can make $100K per year with very little (or no) education. This brings with it a lot of people who move to the city just for money, which also brings a culture of parties, drugs, and materialism. It was a great place to grow up but as I got older, I realized I didn’t want to get suck in the system so young. I didn’t want to be part of it. I wanted to explore the world and myself but I had no idea what to do. My only rational decision at the time was to move to Calgary, a bigger city 8 hours south.


Give us a brief overview about the goal you achieved and why it was so important?


The goal was to find myself and be more active in trying new things. After moving to Calgary, I started doing anything that sounded interesting to me. I took a 12 week public speaking course from the Dale Carnegie foundation, enrolled in a salsa dance class, acted in movies, and tried out for the Olympic speed skating team. Eventually, I ended up taking my first long term trip to Australia. Since then, I’ve developed a love for travel and writing as well as many other passions and interests.  


Every story has a beginning, middle, and an end; where we’ve been, where we’re going, and everything in between. Give us an example of what your life was like before achieving this goal?


It was boring! Everyone worked passionless jobs and went out partying on the weekends. There didn’t seem to be any real passion for life other than making money, buying things, and getting drunk. I wanted to be the person who tried something new. I always  wondered what life was like outside of that little town and dreamed of doing more with my life.


Help us understand what caused you to move in a different direction?


The realization that I’m not getting any younger. I started to imagine myself at retirement age and all the “what if’s” I might have in my life.


Give us an example of what your life is like today, since achieving the goal?


It’s a lot more adventurous and exciting. There’s a lot more possibilities and opportunities. For the last five years, I’ve been very focused on travel and entrepreneurship. My wife and I usually spend 6 or 7 months in other countries each year, which has been very life changing. I feel like I’ve earned multiple Phd’s in life. I’ve experienced so many cultures and have truly been able to see life from many different angles. I’ve made friends with people around the world and have also created blogs and businesses online that help people travel the world or make their life better.

Overcoming The Obstacles

If there’s one thing I know for sure it’s that obstacles like fear, time and money among other things can prevent us from or motivate us towards achieving goals. What are the top 3 obstacles you faced, why were they obstacles to begin with, and how were they conquered?


One of the bigger obstacles was my mindset. I always found myself waiting for other people to join me. My first solo backpacking trip to Australia and New Zealand was one of the things that changed my life the most. It was one of those things I had been waiting 6 years to do because I was waiting for someone to go with me. I finally realized that if I kept waiting for someone else it would never happen. I decided to go alone.


Time was another obstacle. I was always trying to find the perfect time to do stuff and ended up putting things off. Eventually, I realized that we don’t ever get more time. You have to make the time and commit to achieve your goals.


The third obstacle was money and it relates to mindset as well. People think you need a lot of money to travel for a year or more, but one of the things I learned was that it’s a lot cheaper than you might think. There are tons of people who travel around the world for $20 a day. You just have to get out there and do it.

The Triumph

The next part of the interview is the Triumph. The triumph is all about taking the success of achievement to the next level of personal greatness. The idea of greatness can be different for everyone. For me, greatness is all about the pursuit rather than the destination. What does greatness mean to you and how has achieving this goal contributed to that idea? 


For me greatness is really digging down deep to find out what you want in life and then going after it. When I was younger, my goal in life was just a reflection of what I thought success was. I wanted a big house and a shiny sports car. Now that I’ve experienced life on an all-new level, my dreams have changed. You really have to dig down because the last thing you want to do is chase the wrong dream.

Roadmap To Goal Achievement

What is the best advice you ever received that helped you clarify and/or achieve this goal?


I’m not sure that there is any single piece of advice. I still remember reading the Tipping Point by Malcolm Gladwell. I think that was one of the first books I ever read. I wasn’t much of a reader. There was something about that book and reaching a tipping point that really inspired me to start doing creative projects.


The 4 Hour Work Week by Tim Ferris inspired me to look at life in a different way. It taught me to look at obstacles in a different way and that there was a new way to be an entrepreneur. Tim also recommended a book called Vagabonding, which inspired me in a deep way towards life and mindset.


What are some of the resources or tools that helped you achieve this goal?


Reading was big for me. Whether it was blogs or books, I tried to surround myself with people doing what I wanted to do. After traveling throughout Australia, New Zealand and Southeast Asia, I also developed a passion for travel hacking, which enabled me to travel more by making flights very cheap or even free. Travel hacking is finding creative ways to earn frequent flyer miles and redeem them for trips all over the world.


What did you do to stay motivated throughout the process?


A lot of it was trying to visualize the outcome. I would think of the worst outcome, which is never that bad. I would also imagine my life at the end of the road and what I would tell myself at this moment.


Is there a book that helped you achieve this goal? If so, how?


The Tipping Point by Malcolm Gladwell – I always joke that this was my tipping point into the book world so that one really inspired me to create projects but also to read more


The 4-Hour Workweek by Tim Ferriss – the last book that really inspired me toward traveling


Vagabonding by Rolf Potts – a book recommended in the 4 Hour Work Week. It’s an amazing book not only for those who want to travel, but really understand the mindset of a traveler


What blogs and podcasts do you recommend?


The 4 Hour Blog & Podcast 

Chris Guillebeau The Art of Non-Conformity 

James Altucher Podcast

The Unmistakable Creative Podcast  


If you were advising someone on how to achieve the same goal or something similar, what specific steps would you have them follow?


Develop a plan and surround yourself with people who are doing things that are exciting. Don’t be afraid to reach out to people and get help.


What’s the best way for people to connect with you?


Live Limitless

Canadian Free Flyers

Zero to Dream Trip


Is there anything else you would like to share before we conclude?  


Live Limitless! Take the time to envision yourself in retirement and think about what you would need to do now in order to make yourself happy and satisfied at that point in your life. Life is short and you only get one chance.

Blake Lea

Blake Lea

Blake Lea is a content creator, traveler, and entrepreneur. He's the owner and founder of Goals Are Cool.

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Goals Are Cool was created to help inspire, motivate, and prepare people to achieve their goals in both life & business. Start living your best life today!

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