“Suddenly, I wasn’t afraid of anything. I was so confident in myself.” Read Matt’s leap story below…

Please share your story… what was your leap?

You know, it was tough deciding what leap I wanted to share. There have been many over the last 9 years. Big and small. But as I sat here thinking about it, I’d like to talk about the leap I took back in 2009. That was the year I finally decided to travel solo. The year I decided to take a dream trip by myself and fly to Australia and New Zealand for 6 months.

I had been talking about going to Australia for more than five years at that point. I don’t know why I was obsessed with Australia and I don’t know why I left it that long. In the beginning, I had planned to go with a friend. But as most of us probably know, waiting for friends (especially for such a long trip) is a sure-fire way to never go. I then went to college, started learning about real estate investing and as they say, life got in the way.

What inspired you to take this leap?

I think it was a combination of two things. I had just finished reading the first edition of the 4-hour Work Week by Tim Ferriss. Although it definitely rekindled my entrepreneurial roots I had as a kid, it did more to rekindle my passion for seeing the world. Tim touched on traveling alone and his writing was like a kick to the A#$. The other inspiration came from realizing how many years it had been since I first mentioned going to Australia. I realized that if I didn’t do this for myself, it was never going to happen. I couldn’t wait any longer for others to join me. I just needed to go, no matter what.

After reading that book, I became extremely determined to make some changed in my life. It was now the spring of 2008. I had already bought a condo before my 23rd birthday and I had just finished buying another rental house. It seemed like I was doing stuff that would inhibit me from travel. My parents told me they were flying to the east coast of Canada to visit family and I decided I wanted to test out solo travel. I quit my job, asked a friend to help me manage the tenants and then booked a ticket to meet my family in Newfoundland, but not before spending a week solo in Boston, MA. I don’t know why I chose Boston but it sounded like a cool place to check out. It was my first experience couchsurfing. It was my first experience traveling alone.

I’m happy to say that it was simply awesome. I met some locals there who invited me to stay with them. I would go out and explore by day and hang out with them all night. I had the most amazing time ever. That encouraged me to continue with my dreams of visiting Australia by myself.

What is it that made this a leap for you?

It was going to be my first time traveling alone and I would be doing it for 6 months on the other side of the world. I had real estate to look after back home, a girlfriend in Mexico and a job.

Traveling alone sounded kind of exciting but kind of scary. It’s often hard for people to put themselves in that vulnerable of a position with that kind of independence.

Eventually, the exciting part of it won.

How long would you say you thought about taking this leap before you did it?

We’ll, it was about 7 years in the making, although it’s not like I thought about it every day. I know I must have talked about it a lot when I was 18 years old because my girlfriend at the time had bought me a book about Australia. This was 2002.

Then the big kick came in 2007 when I read the 4-hour work week. After that, I started to get more involved in travel and the idea of traveling solo. Let’s just say I got more serious.

I finally boarded the plane in February of 2009.

If you thought about it for a while first, what changed that allowed you to take action?

I began to realize how many years had gone by without me taking action. I started to think a lot about how quick life can fly by and before you know it, you’ve missed out on all the things you dreamed of doing.

I didn’t want that to happen. I knew that if I continued to wait for people to join me on my adventures, my dreams would never happen. I made a decision from that day forward, that I would do what I wanted to do, whether I had someone to join me or not.

There is no scarier thought to me than sitting on my death bed wishing I had done things different. Wishing I had lived a life I wanted to live.

What was the hardest part before you took the leap? Was anything challenging after you did it?

You know, the hardest part was the real estate I had just purchased. I don’t know what I was thinking. Real estate is probably the worst investment that someone who wants to travel can make. I think I got sucked into the major boom that was happening and the thought of financing my travels with property. This didn’t happen at all and it actually made parts of my trip very stressful.

It’s amazing how I could go from being very passive to the idea of traveling alone to being so determined that I was willing to leave $800,000 worth of real estate behind on the hope that everything would be okay.

The main challenges once I left was real estate and occasional loneliness. Things ended up not going so smooth with the properties and many parts of my trip were spent on the phone with lawyers and banks. Skype isn’t the best for serious matters like this.

I met a ton of cool people to spend time with as well but there were still bouts of loneliness now and then. Most of this came from the fact that I had met a girl at university just before coming and I was missing her as well. I even went to Mexico City for a week before going overseas so that I could meet her family and show her I was still serious, despite the big trip I was about to take. As mentioned before, I wasn’t letting anything stop me from making this trip.

It was tough to go with all of these new things in my life but I knew if I didn’t, the excuses would keep piling up.

(FYI: I’m getting married to that same girl in 2014).

How did you keep yourself motivated to stick with the change as it was happening?

In this case, it had a lot to do with proving to myself that I could do it. Once you begin traveling solo and experiencing the wonderful experiences that come about, the fear sheds away and everything begins to look like an opportunity for adventure. The beautiful scenery around me helped as well.

What was the best part of the experience?

Realizing true independence and adventure. After making such a big trip alone despite all the problems happening at home with tenants and banks and all that stuff, I knew I was ready to tackle anything. I was never going to let things stand in the way of my dreams again. From there-on-out, I knew that whatever I wanted to do, I would find a way.

The realization of solo travel is very liberating. It was like a big door opened up in my life. I no longer needed someone to come with me. The obstacle was gone. If I wanted to go somewhere, I would just book the flight and go.

That’s an amazing power to have.

Looking back at the leap you made, is there anything you’d do differently if you were doing it again?

Well, for one, I wouldn’t complicate matters further by buying something as location-dependent as real estate. That’s a huge burden to carry on your shoulders when you’re on the other side of the world.

Second, I would put greater thought into the aspect of the trip and not make such a rushed decision without first taking care of important matters. Although I’m happy I let nothing hold me back, I would take a smarter approach from now on. For example, if I did have real estate, I would make sure everything is in order as much as possible in hopes of avoiding headaches while traveling.

For another example (especially now with all the hype on being a digital nomad), If you’re someone who is thinking of working online, I would think hard about that before you go. If you don’t have a solid business that’s bringing in money, I would focus on the trip instead of a business. You don’t want to waste a potential once-in-a-lifetime opportunity by sitting in front of computers thinking of ways to make money. Just save up and enjoy the trip as much as you can or develop a successful business before you go.

What did you learn about yourself from taking this leap? About the world around you, if anything?

I learned how adventurous I was. Although the solo trip seemed like a big enough leap, I took much bigger leaps once I got there. I ended up sky-diving in Southern New Zealand, Bungy-jumping off the Auckland Bridge, hang-gliding off Byron Bay in Australia and scuba diving next to sharks on Great Barrier Reef.

I never would have imagined me doing these sorts of things but after doing one, I gained more confidence for the second.

Suddenly, I felt so comfortable throwing myself into all sorts of situations. I even jumped into a car with strangers and travelling for three weeks down the sunshine coast of Australia.

Suddenly, I wasn’t afraid of anything. I was so confident in myself.

I also learned that the world is a beautiful and welcoming place. It’s easy to meet new friends and have fun. The opportunities are endless.

I learned how independent I really am. It was like I became a new person. Like nothing could hold me back.

If you had to describe what making this leap has done for you in one sentence, what would you say?

It changed my life by giving me a new mindset. A new way of looking at things.

Is there anything else you want to share about your experience?

While in Australia, I decided on a whim to go to Bali, Indonesia. Again, I was doing this alone and it was my first time in Asia. I didn’t plan anything. I didn’t even know about visas. I was just full of adventure and ready to jump into anything. This was also a life-changing experience and I might not have done it if not for the initial leap to go to Australia as well as all the adventures I jumped into.

If there is something you dream to do, you must do it. You must not put it off any longer. Yesterday is gone, today is a gift and tomorrow is uncertain. It doesn’t matter whether it’s big or small. If you’ve always thought that being a dancer would be cool, join a salsa class. If you think it would be amazing to speak in public, join toastmasters. If you dream of traveling somewhere, go. Start planning now and leave within the year.

If it’s something big like travel and that is super scary, start by doing small things to break your comfort zone. As I mentioned take a dance class. Join a travellers group and meet people who have done what you want to do. Join toastmasters and speak in front of people. Take a short 3-7 day solo trip somewhere. Make new friends at a random event. Go whitewater rafting.

Do something uncomfortable. Build your confidence up.

But whatever you do, don’t put off your dreams for the perfect time. There is no perfect time. All time is perfect because “this time” is the only time that is guaranteed.

Matthew Bailey is a world-traveling entrepreneur, writer, travel hacker and nature lover. You can find him at LiveLimitless.net, where he writes about personal development, travel and entrepreneurship. He also teaches Canadians how to travel around the world for – almost – free at CanadianFreeFlyers.com. He has been featured in the Toronto Star as well as the Vancouver Observer. His bio can be found at MatthewGBailey.com.

Matthew G. Bailey
Adventure traveler, Explorer, Writer, Entrepreneur & Maximalist
Push Your Limits with Live Limitless
Learn how to fly for free at Canadian Free Flyers
Tweet me: @MatthewGBailey
Learn more: www.MatthewGBailey.com