From the Predictable 9-5 to 500+ Days Traveling the World: Troy and Dorene’s Inspiring Transformation Story

From the Predictable 9-5 to 500+ Days Traveling the World: Troy and Dorene’s Inspiring Transformation Story


Do you have a long-held dream? Have you fantasized about a new reality day after day, month after month, year after year only to realize that all you’re left with is just that: a fantasy?

And how many times have you uttered the phrase “one day” (code for: probably never!) when speaking about your ambitions, goals, desires and big dreams?

Troy and Dorene, a married couple from Toronto, Canada were in this boat for more than a decade. They had a 10-year dream of traveling the world, but in reality: zero traction, zero action, and plenty of frustration.

Instead, they spent 15+ years building successful careers and lives and each year would maximize their bleak number of vacation days by taking a month-long trip to gain a deeper, more meaningful travel experience. In their 40’s, they had comfortable, safe and predictable lives. Yet there was a deep yearning to move away from what was expected of them, toward a dream that was calling.

So what does it really take to turn a long-held “one day” dream into reality? And how did Troy and Dorene start to turn things around? What made the difference? And what was the one powerful step that they took to set the rest in motion? How did they go from their day-to-day lives in Canada to recently notching up more than 500 days on the road?!

This week, join us as we interview Troy and Dorene about what it really took to finally fulfill that yearning. But before we dive into our incredibly fired-up conversation, first a little bit more about their story…

Trading in Things for Experiences

In 2015 Troy and Dorene sold everything they owned—the house, the beloved vespa, furniture, and all of their possessions—and paid down all their debts, to hit the road full time and embark on a personal mission to reinvent their lives through travel. They have since built a successful business called Travel Life Experiences.

They have created a life where experiences define them, not a company or job title, and now they get to show others why none of what they do is actually about the travel itself, it’s about the personal journey they’ve experienced along the way.

But it certainly wasn’t always this way…

Dorene: I was a senior marketing and advertising director in the entertainment, food and drink business. Climbing the corporate ladder was all that mattered to me. I felt stuck in my career—I enjoyed the work, and working with my staff and teams, but each year all the hard work never allowed me to see through the efforts my team and I created. Each year, there would be another company reorganization—new sales targets, more short-term profits and short-term thinking. And often it was at the expense of laying off staff.

I got bitter about these business ways, I lost my willingness to be creative and I lost my positive attitude (which I was known for at work and inspired others). I had the blinders on—too busy doing rather than thinking and just being. I lost perspective—and in the end I lost my job because I stopped supporting the company line.

Troy: I spent 20 years in the television broadcasting industry, the last 10 as a freelance editor and producer. I loved to create and I really enjoyed my job. I had a great 20-year career but I was no longer fulfilled. For most of my career I’d worked on other people’s projects, but I found myself wanting to create and work on my own projects.

The TV industry was going through some major changes and for the first time in 20 years, the question of  job security was staring me in the face. I was struggling with that “What’s next?” question. I didn’t know. I was constantly reading inspirational blogs and listening to podcasts about changing your life but never acted. I craved to take my life in a new direction.


In 2014, Troy took one small step that set the dominoes in motion to realizing his and his wife’s dream of taking a year off to travel the world.

He joined Live Your Legend’s How to Connect With Anyone (CWA) course, and one of the first tasks was to write up a personal bio and answer the question “What are you creating/building?”

While he had no clue what he was “building” he wrote down: In 2015, we will take a year off to travel.

No huge fan fare, no big deal, and certainly no plan of how to make that a reality! But that tiny step set in motion a set of events that has to be heard to be believed!

We hope you enjoy our conversation and discover why we believe travel is by far the biggest accelerator for change – and how meaningful experiences (as opposed to “escape” or package deal travel) can truly awaken something profound inside of you:

Live Your Legend: Travel Life Experiences Transformation Story from Live Your Legend on Vimeo.
Don’t see a video? Click here. Looking for Audio Only? Download here.

Pretty amazing story huh?!

Here are some highlights describing their incredible journey over the past few years…

Life before LYL

Back then, a typical day for Troy included: Wake up and go to work. Come home from work. Make dinner or go out for dinner. Spend the rest of the evening in front of the TV… Repeat.  

The only difference for Dorene was working (usually from 7am to 7pm), exhausted and spent when Troy got home, only to answer emails from the day! They were waiting for the next thing to excite them—usually it was their travel plans somewhere. They were living on autopilot…

The Wake Up Call

Dorene: I lost my job and when I started working I was completely uninspired by the work, I was back in a businesses that focused on short-term profits and thought: “Is this all I’m good for? Is this it?” At the same time I was going through that, I saw Troy making some big changes personally—and he was getting very inspired…

Troy: There wasn’t really one specific event that led me here—it was a series of events over the course of 4 months. When CWA started, and over the next few months, I began connecting with new people, making new friends and going to local meetups in Toronto. The one thing that stood out to me were the conversations—they were different. Everyone you talked to in this community was building something, working on their passion project and so we all rallied around each other, supporting our projects. There was never any negativity in these meetings; it was all about helping each other. I was loving it because I finally had a passion project and now I had a community of people that wanted to help.

The LYL Advantage

LYL helped in every way. From the courses that got us believing we could do it, to getting us to ACT, to connecting with people we never could have imagined, to becoming members of the Toronto LYL community—we see LYL as a major component in helping us through every step we made to create our change.

It was really interesting. When we made our decision and talked about what we were doing, it made us even more open, and more willing to help others in the group with their goals. And eventually we became hosts of the Toronto LYL meetups!

The tools that helped them the most were:

How to Connect with Anyone—Back in August of 2013 Troy watched an interview with Jonathan Fields and Scott Dinsmore:

This was my first time ever hearing about Scott and what he was all about. When he started talking about helping people find the work they love it really grabbed my attention. So I Googled him and that led me to his TEDx talk and then his Live Your Legend website where I immediately signed up for his How To Connect With Anyone course.

Live Your Legend Local

We attended most of the meetings in 2014. We were very active both as attendees and as hosts. Even though a lot of people came and went each month, there was a core group that always showed up. Over the course of the year these relationships grew into friendships. The support and encouragement we got from the friends had and still have a lasting impact in everything we do.

Free weekly articles

The tips each week helped us to stay inspired and to think about particular topics differently. Consistently, every week, we are inspired by reading something from the blog.

Live Off Your Passion Guided Discovery

We did this course with two other people in Toronto. Every few weeks we would get together and go through the modules and assignments together.

Bumps in the Road

Live Your Legend: Troy and Dorene Transformation Story

Big, painful challenge #1: Getting on the same page with timing

Figuring out when we were going to take the leap to start our own business and redesign our lives and do it by living location independent was our biggest hurdle. We talked about making changes in our lives for 10 years. Troy was ready years earlier, Dorene was ready once we did the RevU course and started to brainstorm one night in a hotel room in Cuenca.

We overcame it by the steps that Troy took with LYL to opening himself up to conversations and people, and later I joined in on the LYL sessions.

Big, painful challenge #2: Imposter syndrome

We didn’t think we had the “voice” people wanted to hear. We didn’t feel we were expert enough. But we just started posting, putting our voice out there and we quickly realized people wanted to listen.

Big, painful challenge #3: Managing the change

This was the first time we’d ever really worked together. We have very different personalities and very different work styles. The challenge was balancing our strengths and figuring how to communicate without p*ssing the other off! The big thing was giving each other feedback.

Getting past this we first had to learn how not to speak to each other. Knowing when was a good time and when was a bad time made all the difference in the world. Now we are very conscious of this and communicate much better.

Big, painful challenge #4: The last days of leaving our house

Live Your Legend: Troy and Dorene Transformation StoryIt had nothing to do with the decisions we made or any attachment to the house, we were past that. We were just exhausted! Everything over the last few months took its toll on us. I think it was because we were so close to realizing our dream we were scared that something would happen that would pull it out from underneath us.

The last day of moving out of our house we got a phone call. Dorene’s Dad was in an accident. It was bad. He was in a coma for 10 days, and eventually passed away from his injuries, exactly 30 days from when we were leaving.

Legendary Wins

We now have a new lifestyle—living location independent and traveling around the world. We started a blog and business—Travel Life Experiences—where we help people who feel stuck and that they are missing out on life (like we were). We inspire people with our videos, stories and tips to make changes in their lives, to be more aware of themselves and the world—to create a more fulfilling life.

We also do freelance marketing/video work and create travel videos and storytelling for travel companies and brands. We can’t believe we created this amazing life—and we’ve never looked back!

Live Your Legend: Troy and Dorene Transformation Story

A huge thanks to Troy and Dorene for sharing their story! And we can’t wait to hear from more of you out there making your unique imprint on the world!

Here’s to believing in yourself and lifting up those around you!

Connect with Troy and Dorene and learn more here:

And for the comments… Troy and Dorene are happy to answer your questions, so please post some good ones below!

– The Live Your Legend Team