How We Created Our Own Luck

“Wow, you guys are so lucky to be able to travel the world.”

We’ve heard a lot of people say this to us and while they are absolutely right that our lifestyle is amazing and we get to experience some truly wonderful things, it’s not luck which has brought us to where we are now.

Although we are very fortunate to be having the sort of adventures that we are having, we haven’t arrived here by pure luck. It has been a series of “what ifs”, “why nots” and life-changing decisions which have brought us to where we are now.

Decisions that seemed crazy and foolish at the time have since proven to be the best choices we have ever made. It has turned out to be a case of “fortune favors the brave” as we have rejected the conventional path which was laid out for us and made several choices which have led to our digital nomad lifestyle.

There have been many little decisions which have added up to our current lifestyle, but here are four of the biggest pivotal moments in our journey so far.

Deciding to Go Traveling in the First Place

Way back in 2009, Lee was in England and I was in Canada and although we had not met each other yet we already had something in common.

We both had great jobs that we loved, our own apartments, a good wage, a fun social life and what would conventionally be considered a successful existence. However, we also had something else in common and that was a deep curiosity about the world and a burning desire to see what else was out there.

That’s why we both saved up our money, quit our jobs, applied for working holiday visas and booked our tickets to New Zealand. We ended up meeting while we were working for accommodation at Napier Prison, a creepy old abandoned prison turned tourist attraction overlooking the ocean on the North Island. It’s not surprising that Lee and I had such an immediate connection, we both shared the same dream of traveling the world even though we were from different sides of it.

Kelly and Lee in New Zealand
Kelly and Lee in New Zealand

Making the decision to go traveling can be an incredibly amazing experience, because it can open you up to the possibility of your life being completely transformed. Once you step away from everything that is familiar, you will find yourself meeting new types of people, exposed to new ideas and having experiences that can totally change the way you see the world.

Deciding to Take a Chance on a Travel Romance

It’s one thing to have a travel romance in New Zealand with another backpacker, but it’s another thing completely to go back home to their home country with them after having only known them for a few months.

Lee and I had only know each other for three months and been a couple for about a month when he had to go back to England. We both knew that we were onto a good thing but we didn’t know what the future would bring. When he suggested that I come back to England with him, my heart leaped for joy.

It must have seemed like a crazy decision from the outside. I had spent all my money traveling around New Zealand and was struggling to find a job, so I had to borrow some money from my parents to get to the UK. We were a brand new couple it was a big risk. What if things didn’t work out?

Strangely though, it was the easiest decision I have ever made. Although it was scary to take a risk on a new relationship, a new country and a new life, I love Lee and I trust him. For some reason I knew everything would work out fine. I also knew that if I didn’t take this chance now, I would always regret it.

A cup of tea on a chilly morning at Accrington Stanley's football pitch, March 2010
A cup of tea on a chilly morning at Accrington Stanley’s football pitch, March 2010

So I applied for my UK working holiday visa and booked on the same flight as Lee, adding on what turned out to be a 14 month detour in Accrington to my six months in New Zealand.

Writing for Pennies

From very early on in our relationship, Lee and I had started scheming up ways that we could make money while traveling the world. We often talked about how a freelance career online would be the perfect way to do this, as it would give us the freedom to move about as we pleased.

However, I didn’t become a successful freelance writer overnight. I found myself starting out with the small, low paying, un-fulfilling gigs which many people would consider a waste of time. I took on many arduous and head-ache inducing writing assignments which ended up paying less than minimum wage. In the beginning, this was all the work I was able to obtain and after a few months it became quite tiring. However, persisting with this type of work meant that my freelance portfolio and my credibility on online freelance job boards could be established.

Before too long, my rate rose sharply and I found myself forming a serious freelance writing venture.

I had to slog through the hard work first, before I could afford to make this hammock my office
I had to slog through the hard work first, before I could afford to make this hammock my office

Some people might have given up or thought that some of the low-paying jobs were beneath them and a waste of time, however the contacts that I was building were much more valuable than the poor compensation would suggest.

Committing to the Digital Nomad Lifestyle

After a year in England, we had a secure, successful lifestyle again. We had lots of money flowing in, a house and a great social life. Essentially, we were back where we were at the beginning of this story, except together as a couple. Of course, this is when the wanderlust started again and we began to ask each other that question, “What if?”

The decision to go traveling in New Zealand was one that didn’t quite work out financially. It left me in debt and Lee ended up spending all of his money. However, since we had built up a successful freelance writing business and a travel blog, we realized that going on another travel adventure didn’t have to be so much of a financial risk this time. We could continue to make money on the road while fulfilling our dreams of exploring the world.

So we gave away and sold everything we owned except for what we could fit in our backpacks and hit the highway. That was 18 months ago and we have been exploring the world ever since.

Kayaking in the Jungles of Malaysian Borneo
Kayaking in the Jungles of Malaysian Borneo

The one thing in common with all of these life changing decisions was that there were many sensible reasons not to make them. They may have even seemed foolish at the time.

However, the other thing that they all had in common was that they were all what we wanted to do. We didn’t let obstacles such as money, circumstance, or uncertainty get in the way of our goals. Of course, this isn’t to say that we haven’t had a lot of help along the way. There are many people who we are very grateful to for supporting our decisions and helping us on our journey.

While it hasn’t always gone exactly to plan, the life we have now is a direct result of these big decisions. Although we are fortunate to life the live we lead, it’s not all down to luck.

Have you ever made a big decision that changed your life? Share your stories with us in the comments!

Kelly Dunning

A Canadian freelance writer with a love of art, culture, literature and adventure, Kelly loves exploring foreign lands and expressing her experiences through the power of the written word.

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  1. This is a really inspirational post and one which has got me thinking. I have spent a lot of time building up my blog, but never with the intention of supporting myself online. Now I am thinking that I should go for it. How did you get the small freelance jobs that got you started?

    1. Thanks, glad you enjoyed the post!
      Starting up an online income is a great way to be able to have the freedom to move around at your own pace and travel as much as you want. It takes a while to build it up, so be patient, stick with it and put yourself out there!
      When I first started freelance writing I used You make a profile and then search for writing jobs, then submit your bid for them. I got lots of my early work from that website.
      You can also use, and many others. Whenever you make a successful bid and complete a job, the employer gives you feedback on your profile which can help you get the next job. There are so many different writing gigs on there, some big and some small, so you are sure to find something.
      Let me know if you have any more questions about it! Good luck and have fun. πŸ™‚

  2. i earnestly congratulate both of you, it seems like you were created for each other, usually this is do not occur in all relationship. Now, that I am too old to travel, but I still like to wander alone in the Himalayan jungles, not at the places which are spoiled by tourists, the places, which appealed no body, the virgin places. You can always live longer if you have passion and a company who nourishes it.
    Visit India, you will keep writing for years.

  3. I’d like to double Runaway Brit’s comment…I’ve been working on my blog all the time without much thinking of freelance writing or even much guest posts on other blogs, though I have read about their importance many times. maybe it’s time to actually do it now πŸ™‚

    One thing I have to oppose (which I argued a lot about it on my blog) is that still luck played in the background of your story…if both of you were from non european, non canadian or US or australian countries, say, middle easterners like myself, you would still not be able to travel freely for so long, or at least not to wherever you wish you can travel.

    1. Hi Mina,

      You bring up a very important point here. The problem with luck is that it is very relative term. I would not argue with somebody from a less fortunate background than myself If they said I was lucky, but the people we hear this from are often other westerners. People with incomes sometimes higher than our own and people with much higher lifestyle related expenses. πŸ™‚

  4. Kelly, I could not agree with your post more. You have to create your own luck to live the dream of travel and a location independent lifestyle. The most important thing, like you said, is to make the first step on deciding to travel. I have just done so myself! I agree that once you step away from the familar a whole new life emerges; new friends, new horizons. Great Post!

  5. Hi great post, and very well written, hope you enthuse many people to undertake the same, whatever path to online income they take.
    Amused that you didn’t mention taking out a huge mortgage as even in Australia where property so far has held up, this invokes great controversy (‘ you will miss out on the property ladder’ etc etc. ) I guess real estate has fallen over the last few years so probably not so much of an issue. maybe people cannot go as they have negative equity – or it is harder to go.
    You didn’t mention Tin Ferris book, 4 hour workweek, this has been an inspiration to many.

    1. Not really sure what your point is on property. We do not want one at the moment because the expense would stop us from being able to travel as freely. As for Tim Ferris, he is a very successful writer but we don;’t really share a lot of his more extreme attitudes.

      1. Dear Lee
        I think I didn’t make myself clear, my point on property was that lots of people get themselves into large debt with property and get trapped, and you have been smart enough not to do that. Regarding Tim Ferris , not sure what of his more extreme attitudes are, but his encouragement for people to take charge of their future, be entrepeneurs and free themselves from jobs many aren’t happy in, is to be applauded. I think you journey seems in this vein. (No aspersions on your previous jobs intended.) Cheers Ben

  6. Really enjoying your blog. My wife and I dropped everything and moved to Japan and love every minute of it. I still lead a “normal” life here, though, and I really admire your adventures. Maybe some day we will follow suit.

    Meanwhile get in touch if you ever want to borrow an apartment in Chiba Japan.

    1. Thank’s Oliver, We may just take you up on that if we are ever in the area πŸ™‚

      Really glad you are enjoying Japan, It’s always great when a big decision pays off.

  7. Interesting that you say luck played no role, yet you were lucky enough to be able to rely on your parents in your time of need. For most people, that’s not a feasible option. You were also lucky enough to be born in commonwealth countries, where you can very easily obtain work visas for other countries (such as your original trip to NZ and Kelly’s subsequent move to England). Those aren’t things you worked for or created, you lucked into them. You guys are great, but your whole premise here is just dishonest.

    1. Hi Bradley,

      Thanks for your comment. I will definitely agree with you about the fact that our countries of origin make it a lot easier for us to travel. It was easier for us to get working holiday visas because of this. But this doesn’t make our “premise dishonest”.

      The point we are making is not about the situation that we started in, it was the choices that we made. The point of the article is about designing your own ideal situation by making conscious choices. That can be applied to whatever situation you start off in.

      If my parents had not lent me the money, I would have found it from some other source. If that hadn’t been an option, we would have found another solution.

      We have heard the whole “you are so lucky” spiel from a lot of people and most of them are people from the US, Canada, the UK and Europe who have all of the rights and freedoms that we do and often a higher income and more money than us. We wrote this article to dispel some myths about the traveling lifestyle and to share our story.

      If we had been from different countries, we would have been different people and this would be a completely different story. If I had been from Iran and Lee from North Korea or something like that, we probably wouldn’t have met and if we had, it would have been a different story which has no relation to this one.

      I don’t really think you have a point. It’s almost like you are saying, “But you guys have two arms and two legs, you didn’t work to create that you just lucked into them.” We are not trying to take credit for where we were born, which of course we had no control over. We recognize that we are two people who have a lot of rights and freedoms in the world, but this article is not about that. It is about the decisions we made afterwards and where they got us.

      What exactly is dishonest about that?

  8. Great blog, have enjoyed your writing style. I believe you have made your luck, and the most of opportunities that have come your way, good for you. πŸ™‚

  9. Kelly and Lee,

    This is so awesome that you guys are able to do this. You’ve inspired us to try to think outside the box when it comes to balancing work and travel all at once.

  10. I’m going to read and re-read this until I find the same courage you all have. Traveling just a few times a year is hardly enough…not for my gypsy soul, at least. Thank you!

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