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What’s on for 2014: Go Big or Go Home

Posted By in Expat Life, Freelancing and Location Indepedence, Travel Musings | 40 comments

What’s on for 2014: Go Big or Go Home

What are we doing in 2014? It’s a question that’s had dozens of different answers over the past 6 months: Spend a second year in Japan, teach in another country, move back to Canada, or maybe give house sitting a long-awaited try.

The decision ended up forming much in the same way our decision to leave Canada came about over 2 years ago. We were sitting in a bar, talking not about what was safe, but about what we really wanted for ourselves.

More than anything, we both want to be part of a community again. I’ve alluded to our isolated home bases occasionally on this blog, but the full truth is that Brent and I have been feeling increasingly lonely. Our work exchanges were lonely, and our teaching positions have been lonely. We’ve met some wonderful travelers in passing, but after a while, the pattern of meeting people, forming quick friendships, and then saying goodbye a day or 2 later is exhausting and unsatisfying.

live in thailand

It also became clear that we needed to revisit the main reason why we started this trip: Freedom. We succeeded in leaving Canada, but we’ve yet to succeed at becoming truly free. We’ve lived in 7 different countries over the last 28 months, but we’ve always traveled based on volunteer exchanges or jobs – we’ve always been locked into something. We never stopped having a schedule, fixed vacation periods, and exasperating employers. In many ways, our time has been no more our own than it was when we were living in Canada. Every evening when Brent and I put aside our own projects and haul ourselves into the company car to drive to our classes, I feel like I’m still comprising what I really want for the sake of stability.

So when we sat down to ask ourselves what was next, we began to realize that the answer was not another job or another fixed arrangement. So: We’re moving to Chiang Mai, Thailand.

live in thailand


Over the last few months, I’ve been taking on more and more freelance writing and editing projects. And I love it. I love picking and choosing the projects that interest me and setting my own schedule. It’s the flexibility and freedom I’ve always wanted – the antidote to why I’ve always been a little bit frustrated with every salaried job I’ve ever had. So, I’m going to freelance full-time. That might even still involve some teaching, but we’ll find our own private students and do it on our terms.

live in chiang mai thailand

Chiang Mai, 2012

If you read other travel blogs, then the reasons why we’re choosing Chiang Mai as the place to do this are probably obvious. Chiang Mai offers (almost) Western standards of living at half the Western costs, amazing food, fast Wi-Fi, and a thriving expat population of bloggers, entrepreneurs and digital nomads. It’s true that there was a time when I couldn’t wait to get out of Thailand, but Chiang Mai couldn’t be more different from the dead-end town where we spent 10 months teaching. If we’re going to make a relatively ballsy move like this one, there’s some modicum of comfort in at least doing it in a country where we already feel at home. Plus, if we can make it work in Chiang Mai, then we’ll have the confidence and resources to go just about anywhere afterwards.

live in thailand

Am I terrified? Totally. The next few months might be a colossal success or gigantic failure, but at least I’ll know if I’m capable of being self-employed. The only way to find out is by throwing my hat over the fence, diving into the deep end, and embracing a whole bunch of other metaphors for fully committing.

For now, this move also means refocusing on what this blog is all about: Travel – throughout Thailand, SE Asia and everywhere else.

Have you been to/lived in Chiang Mai? What do think of our plan? Are you planning to be in SE Asia over the next 8 months – let’s meet up! 



  1. Teresa January 22, 2014

    Good luck!

  2. Steph (@20YH) January 22, 2014

    Jess, this is so exciting for you! I never would have guessed that you would be heading back to Thailand as I remember when you left that you did so for good reason. But I think CM will be a perfect place for you to start this next chapter of your life and I'm really excited to see where this new adventure takes you. We've been basing ourselves in Vietnam to do something similar, the idea being that it's one of the cheapest places on earth for us to work… if we can't support ourselves while we're here, there's no way we can make it anywhere else!

    We have no immediate plans to return back to Thailand, but who knows… maybe when our three month visa is up here, we'll find ourselves in your neck of the woods! Would love to meet up if things happen to shake out that way!
    My recent post Marvelous, Magnificent Mulu

    • waysofwanderers January 22, 2014

      Very cool! I'm so glad you guys are going for it too. The plan is to explore parts of SE Asia we missed during our last trip, including Vietnam – so I'm sure we'll meet up one way or another!

  3. Remi January 22, 2014

    I’m glad you’re choosing self-employment and freelance work to finance your new way of life ! It’s a great move and I will keep talking to my friends and contacts about your writting skills. I wish you bith great success in this new endeavour.

  4. Muriel Savoyat January 22, 2014

    Gold luck !
    We wish you all the best for these project and we hope we can go to Chiang Mai and see you. 😉
    Muriel et Gilles

    • waysofwanderers January 22, 2014

      I hope you'll visit us too! If all goes well, we might get another AirBnB rental started :).

  5. Colleen Brynn January 22, 2014

    I definitely have good feelings about this. You will do great. Sending you some good vibes for the big move. All the best!

  6. ferretingoutthefun January 23, 2014

    How exciting!! I fell in love with Chiang Mai when we visited and could easily see myself living there for a while. Good for you for figuring out what you want and making it happen! Our adventures are taking us to Europe next, but if we tire of the cold winter weather you might find us in your neck of the woods. Good luck with the move!
    My recent post The Royal Palace of Gödöllő, Hungary

    • waysofwanderers January 23, 2014

      Same here! We only spent a few days there last time we were in Thailand, but I loved the vibe of the city. I'm looking forward to keeping up with your Europe travels.

  7. Julika January 26, 2014

    What a brave decision to start a whole new lifestyle abroad! Wishing you the best of luck with everything! I can't wait to read all about the big move and your new life as a freelancer!

  8. Mig January 27, 2014

    Congrats on your move to Thailand! I've been reading around the web that many digital nomads have made that home base. Best wishes!

  9. The Guy January 27, 2014

    Congratulations on deciding on your next long stay home. With a wonderful climate and cheap cost of living it should be a great place to be. Although will you still have the same issue of short term friendships?

    Best of luck with the freelancing. Being your own boss sounds like a great way to be.
    My recent post Guangzhou Must See – China Stopover Points

    • waysofwanderers January 27, 2014

      Thanks! Perhaps the friendship thing may still be an issue – although my impression that although people are constantly coming and going from Chiang Mai, there are always people who stick around for a little longer. We'll definitely have to wait and see, though.

  10. sarah January 27, 2014

    Sounds like a great plan. It's great news for us too as we are considering a similar plan late in 2014 after we leave Central America. SEA is top of out list of places to base ourselves for a while and work on our online business but we have zero experience there. We'll be following your travels and hopefully borrowing some tips!_Best of luck!!

    • waysofwanderers January 27, 2014

      Very cool! Here's hoping we'll be an example of what TO DO and not what NOT TO DO :).

  11. sarahwriteshere2010 January 27, 2014

    There was a moment when I was reading this post where I was like "I wonder how long that flight is, maybe I'll go visit Jess in Thailand" and then all the other parts of my brain were like "What in the heck are you thinking? Are you trying to kill us?"

    I've never willingly considered travel before. Your blog is having an impact on me.

  12. sarahwriteshere2010 January 27, 2014

    I take it back! Oh oh oh I take it back! I just looked it up the flight is 15 hours long.
    I'd never recover. Please write more and I will pretend I'm there.

    • waysofwanderers January 28, 2014

      You could take a break halfway. Spend a week in Italy? Do it. Then I'll take you to a ping pong show and you'll have ample blog content for months.

  13. Olivia Oyster January 27, 2014

    Best of luck with the new plans and freelancing. It is great to be your own boss but you also need self-discipline to make your own routine. In some ways, you will still need to be on a schedule, but it'll be more rewarding because it's on your own terms!
    My recent post Camping with Kangaroos

    • waysofwanderers January 28, 2014

      Definitely! I'm already working harder and longer than I have at any job, but it's worth it to be my own boss.

  14. Mike Vogler January 28, 2014

    I've never been to Thailand but wow I've heard a lot about Chiang Mai, Jessica. Some friends of mine were there just a week ago on tour. I wish you all of the best of luck and you should do great! The freelance writing on the side sounds fantastic 🙂
    My recent post Phoenix’s Trip To The Dog Grooomer, A Flashback

  15. Gia January 29, 2014

    Hi there!! Found your blog thru nomadic Matt. I’m a new blogger/independent traveler who just started both journeys :p I am currently in India. Thanks for the resources. Also I am planning to make it to Thailand this year so I do hope you’ll be happy and settled and we can meet. 🙂 many blessings ~ gia

    • waysofwanderers January 29, 2014

      Thanks for stopping by! I bet India is amazing! I so want to go there! Let me know when you're in Thailand :).

  16. @OddYearsTravel January 30, 2014

    This is a really honest and touching piece. Not everyone can pinpoint their problems and take the plunge to make their lives better like you are doing. You two are courageous. Good luck in Chiang Mai!
    My recent post Anuradhapura, Sri Lanka – Photos

  17. TammyOnTheMove February 1, 2014

    I am so excited for you guys! I have never been to Chiang Mai, but it seems the perfect place to try out something new. And with all the other bloggers out there I am sure you can get the odd tip from them as well. Good luck!!!

    • waysofwanderers February 1, 2014

      Thanks, Tammy! I'm excited to read about your travels in S. America this year :).

  18. Agness February 16, 2014

    Well, well… I see someone's moving from Japan to Thailand. Great decision! Chang Mai is amazing and I always wanted to participate in lantern festival there, but never managed to make it there. Such a pitty! Wishing you all the best and can't wait to read more about your Thai life :). P.S. I miss Thai food a lot these days!!!!
    My recent post Leuven, Belgium Under €25 A Day

    • waysofwanderers February 17, 2014

      Thanks! And I agree, I've definitely been missing Thai food since we left!

  19. adam February 17, 2014

    Chiang Mai is a great place to spend a few months!

  20. malaysianmeanders March 1, 2014

    I've only spent a week in Chiang Mai, during the hot season no less, and completely enjoyed it. I think I really liked that I could get Tex-Mex there. I've had other friends who have lived there and had tons of good things to say about expat life there. Good luck!
    My recent post Running Around Beijing's Olympic Green

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