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! 


About Jessica

Jessica Dawdy is a Canadian freelance writer who is slowly working her way around the world. She has lived in seven different countries across Europe and Asia, feeding her ever-expanding appetite for food, culture and languages.

40 Responses to What’s on for 2014: Go Big or Go Home

  1. Stef January 22, 2014 at 5:54 am #

    I wish you all the best. I can totally understand that you're terrified but I agree with you, if you never try you'll never know.
    My recent post What to eat and drink in Argentina

  2. Teresa January 22, 2014 at 6:22 am #

    Good luck!

  3. Steph (@20YH) January 22, 2014 at 8:40 am #

    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

  4. Remi January 22, 2014 at 9:09 am #

    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.

  5. Muriel Savoyat January 22, 2014 at 10:45 am #

    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

  6. Colleen Brynn January 22, 2014 at 11:39 am #

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

  7. ferretingoutthefun January 23, 2014 at 10:44 am #

    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

  8. Julika January 26, 2014 at 5:43 am #

    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!

  9. Mig January 27, 2014 at 8:37 am #

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

  10. The Guy January 27, 2014 at 8:47 am #

    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

  11. sarah January 27, 2014 at 12:18 pm #

    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!!

  12. sarahwriteshere2010 January 27, 2014 at 10:07 pm #

    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.

  13. sarahwriteshere2010 January 27, 2014 at 10:08 pm #

    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.

  14. Olivia Oyster January 27, 2014 at 11:11 pm #

    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

  15. Mike Vogler January 28, 2014 at 9:35 pm #

    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

  16. Gia January 29, 2014 at 1:06 pm #

    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

  17. Beth January 30, 2014 at 4:08 am #

    Congrats on the big move Jess! I'm also hoping to make that jump come summertime.

    Also, I'll be in Chiang Mai in April for Songkran, so if you're around… let's organize a big blogger meet up 🙂
    My recent post 20 Common Chinese New Year Phrases (And How to Pronounce Them!)

  18. @OddYearsTravel January 30, 2014 at 11:42 pm #

    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

  19. Erika January 31, 2014 at 2:26 pm #

    Good luck with the transition! I'll look forward to reading about your new life in Thailand–a pace that has long stood at the top of my list!
    My recent post On Development and Tourism in Namibia and Lesotho

  20. TammyOnTheMove February 1, 2014 at 12:55 pm #

    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!!!

  21. Tricia February 5, 2014 at 11:55 am #

    Good luck on transfering to a full time freelancer and your Thailand move.
    My recent post Heading to Alaska

  22. Agness February 16, 2014 at 7:54 pm #

    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

  23. adam February 17, 2014 at 7:21 pm #

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

  24. malaysianmeanders March 1, 2014 at 10:01 am #

    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

  25. where is istanbul November 11, 2015 at 5:47 pm #

    I love this picture. I enjoy when I read 🙂

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