State Of The Dropout

It’s a bit over six months since I quit my job in Singapore and dropped out of the rat race for a more relaxed life in northern Thailand.

Not much has gone to plan since the big dropout, my second supposedly-more-planned-and-adult exit from my career.

I left Singapore with a promise of part-time work and plans to build a location independent copy writing business. The plan was to spend six month building the business and then take it on the road, to Provence in France and Delft in Holland, where we’d organised non-simultaneous home exchanges.

I had visions, as you do, of our six months in Thailand involving a lot of lolling on a hammock tapping away at my laptop, baby gamboling (quietly and non-destructively) at my feet, while Darling Man did vigorous and bare-chested things in the garden. I had visions of strolling through wet markets greeting the vendors, of exploring ancient temples and zipping into Myanmar for the weekend. I had plans to start every day with a yoga class so I could regain my youthful glow (and no longer be asked if I was Miss M’s grandmother).

But 17 days into the dropout, my father died and we rushed back to Australia. It was a completely unexpected and devastating event, one that left me floundering for months. I was an emotional wreck, unable to concentrate on anything, completely obsessed with the unfairness of life and the brutal silent swiftness of death.

The flights home also blew an enormous hole in our savings. And it turned out we weren’t insured for this kind of thing, even though I thought we were.

When we returned to Thailand, I kept putting off the yoga and the business-building plan. I did a bit of work here and there but I didn’t market the business at all. We ate through a bit more of our savings because the promise of part-time work remained a promise for many months. Even though I knew agreeing to work for a start-up could involve delays, those delays were a bit frustrating.

In the end, without really making a conscious decision, I became a part-time remote editor, rather than a location independent entrepreneur. I chose to wait for the start-up to get started rather than start my own business.

In some ways I’m a bit disappointed with this outcome. But I think in some ways, at this stage in life, with a young child, it is easier for me to be an employee. I have been working predictable hours for an hourly rate of pay. When asked to take on other projects, I don’t even know how to estimate how much time the work will take. I’ve undercharged every time. For me, entrepreneurialism is a burden I just can’t handle at the moment. But … I’m going to give it another try after our European adventure.

The slightly underhand part of my dropout plan also failed. Darling Man did not fall in love with Chiang Mai or the concept of location independence. The past six months just made him more homesick for Vietnam, his friends and the career he put on hold for me two years ago. So we will set up a new home base in Ho Chi Minh City in July so he can resume his life. Miss M and I will still do as much travel as possible, with Darling Man joining us whenever he can (or wants to).

The last six months have been a blur of grief and work and quite a bit of worry. And worrying was NOT supposed to be part of this dropout plan. I had to work many more hours than I expected to make sure we had enough money for the Europe adventure. And most of the work came in in the last few months, resulting in a bit of a mad scramble.

Our six months in Thailand has been a wonderful family time. I have had much more time with Miss M, who, at two and a half, can no longer really be called a baby. I have loved watching her learn to talk and explore the world.

When we arrived in Chiang Mai, Miss M’s absolute priority was lurching towards danger. Now, I find her much more manageable. She regards so many things interesting, such as talking, jumping, singing, pointing at things, standing in the rice cooker, putting her feet on the table and ripping pages out of books.

We are leaving Thailand with less savings than when we arrived. But we manage to rebuild from the alarming dip in our bank account after our trip home to Australia. We did, sadly, miss a dear friend’s wedding because we couldn’t afford it. But despite the leanish times, we lived very comfortably in Chiang Mai, in our furnished three-bedroom house, eating out often and becoming regulars at our local market.

Our Chiang Mai house

Reflecting on the lessons of the last six months, I realise:

  • freelance writing follows something very similar to Boyles Law, with the amount of time required to finish the work expanding to fit the available time.
  • paid-by-the-hour editing work is easy to walk away from. When the work is done, it’s done.
  • computers should not be used to decompress from a day of working at the computer.
  • life should be enjoyed, not endured, because you don’t know how long you’ve got.
  • worrying about money doesn’t actually make you any more money, it just makes you crabby.
  • two-year-olds are hilarious.
  • paying someone to do the housework is a great investment, if only in terms of the arguments over housework that are avoided.
  • I may have forgotten Western table manners (which is not going to make me popular in Europe).
  • you never ever, no matter how much you try, can completely convey how much you love someone. But you don’t realise this until they’re gone.
  • the fact that I spent time on this blog rather than doing some paid jobs is a big hint that I may have found my passion.
  • Thai food is wonderful – and much easier to cook than I expected.
  • I have a weird obsession with Buddhist monks.
  • as well as being smart, funny and handsome, Darling Man is the most incredibly patient man and the best father a little girl could dream of.

At the end of this six-month experiment, I think I have proved a number of things.

First, location independent work is possible. I am quietly proud that I have managed to support my family for six months, and fund a European adventure for us. Even though it is going to be a super-budget European adventure.

Second, traveling with a toddler is possible. Sometimes it’s even fun. A 16-hour train ride with a toddler is infinitely more tiring than a 16-hour train journey without a toddler.

Traveling with a toddler

Thirdly, although I call myself a career dropout, if I hadn’t spent so many years dedicated to my career, I don’t think I would have been able to pull off my crazy plan. I took a huge risk, quitting my career again. But I was able to draw on skills I developed over many years. The path I’ve taken is not for everyone, but it is possible.

I hope you’ll continue to follow us on our next adventure. Stay tuned for more food, family and travel fun as Miss M and I set off for Europe. Hopefully Darling Man will get the Schengen visa he needs so he can join us in a few weeks.

Blog posts may not be as regular as in the past while I’m a solo mum, so please be patient with me.

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11 years ago

By: Barbara

A career girl who dropped out, traveled, found love, and never got around to going home again. Now wrangling a cross-cultural relationship and two third culture kids.


  1. Laura says:

    Good luck with your upcoming adventures in Europe. Things in life never seem to go as planned, but somehow it sounds like it’s working out for you 🙂
    Laura recently posted..Two Stops in San Francisco

  2. Hi Barbara,

    I love posts like this. It’s the stuff we’re thinking about – how do I make this kind of lifestyle work for me? What happens when things don’t go to plan? What if something goes wrong with someone I love at home?

    Thanks for being so honest about the difficulties of being a dropout. Life’s not wonderful all of the time but it’s good to hear you’re coming out the other side of your grief and making changes to your lifestyle so that it works for you. I’m sure it would be a lot more difficult going all of these without your DM and baby girl by your side. Being a dropout at least gives you the time and space to deal with your emotions.

    Look forward to hearing how your European adventure goes.

    Bethaney – Flashpacker Family recently posted..Planning for Thailand, Malaysia & Singapore – Four Days to Go

    • Barbara says:

      Thanks Bethaney, you are right about life not being wonderful all the time. We have had some wonderful moments, and DM and Miss M make life even more wonderful!

  3. Sally says:

    It’s possible I’m a little bit selfishly happy to find out that you’ll be settling in Vietnam. I still have yet to get there (soon! maybe! I swear!), so it’s definitely on my must-go list. It’s nice to know that if and when I eventually get there, we might be able to finally meet!
    I enjoyed reading your list of things you’ve learned. I’m also going through a big transition right now. I’m quitting my job (again!) and have been worrying about money and my next job and all that other stuff. But, like you, I think if I didn’t have my career behind me I wouldn’t be able to quit my job with the confidence that something will turn up for me.
    Best of luck in Europe! I look forward to reading about your adventures there.
    Sally recently posted..Stuff I Really Kind of Like About My Life in China: My VPN

    • Barbara says:

      You have to come visit us in Vietnam! You can be a guinea pig for the street food tours we are thinking of doing.

      Good luck with your big move. I hope something FANTASTIC turns up for you, Sally.

  4. Life is so two steps forward, one step back, but what you’ve done is remarkable. Look forward to reading the next chapter…

  5. A lot of great life lessons learned in the past 6 months. A good reminder that things may not always work out exactly as we planned, but we can still get something out of it and recognize the successes.

    Enjoy your European adventure. Looking forward to reading about it.
    Stephanie – The Travel Chica recently posted..Cafayate: Wine, Wine, Wine! (part 2)

  6. flipnomad says:

    things dont always go as plan but things happen for a reason… despite all of the setbacks im sure that the entire experience is a great learning curve for you 🙂

    take care and keep the passion burning… im sure everything will fall into its right place in time…

    and i hear ya… this kind of lifestyle is not a walk in the park… but its fun 🙂
    flipnomad recently posted..Meet the Nomads – Barbara of The Dropout Diaries

  7. two year olds ARE hilarious. and yes, life does have twists and turns that we can’t even imagine. i am always glad for love, family, and friends – they see us through! brava!
    wandering educators recently posted..Homemade tortillas

  8. Leigh says:

    There is no predicting the ups and downs and life but it’s always interesting to see the lessons they teach us and how they influence the direction of our life.
    Good luck with your move to Vietnam and hats off to you traveling with a toddler.
    Leigh recently posted..The Beauty of a Visit to Glenbow Ranch Provincial Park

  9. Turkey's For Life says:

    Great post Barbara and very brave, too. It’s so easy to write about making the difficult decisions to give it all up to do what you love and everything will be great. We all know real life doesn’t always work like that. So happy you’re continuing along this route though. Like you, we’re hardly rolling in cash but we make the most of what we’ve got and we’re happy with it that way. 🙂

  10. LIfe is so unpredictable. I think it’s great you’re doing what you’re doing despite the year you’ve had. I look forward to reading the rest of your inspirational adventure!
    21st Century Mummy recently posted..Listography – 5 wishes for my children

  11. Heather says:

    I relate to so many of the things you’ve written here. I’m also a career drop-out, location-independent writer who gave up everything to move to a foreign country. I also prefer blogging over paid work. I’ve also recently experienced the sudden death of someone I loved beyond measure, forcing me to re-examine my already very confusing life. The only difference is that I live in Africa and I don’t have a Darling Man or a toddler 🙂

    I have a lot of respect for what you’re doing. Congratulations on making it work so far. Wishing you all the best in the next phase.
    Heather recently posted..A Bryanston Shopping Spree

  12. Michi says:

    I’m so sorry to hear about your father. I can’t imagine having to go through something like that… I’d be an emotional mess, too.

    I love coming back and reading your updates, I don’t think any other blogger has made me laugh and tear up at the same time. Your endurance is remarkable. I’m hoping that everything works out for you and your lovely family.

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