A Breakup Letter

January 4, 2012 | Article, Travel | 58 Comments

Dear Big Corporate World,

It’s over.

I think we’ve both known it for a while, but the time has finally come to call it a day.

Our relationship hasn’t been great for a long time now. Sure, it started off well – but I think most relationships do, you know? I was young and naive, and you just seemed so important and sophisticated.

I’ll admit I was seduced by your promises and your power. You took me places I’d never been. Flying me around in the pointy end of aeroplanes, staying in five star hotels, paying for expensive meals. You showered me with gifts and made me feel special. For a kid who grew up in small town New Zealand without much money, you really were a dream come true.

For the first few years we were pretty happy together. Sometimes you were a bit overbearing and possessive, sure, but I just thought that was the way our sort of relationship worked.

It did upset me when you told me I couldn’t go out with my friends at night or on weekends because you needed me so much, but I got used to it eventually. You told me what we were doing together was really important, and I believed you.

It took a long time for the cracks to start showing. When once I’d looked forward to seeing you every day, I ended up resenting having to spend so much time with you. The shiny things I got from you started to look a lot more like bribes — and all of a sudden they just didn’t make me happy any more.

Slowly but surely, I began to feel crushed. I was exhausted from having to spend so much time keeping up appearances for the sake of our relationship, pretending to be someone I no longer was. I couldn’t remember the last time you’d made me feel genuinely happy, or I had done something that really inspired me instead of just what you told me to do.

I knew that things were getting bad when I stopped feeling committed to you. I’ll admit it, my eyes started to wander. Other people seemed to be happy in their relationships, though — why wasn’t I? I tried all sorts of things to make us work, but eventually I just couldn’t hide it any more.

It’s not you, it’s me. You know we’ve tried to break up more than once in the last few years. I left you for a few months back in 2008, remember? I needed a break and even though I came back to you eventually, we both knew it was the beginning of the end.

So then there was last year. I walked out on you again in January, and had never been happier. For ages I loved my newly single status, and when I grudgingly agreed to try to make us work one last time on a trial basis, my heart just wasn’t in it.

And now we’re done.

I’m in Thailand these days, and it’s amazing. There are so many people here who have broken up from toxic relationships just like ours. We’re our own little support group really — except we don’t seem to need any support! I’ve never been around such a positive and happy bunch of people.

I think this single life really suits me.

This time I’m not coming back.


All the best for the future,


Image via WoodleyWonderworks


2012: building, travel and a question
The Friday Photo #90 – Shellfish on the rocks


  1. Reply

    Cole @ Four Jandals

    January 4, 2012

    Awesome Dave. Keep it up and hopefully we will follow in your jandal-steps soon.

  2. Reply


    January 4, 2012


  3. Reply

    Lisa Wood

    January 4, 2012

    Now that is the best breakup letter I have ever read :)


  4. Reply


    January 4, 2012

  5. Reply

    Paul / MyPostcardFrom

    January 4, 2012


  6. Reply

    Lisa - NZ

    January 5, 2012

    This is the letter that I'm in the process of writing for myself. I'm in the midst of planning a breakup within the next 12-18 months. I'm just starting to go through the process of working out what will fill the gap though..... Very inspiring!

  7. Reply

    Mica of

    January 5, 2012

    Keep it up! :D

  8. Reply

    Kim and Duane

    January 5, 2012

    Awesome! This is priceless :)

  9. Reply


    January 5, 2012

    Love love!

  10. Reply

    Bobbi Lee Hitchon

    January 5, 2012

    haha this is amazing!! glad you got out of your sour relationship. the corporate world never treated you right anyway.

  11. Reply


    January 5, 2012

    This is great! Sometimes breaking up isn't so hard to do after all:) I'll be in Thailand for all of February and into March. Will you still be around?

    • Reply


      January 6, 2012

      Sure will be - no plans to leave here before mid April at the earliest :) Come say hi!

  12. Reply


    January 6, 2012

    Fantastic! Myself, I'm hoping never to enter into a relationship with the corporate world.

  13. Reply

    Matthew Needham

    January 6, 2012

    Dave, absolutely brilliant. I really admire you. I left Corporate employment in 2008 and have never been happier!

  14. Reply

    Congrats on following your bliss!!!

  15. Reply


    January 7, 2012

    Here here! Found this post through Torre's twitter, and certainly glad I did. Glad you're following a path that's right for you, it inspires me to find my own, keep it up! :)

  16. Reply


    January 7, 2012

    Oh, to someday write this letter myself...

  17. Reply


    January 7, 2012

    Dave I think this is the breakup letter that everyone wants to write one day. Good on you for having the courage to do it.

  18. Reply


    January 8, 2012


  19. Reply


    January 8, 2012

    Congrats! Enjoy your newly found freedom :)

  20. Reply

    Gerard ~ GQ trippin

    January 8, 2012

    Man I can relate to this... Luckily my job quit me before I quit it. Now it's RTW time. :)

  21. Reply


    January 9, 2012

    I can't imagine going back. I know that Shaun and I have to go back to work and save again but I can't imagine the cubicle anymore. It would be soul crushing. Love the post!

  22. Reply

    Nomad Heather

    January 9, 2012

    Hilarious! I can't wait to break up with my job next year.

  23. Reply

    Leslie (Downtown Traveler)

    January 9, 2012

    Kudos for leaving the grind! What's next for you?

  24. Reply

    Zablon Mukuba

    January 9, 2012

    congratulations on your break up!!! enjoy your life as a back packer

  25. Reply


    January 9, 2012

    love it!

  26. Reply


    January 10, 2012

    Wow, what a letter! I missed the "Dear Big Corporate World" line up top and at first I thought this was to an ex... Very powerful stuff :)

    Also, I've read several posts, and for some reason I had thought until now you were American... I'm American, so I probably just assumed. Anyway, random thought to share.

    • Reply


      January 10, 2012

      Thanks Liz, glad you enjoyed it! And nope, definitely a Kiwi ... my passport even says so ;-)

  27. Reply

    Marina K. Villatoro

    January 10, 2012

    Congratulations! It's so not easy to do and I'm sure you've been going nutty on the inside, but it's the best thing in the world.

    Have fun.

  28. Reply

    Tricia Foster

    January 11, 2012

    Thank you Dave! I just went through the same break up on Dec 7, 2011. I can relate to every word. Even though I have no savings, and I am not really sure what will happen next, I feel my life is finally starting to align with the priorities of my soul. Your letter gives me hope and inspiration.

  29. Reply

    Shirlene from Idelish

    January 16, 2012

    Congratulations on taking this big leap! Looking forward to reading more about your adventures!

  30. Reply

    wandering educators

    January 16, 2012

    bravo, dave!! i am excited to follow your journey, online. you can do it!

  31. Reply

    paul | walkflypinoy

    January 21, 2012

    thoroughly enjoyed this post. serioulsy! well done, dave. well done. :D

  32. Reply

    young teaser

    January 25, 2012

    wow i love this post...........well done Dave i amso proud of u.well deone

  33. Reply


    June 17, 2012

    Wow I just read the post and You said it so eloquently and I was in the same boat...My boat just took me to start my own business...I think it is something that has to come from the heart..I have to say that its not for everyone ...

  34. Reply


    July 17, 2012

    Wow! You are so brave! Amazing..

  35. Reply

    Chrystal McKay

    August 13, 2012

    So charming and funny. Love this letter.

  36. Reply

    obedy ochora

    September 29, 2012


  37. Reply


    October 9, 2012

    Great post :) And the corporate world is brilliant for one primary purpose - to make some cash which usually entails trying to provide for a family or at the very least, paying back monstrous student loan debt. I appreciated it for what it was, and felt fortunate to have spent the time I did working decent paying jobs - especially as I was the single Mom to a young child at the time.

    Think of it as just a step on your journey that helped you get to where you are now. When I left I knew one thing... make that two:

    1. I wouldn't be missed.
    2. There was someone out there to take my spot who maybe needed it more than I

    :) Lots of us have been there, best of luck on your continued journey, Molly

  38. Reply

    Tracey - Life Changing Year

    November 6, 2012

    Oh this made me giggle. Then it made me panic! I'm about to start the reconciliation process! Is it really not going to work? Maybe I'll just save the hassle and stay broken-up!!

    • Reply


      November 6, 2012

      Well I can say that it's working pretty well for me so far... ;-)

  39. Reply


    November 8, 2012

    Ok - I'm just adding to all the comments that praise how funny and clever (and true) this is.

    It's good to hear you're feeling much happier. Sometimes I've wondered if people who are unhappy at home will still feel unhappy when they're traveling. Great that it has worked for you.

    I'm also from Christchurch.

    • Reply


      November 8, 2012

      Thanks! And I think you're right, I do meet people who traded their misery at home for a different kind of misery on the road. I guess that I was fortunate - I'd tried to leave the cubicle, at least temporarily, several times before so I was pretty sure that was what I wanted...

  40. Reply


    January 25, 2013

    This is brilliant. I am awaiting the day until I can do the same... I did a similar thing, I left my soul-crushing NYC corporate job once before back in 2009 when I moved to Breckenridge, Colorado for 1 1/2 years. Wound up coming back, immediately recognize my error and hatched a 3 year plan (about 18 months ago) so I can shed this lifestyle for good...

    I'm just about to FINALLY pay off ALL my debt ($1,500 left of $30k+) about 2 months behind schedule and am ready to swing the pendulum into a nice savings account.

    In the mean time.. patience, patience, patience.

    Well done dave... and great site btw!!

  41. Reply


    April 3, 2013

    Hi Dave,

    Stumbled upon your blog on LinkedIn, and I love it. I can really relate and am curious to read more of your posts.
    This one is funny, although I have never had a truly well-paying corporate job, I've had some office jobs that I could have written a similar post about.
    I actually wrote very similar break-up post in 2010, a letter to New Zealand. Since you're a Kiwi I thought you might enjoy it. For the record, I was broke when I left NZ, and looking back now I do really love the country :).

    Right, back to reading your blog!


    • Reply


      April 4, 2013

      Hey Elsbeth,

      Glad you're enjoying the blog! And as someone who has "permanently" left New Zealand three times now, I can totally understand the sentiment of your post! My time back there recently definitely made me love the place again ... but I still can't see me settling down there again long term.

      Then again, I'm not sure I can see myself doing that anywhere. ;-)

  42. Reply


    May 22, 2013

    Totally feeling you, loved the breakup letter. Continue writing and safe travels.

  43. Reply


    July 3, 2013

    This is a really clever way to do this! I enjoy how you point out that work is not everything in life and that you have a relationship with your job. Everything is a choice, and just because something works for someone doesn't mean it will work for someone else. Nicely put.

  44. Reply

    Overwhelmed by all the awesome comments, but Dave, I feel you! I literally have to tell my boss by Friday whether I'm committing for the next year...or not. And not, leaves me room to go travel! Thanks for this creative touch :)

  45. Reply


    April 17, 2015

    Wow, Dave. Beautiful. Bravo!

  46. Reply


    December 16, 2015

    Dave, though it's been a while since your break up, congrats!! :D I had the same break up years ago and never looked back, and I've been so much happier since, just like you. I even got tattoos on the tops of my wrists to remind me to never go back (I would be told to cover my tats for work, so putting them in plain sight reminds me why I left in the first place).

    Thanks again and I love your blog and writing. I'm heading out on my biggest adventure yet, backpacking the UK and Europe long-term in May of 2016 at 39 years old and I can't wait, and your blog just inspires me more towards doing that. I'm also a writer and can't wait to start sharing my journeys and adventures. Speaking of which, congrats to your girlfriend (and you as I'm sure you helped her with it somewhere along the way) on her book being published!! Much love and happiness!

    Wesa :)

  47. Reply

    Keir Briscoe

    January 19, 2016

    I went through a similar breakup just last year. I'm really happy I skipped the rebound and was not tempted by any other quick contracts. The experience has left me a bit jaded. I keep urging all my friends to breakup as well. I may even be getting through to some of them. Especially when the see the photos of the awesome time I just had in New Zealand.

    My goal is to never have a real job again in my life. I may return to Canada again in the future but at this point I really don't think about it.

    Thanks for all the great reads on this blog. Im looking forward to reading more!

  48. Reply

    Jason, London - UK

    January 21, 2016

    Hi Dave, brilliant break up letter. I thought I could satisfy my backpacking with 2 weeks in Australia after Christmas, I haven't been back in 8 years after my WHV.

    I couldn't really make friends because of such a short time away! I went from 94F to 28F when landing in London, UK oh I felt it. I was due in work the same day as landing. Corporate job in finance its served me well the last 11 years and financed my travels, brought me nice things, and even offered me a job after my WHV (and while I was away) so they will again...

    Now I find it boring! It booked my trip to Aus very last minute, and loved the freedom. I talked to some people, but nothing really lasting. It kinda hurt leaving these people I hardly got to know!

    So tomorrow/today, my cars on eBay/Auto Trader and my watch is being valued! Then save, save, save! You've inspired me to leave. I read a book, by John Green - Paper Towns. There is a quote " It is so hard to leave—until you leave. And then it is the easiest goddamned thing in the world" I read this in Berlin last year and being in Australia has cemented it for me. It will be a cold few months, but Christmas in NZ - Lake Tekapo or NY in Sydney will make it all worth it! Thank you!

    • Reply


      January 21, 2016

      I've heard that quote before somewhere, and totally agree with it. Leaving is really hard... but having left is really easy. Good choices for Xmas and New Year, by the way -- having spent quite a bit of time in Tekapo and a few New Years in Sydney, I can recommend them both! :-)

Would you like to share your thoughts?

Leave a Reply