Sometimes, Breaking Up With Your Boss Is Hard To Do

On Friday I’m going to have that “it’s not you, it’s me” chat with my boss.

I’ve had sleepless nights over it. I don’t know how he’s going to react. I’m not sure what I’m going to say. Do I go into all the trivial things that really piss me off, or do I talk about the bigger picture — the “I hate working full-time” picture? The “Singaporean manners shit me to tears” picture? The “we are very lonely here” picture? Do I break it to him gently, or just hit him with the fact that I’m quitting?

My boss is quite dishy. He is calm, considerate and patient when appropriate; sarcastic, snarky and inappropriate when appropriate. I’m going to miss him. I don’t really know if I can convey how much I will miss him without sounding like a lunatic stalker. (He’d probably love to have a stalker, too, and I just can’t give him the satisfaction.)

I’ve done this before, broken up with bosses. Some breakups came waaaaay too late. One boss left me. That hurt, a sharp and personal pain like an unexpected bikini wax.

One boss I mourned for nearly a year. Before the breakup, we were on the phone together several times a day. He’d fly to Melbourne for drinks and fancy dinners. He’d fly me to Sydney and put me up in a five star hotel and let me loose on the posh parts of the city with a company credit card. He even danced a jig when I snagged an interview with someone-or-other — I forget now. But I missed him after we broke up. And I missed the company credit card, too. Oh yeah, that boss was dishy too.

Another boss, an asthmatic, would put a grin on my face every morning when he called to breathlessly ask me what I was doing that day. If it was anything vaguely exciting, I’d hear the psssht of his inhaler and feel the thrill of victory.

I’m going to miss my boss. I’m going to miss the camaraderie of working in an office, even though the camaraderie is severely curtailed by the need for each of us to stare at our computer screens in slave-like-drone-like-zombie-like-devotion for 7 hours and 50 minutes every day. (The company turns a blind eye to the 10 minutes a day we spend peeing and refilling our water bottles at the water cooler.)

I lay awake at night and worry that I’m making a big mistake — letting go of the stable income, the nice house in a friendly leafy street, the company health insurance, the company retirement plan. I try to remind myself how miserable I am at the prospect of catching the bus every day, getting into the lift in my office building, facing the crowds at lunchtime, then catching the bus home again. The work is not so interesting but it’s do-ableΒ  Getting to work kills me. Every trip to the ladies is another voodoo pin in my soul. Oh, and paying the rent, which chews up more than 40% of my salary, is making my badly-dyed orange hair go grey.

So… deep breaths… I have to have the chat. I’m going to have to say, out loud, “time for a chat”, and then walk the walk of shame past so many cubicles into one of the glass-walled conference rooms. Then I will tell my blue-eyed, dashingly grey-haired boss that we are leaving Singapore and, therefore, quitting. It will be the end of the relationship. There is no way I will have his odd British respect once I’m not helping him look good to his bosses. He won’t see it that way, of course. But that’s the stark reality of our relationship. All’s well when the underlings make the boss look good.

Sometimes, breaking up is hard to do. And it really is not him, it’s Singapore. It’s Singapore public transport, it’s working full-time, it’s the night-owl baby, it’s being mistaken for a grandmother, it’s the fact that I’m not learning anything in this job, it’s the fact that we have made no new friends in Singapore in 15 months (we have made colleague-friends and renewed wonderful old friendships, but it’s just not enough, it’s not a fulfilling life), it’s being hot and sweaty all the time, it’s putting on weight from the oily local food, it’s the lack of exercise opportunities in my sleep-deprived working mother life, it’s the shift work, it’s the fact we’re not saving, it’s the fact that this is not an enjoyable life we have in Singapore.

It’s really not him. It’s me. It’s my need for a happy family living an exciting enjoyable fun life. It’s totally me. Poor bloke. He never really stood a chance, did he?

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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. Woooow, good luck. Loved this post – despite the nervous times for you. It sounds as though you’ve been over and over about the pros and cons and there’ll be something else out there for you. Have you got plans? (Sorry if you’ve written about your plans already, I’ve been a bit off radar this summer – just super busy with visitors.)
    We’re rooting for you all anyway. πŸ™‚
    Turkey’s For Life recently posted..Turkish Recipes: Spicy Chickpea and Aubergine Stew

  2. YOU CAN DO IT! i am so excited for this next chapter in your life. brava!! good luck on friday…
    wandering educators recently posted..Dog Meets World Foto of the Week: a New Smile in Guatemala

  3. CONGRATULATIONS! Trust me, I know what you’re dealing with in terms of sleepless nights. Almost 4 years ago now I was siting with my wife with our baby–just a month old–in the next room. I was preparing to have “the talk” with my boss the next day.

    I said something to my wife like, “I don’t know.. should I not go through with it???…”

    She asked me what I was thinking.

    I said, “What if we can’t make the money?”

    She said, “If it’s the money, quit.”

    I can tell you that this life–family travel lifestyle–is not easy. You give up the perks. The corporate credit card. The health plan. A paycheck every two weeks.


    You’re not crazy. I promise you that you’ll look back on your decision as the best of your life.

    When things are tough– we often say in sort of depressed tone “this is the life we chose.”

    We say it sarcastically knowing the storm will pass because the next day when we’re sitting on beach somewhere (our bank accounts still empty but who cares) we say to one another in a much happier tone “this is the life we chose.”

    Look forward to following your adventures!!!

    • The Dropout says:

      Great to hear that it all worked out for you. We, too, are a bit worried about where the money is going to come from. But it just doesn’t make sense to spend so much time and effort just to pay the rent in a city we aren’t enjoying. Not that Singpaore is horrible, it’s just not for us.

  4. Congratulations! Everything happens for a reason, you’ve been compelled to it for a bigger purpose, it will free you and open up doors you never dreamed possible!

    Good for you!

    Nancy & Shawn

    p.s. we have quit our jobs too we know the feeling… makes us want to say, “fly birdie fly!” πŸ™‚

  5. Erin says:

    I’m book marking this post so that when it’s time for me to quit, I can just email this to my boss πŸ˜‰
    Erin recently posted..You May Be Wondering…

  6. adventureswithben says:

    Best of luck!

  7. Congrats on making the big decision. I hate resigning to bosses as well. That may be because I have always had wonderful bosses, but I think it is also because I hate to disappoint people. But in the end, it is about you living a fulfilling life.
    Stephanie – The Travel Chica recently posted..Gallery Nights in Buenos Aires

  8. I’m so excited for you! This is start of many wonderful adventures. Good luck – just take a deep breath and do it!
    Nancy from Family on Bikes recently posted..What to do with an old brown bathtub – *CONTEST*

  9. Andrea says:

    Congrats! Life’s too short to be unhappy
    Andrea recently posted..Tasting Vienna at the Outdoor Film Festival

  10. I did this back in March. Working just didn’t make sense anymore. I had stopped learning new things long ago. My career was not moving forward. My family was suffering. Most of my paycheck went to a crappy daycare. It was time for a change. I loved my co-workers though. With only 8 of us, we had become a little family over the years. I had an amazing boss. It was the hardest job to leave. They have all been hard, but this was worse. I finally had a boss who was my friend and had tried to help me navigate the waters of new motherhood, but in the end it just wasn’t working. It was a hard talk, but it was SO worth it. I am now able to focus on my son. I can focus on where I want my career to go (still figuring that out) and find some happiness in life. Cause really, we don’t have that much time to live in misery. Might as well make the most of what time we do have.
    You will do great! Deep breath and go for it. Amazing things are down the road. I can’t wait to hear all about them.
    walkingon travels recently posted..That Dam Ice Cream Shop

    • The Dropout says:

      So happy to hear from someone who’s further down the path than me.
      Here’s to great things for both of us!
      I love your comment “might as well make the most of what time we do have”. That thought has been a big motivator for me at various points in my life.

  11. Amy says:

    Love this post! You are such a good writer πŸ™‚ I am so excited for you and can’ t wait to hear about the break up story. Good luck!
    Amy recently posted..Feels Like Home

  12. Sailor says:

    I am not sure when I am going to break up with my current Boss. I hope it happens very soon πŸ˜€
    Sailor recently posted..Touring the Galapagos Islands – A Dream Cruise

  13. Mark Wiens says:

    Excellent piece of writing and it’s so incredible that you’ve chosen to make the giant leap to pursue a better life.

    Keep it up and I’m excited to see things in the future!
    Mark Wiens recently posted..Egyptian Budget Travel Guide: Cost of Traveling to Egypt

  14. Great article. I remember breaking up with my boss a few years ago. Never a fun moment. Good luck!

  15. Mica says:

    Much congratulations on your move. I just arrived to Singapore this morning and it depressed me. Well, that might be because I came from Bali where the sun shone every day and the cool ocean breeze was dreamy, but this big city, with its unsmiling people and cloudy/rainy weather is really bringing me down. I can’t imagine living here at all. Good on you for taking the plunge. I’m headed to Chiang Mai in 5 days. And really, if you’re not happy, then what’s it all about? See you when you get to Chiang Mai!

    • The Dropout says:

      It’s not always cloudy and raining here in Singapore, Mica. It’s usually sunny and sticky!
      Singapore people aren’t big smilers. But if you stop and ask anyone for help, they will be amazingly gracious. I don’t know why everyone walks around with such dragon faces. It really doesn’t reflect how most people are. We are very lucky in that our baby usually makes people smile and sometimes even chat about baby things.

  16. […] ninny. But instead, I just get his sweetheart side. Today of all days, when I’m planning the “it’s not you it’s me” talk with […]

  17. There are little things we all learn to put up with in life, because the truth is that no place or situation is perfect. Some ‘settle’ for a blah job because it pays decently and allows them to live in a great place. Others ‘settle’ for a smaller place to live so they can choose to stay at home with their children and not work, etc.

    But life truly is too short to settle for a mindnumbing job that doesn’t pay sufficiently for the cost of living in a city that you don’t enjoy. You KNOW deep down that there is work out there that calls to you, would get you excited to get up in the morning to rush to do it, would allow you to spend more time with your family and is in a better place where you’ll enjoy the TOTAL quality of your life.

    So rock on, get it done, break up with Mr. Dishy, and then go home and celebrate. Then sit down and write about how it went and what’s to come, we all want to know the details! recently posted..Tallinn, Estonia: Further North

  18. Sherry says:

    I never forgot my favorite boss, too. Its hard to find someone similar and I may never even find him again. But the hardest choices in life sometimes rewards us with betters things. Not many people can take the step to change. I applaud you for your courage to take control of the life you want. I’m sure what lies ahead can only be better for you.

  19. Great post!! Love the angle you took. Good luck and I’m sure it will all go perfectly.

  20. Grace says:

    Oh my big plans! Very excited to find more about it. Good luck! There’s one more boss break up story you will have to tell us about. =)

  21. Having just had a similar chat with my former boss a couple of months ago, I feel your pain. But if you’re not happy, you’re not happy. And that my good friend, is that. You are doing the right thing!

    And I absolutely LOVED the writing here! Good luck, godspeed, and get out while you can! πŸ™‚
    Raymond @ Man On The Lam recently posted..Travel Photo of the Week — Lahu Hill Tribe Women, Mae Hong Son, Thailand

  22. Sophie says:

    What a fun, yet poignant post! Hard to say goodbye, even to good bosses (don’t think there are that many of them), but life comes first! Good luck!

  23. I enjoyed this. I just quit a job where I had the opposite problem – I HATED my boss! πŸ™‚
    Chris @CAroundTheWorld recently posted..Alaska’s Inside Passage: Tracy Arm & Sawyer Glacier

  24. Congrats, it seems as though exciting things are coming your way πŸ™‚
    Nomadic Samuel recently posted..Singapore Photo Essay | FOGG Odyssey

  25. Deb says:

    What a beautifully written post. Good luck on your new chapter in life and congratulations for having the courage to follow your heart and live your dreams.

  26. Nancy says:

    Glad you’re going for it; I have never regretted what I’ve left behind; in fact, always wondered why I took sooooo long to do what I knew all along that I wanted to do.

    Good luck to you–stay happy.
    Nancy recently posted..Ma’am, Step Away from the Trowel

  27. chenyze says:

    gee, i really came upon your blog a little too late! read it recently, only because Robyn Eckhardt reshared your interview with her and i was thrilled when I found out that the author was living in Singapore. Wish I could have made Singapore a little more pleasant for you!

  28. Rahul says:

    Congratulations for taking a courageous call… I guess now you must be living an exciting life…. Ironically, conformists still say “quitting is for losers”….
    Rahul recently posted..Agra Diaries: Taj Mahal in Moon light

  29. I’m facing the same problem right now. For the first time in my life, I have a great boss, but I would also like to quit my job, be completely free and travel for at least a year… Thanks for sharing you experiences, it gives me courage πŸ™‚
    Annie@GreenTravelReviews recently posted..Captain’s Desert Camp- Wadi Rum, Jordan

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