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Trent, these columns are hurting my neck! I cannot stop nodding in agreement and shared experience, thank you! Particularly resonating this time "household responsibilities become my day" YES. And your 'ought to' list - I am plagued by guilt that mine isn't very big and that I'm without purpose because I'm not getting to any of the things on it! Thanks again for your honesty.

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Hey Bro, long time no see but I really appreciate your raw honesty here. I think by getting into this situation you're forced to face some tough questions about meaning which the rest of us can put off until much later. I don't know you that well, but still some things about your character are blindingly obvious. You are capable of doing big things, and you are inspiring to be around. There aren't that many people like that. When you joined Trade Me as head of product, I remember the enormous feeling of optimism and excitement you brought about the future. Whatever you choose to do, keep in mind that having vision, tackling hard problems and building a team is a gift. It's good to understand your own wants, but character is found through actions, or how you react to hardship. I have recently taken to the stoics and you might like this quote from Mr. Aurelius, the Roman emperor: "And a commitment to justice in your own acts. Which means: thought and action resulting in the common good. What you were born to do.”

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Hey man, I love the stoics. I only recently realized how much they aligned with my world view.

So I read this article because since work from home was thrust upon me during the pandemic, I feel sort of retired. Not as busy, I gained back 3 hours a day from commuting. And I don’t see or interact with many people. It sucks.

Find myself going through everything touched upon in this article. Ugh, yup!

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Hi Curtis, I'm glad the article resonated. So far I haven't gone much into solutions for all this stuff, but I have a bunch more stories to tell on how I've moved on. Stay tuned!

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Hi! Lester! I think you are right - some of these questions don't show up until you take a step back from work life. Of course, sometimes that step back is forced - in writing this I've heard from people who have struggled to find work, or who have spent years looking after sick parents, and they are wrestling with some of the same things.

Thanks for your kind comments about my time at Trade Me. One of the great things about being the first person to take a role is that you can kinda write your own job description. But the bad thing is that you are also subject to lots of different interpretations as to what should be in that JD. I remember being daunted when I asked people around the business what they thought a CPO did and what my priorities ought to be 😬.

It seems like the stoics are making a come back. I should read them some more - chances are very high that they wrote about all this stuff I'm talking about a long time ago.

Go well, stay interested and interesting

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Guilt! I’m not retired yet but certainly work less and have enough free space to fill that I often find myself feeling a form of guilt. I frame it more as not having permission to do the things I enjoy indulging in. The irrationality of giving yourself permission to do something you clearly want to do is maddening!

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Is there a pattern that you've found? Are certain types of non-work activities more guilt-inducing than others?

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I wonder if there is a free time dynamic where free time is only valued/enjoyed if it is earned with a corresponding ratio of ‘opposite of free time’. We all think free time sounds perfect while we’re in full time jobs & parents and in the middle of it, but when it happens the value of it only lasts so long until all the things you describe above manifest themselves (Problem creep, guilt of non achievement etc).

I wonder what that ratio is? Am thinking that its lots of 'non free time' to low amounts of 'enjoyable free time'.

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Hi Matt! What you re talking about makes perfect sense to me. If every day was a holiday, I think that would get old. It's the contrast which makes it fun. Up to this point, I've mostly been whining, but pretty soon I get into recommendations, one of which is to keep working in your retirement 😝

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