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I think the saying “money doesn’t bring happiness” is one of those unlearnable lessons - something you’ll never truly believe until you experience it firsthand.
I’m self-employed contractor and find my work quite meaningful, yet I still dream of living off passive income and never having to work again. But honestly, I’m almost certain my life would spiral out of control if that ever became reality. Work is what the rest of my life is built around - it’s why I get up in the morning. I’d like to think I’d find meaning elsewhere, and maybe that’s true, but I’m skeptical. I’m almost certainly just kidding myself when I think that I would. I'd just sit at home smoking weed and watching YouTube videos.
I don’t think work itself is the problem - it’s the soul-crushing drudgery people are forced to endure to survive, where there’s no sense of meaning or gratitude. Especially in jobs where you can’t even see the results of what you’ve done. If you’re sweeping streets, at least you’re outdoors, you talk to people, and at the end of the day you can see what you accomplished. But if you spend eight hours entering numbers into Excel in a toxic office environment, then of course it feels meaningless.
Enough money can remove the barriers to happiness.
If I suddenly had enough money to not need to work on order to survive, I would still "work," except it would be on my own terms, not someone else's. There are loads of things I want to do and not enough time to do them. I dream of being able to prioritize my own time for myself rather than needing to sell a third of my life to a megacorp for bread.
"All I ask is the chance to prove that money can't make me happy." - Spike Milligan
But if that's what you enjoyed then that is what you'd do and it would make you happy. If it didn't make you happy you wouldn't do it. So maybe that's how your life after work would start, but if you became restless and stopped enjoying it you have your background in contracting and you'd probably take on some more enjoyable creative aspect of that role.
In the end your life doesn't only have meaning if it's defined by a job title, it's defined by how you live it. It doesn't even need to have "meaning" outside of your own enjoyment of life.
I disagree. It might be enjoyable in the moment, but looking back, it wouldn’t be something I’m glad I did. Happiness is a fleeting emotion - what most people actually want is a deeper sense of contentment. And I don’t think chasing hedonistic pleasures gives us that.
I don’t look back fondly on the countless hours I’ve wasted staring at screens, but I do cherish the memories of doing difficult, effortful things - even the ones that weren’t all that enjoyable in the moment - because they left me feeling satisfied and proud afterward.
That's not really how people work though. There's a ton of other motivations than happiness.
Shit man, I don't even know what would make me happy.