You know, I have this exact feeling about the idea of "the meek shall inherit the earth" philosophy expounded in the Sermon on the Mount, but I haven't until now thought of it in terms of stoicism or buddhism. It's definitely important to have some idea of the difference between "fair" inequality that's just the luck of the draw that's unavoidable to some extent, and the "unfair" inequality that's a result of oppression and exploitation. It's almost certainly a bad idea to seek to simply stop comparing anything and be oblivious to all the differences between people. But like a lot of our natural thought processes there's a healthy version and a pathological version, but it's never really clear where exactly one becomes the other. There is a bit of a built in failsafe in Buddhism that is the idea of the "middle way", that indicates any "extreme" position is liable to be unhelpful. I find myself using that a lot, as I tend towards extreme views and am prone to oversimplified, black-and-white thought.
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