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One of the problems with our little discussion here is that you equate success to money and I equate success to life. In my world, the millionaire can be the loser for leading a financially abundant but otherwise unfulfilled life, while the bum may be the winner, happy to be exactly who and where he is.
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well it's not me, but society that equates success with money. If you ask me, the deeper problem is to equate success with something externally visible in somebody's life. It's sort of a catch-22 though, as if something isn't visible, you can't see it, and can't make an accurate judgment of their character. I'm not against judgment at all, I think it's something we should do, but we need to be careful about it.
I don't think anybody seriously believes money can buy fulfillment but it can get you the opportunity to achieve such. Yes some resourceful souls can lead incredibly fulfilling lives in poverty, but they might be able to make more of an impact if they have some of the social capital money gives you. Take this website for example, would Steve Pavlina be getting so much traffic if he wasn't making lots of money with his website? Maybe but he'd have to be up to something else. Making money is part of his deal.
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For the record, the people who I would call losers would be the kind of folk who live off social security, while being perfectly capable of doing some work or volunteering and then spend their lives complaining about how all the foreigners drive a nicer car then they do. It is a paring of the least amount of problems with the loudest complaints. A complete and utter lack of any sense of one's responsibility in life.
(Fortunately, these people are but a minority)
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Well I doubt such people are very happy with their existence. They simply aren't good at discerning such and taking appropriate action. Instead of writing them off as "losers", maybe send a silent prayer that they figure out what they are doing wrong and change. Maybe it'd be pointless, but as humans with human circumstances I think even the most vile parasite deserves some benefit of the doubt (I include the worst of the worst aka the Hitlers and child murders of the world and no I don't think we should give any legal breaks to such people). At least until technology gets good enough where we can determine who is a fellow human and who is a blood sucking android... ;p