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> So, how does one unlearn "poverty mentality"?

Take a few risks. Start with risks that aren't real, like going to a restaurant that no one you know has ever heard of.

Once you have the experience that nothing bad happens, or if it does, it at most wasted a little money and time, work your way up to more rewarding risks.

Don't go as far as the Into the Wild guy though: he never realised how much "nothing bad" happening was due to other people bailing him out until he took risks someplace where that wasn't going to happen.

It's like writing a program: do it in small chunks and check each bit of functionality before committing.

No hacker ever stopped writing a program because they encountered bugs now and then.

Does this make sense?