The world is a weird place. I think most things have risks but sometimes, it's high risk and high return. It's a gamble on how things work but I do think that overconfidence is a bad thing. If something failed, you need to figure out what went wrong to stop making the same mistake. I think being careful is never a bad thing and doing things steadily isn't a bad thing at all.
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Yes, I agree, it's important to make assessments and check where it all went wrong, else we're bound to always repeat the same mistakes we've made in the past.
Confidence has never been something I have in excess. This is why I'm rather careful and unwilling to sacrifice my position.