I do agree with the idea that losing money can teach you more than making it — though with some caveats. Success reinforces what you’re doing well; losses force you to confront mistakes, assumptions, risk, and your emotional reactions in a way that wins often don’t. However, losses are only valuable if you reflect, adapt, and don’t repeat them.
The lesson I have learnt along the way comes from a story I read. A memoir style book read and recommended by close friends.
The Story in Brief
Jim Paul was a successful trader on Wall Street. He made a lot of money but eventually lost most of it. The losses came from a combination of overconfidence, letting losses run rather than cutting them early, misjudging risk, and not having strong discipline or rules to stop bad decisions. He made it clear that many of his mistakes were psychological: stubbornness, faith that markets must rebound, ignoring warning signs, believing that because something worked before it would always work.
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