The reason there’s a lot of good advice for people in 20s/30s is that their problems are so easy, tons of people solve them well enough to produce generalizable value and share. They’re n>1 answers. 40+ you’re lucky if you can half-ass even your n=1 case. They’re n=0.5 answers.
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I'm sure we can find a 60+ Syrian refugee millionaire somewhere to satisfy both our tastes. More seriously, I agree people who have made it tend not to give good advice; you need to watch what they do on the way up, but they cover their tracks. That said, I am not sure talking...
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...to Unsinkable Molly Brown types is much more edifying. For example, I've spoken with Holocaust survivors, and been amazed at their resilience and spirit, but my main learning was, "wow, some people seem to have way more natural resilience and spirit than I ever will."
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