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I often contemplated about people like Zuckerberg who had massive success with the first thing they built and then have to come to terms that not everything they touch turns to gold. I wonder what kind of feeling that must be if your greatest success happened in your 20th. How do you measure your successes then?

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This dynamic has been explored extensively in the creative fields. Most namely with the music industry and the "sophomore album curse".

Interesting. Never heard that term. Will check it out thanks.

My cynical answer: I think they reframe their history to see it as a series of ever-larger successes -- with some setbacks maybe. They avoid introspection that might lead to the unpleasant conclusion that they have actually gone off the rails and caused societal harm since their initial success. By and large their net worth has continued to increase, and that's the measure that they're comfortable with associating with success, and they see that as validation. Plus, they are surrounded by people who have the same incentives to lie to themselves and to each other.

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