75% probability that the following things will be gone by: LessWrong: 2020 Email: 2135 The web: 2095 Y Combinator: 2045 Google: 2069 Microsoft: 2135 USA: 2732 Britain: 4862
These don't seem unreasonable.
I'm not sure that this method works with something that doesn't exist coming into existence. Would we say that we expect a 75% chance that someone will solve the problems of the EmDrive by 2057? That we'll have seasteading by 2117?
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The author does not seem to understanding survivorship bias. He never approaches the question of whether the things he proposes are the reason for Musk's success actually work, or whether they happen to work for Musk in a context-dependent way. In other words, if you give this as advice to someone random, will they end up successful or an outcast. I'd guess the latter in most cases. This is in general the problem of evaluating the reasons behind success.
Also, unnecessary evolutionary psychology, done badly, even to the point of suggesting group selection. Ick.
The idea that using technical language (which isn't actually any more precise in meaning in the examples cited) in regular life is beneficial in being more scientific is also pretty suspect.