> The "should" in a statement like that is not a command. Or expected to be interpreted as a demand.
Personally, if the author's intention was what you suggest, I would argue this kind of writing is "lazy" for lack of a better word. Words have specific meanings, and they matter. The most simple (and I would argue proper) understanding of "your life’s goal should be to become the most improbable person you can be" is the plain text reading: the author is offering very specific advice which he follows with an argument for why it is good advice. In other words, he really means your life’s goal should be to become the most improbable person you can be as he stated.
> Being able to hold many viewpoints, without needing them to be right or wrong, or even consistent, is the beginning of efficiently acquired and scalable wisdom.
One can obviously consider multiple viewpoints and choose whether to embrace them or not. But in my opinion, wisdom comes from first-hand experience accumulated over a lifetime. It is not something that is "efficiently acquired", nor is it inherently "scalable."
Knowledge, on the other hand, can be efficiently acquired and scaled. But it is not always easily applied.
Being able to incorporate many incomplete and even contradictory models, without dissonance, is most certainly a scaling factor.
Wisdom often has unexpectedly wide application, and so is more multiplicative than it is simply additive.
Reality is never contradictory, but it is complex. The seeming contradictions in models are because models capture different subsets of reality, not because they are wrong.
Yes, we get wisdom from direct experience.
But also, many of us acquire even more from reading, conversing, observing. Life gives us one line of direct experience, but tens of thousands of insightful people sharing theirs.
Seeing the sense in other peoples viewpoints, adds value. Getting caught up in wording styles that other's don't have any trouble with, is not what I would call a skill. And seeing coercion, where someone put some effort into communicating and interesting idea, is not shedding light on anything.