I noticed a point of intersection between the books The Black Swan and How to Fail at Almost Everything. These two authors share some similarity in their epistemological position. Namely, we learn by doing. We want to give ourselves opportunities to get lucky.
Specifically, How to Fail advocates for thinking in terms of systems - the things we do need not add up to a concrete something. Rather, we try new ventures - startups, patents, ideas, books, practices, routines - with only the desire to become a better person. While the 'goal' tells us to get a job, the 'system' tells us to become the person who can better get a job. By exposing ourselves to reality and getting feedback, we learn what the world likes and doesn't like. This lets us encounter positive Black Swan events: low probability events with an outsized impact that are not within the confines of what we previously knew.
For instance, if we were to consistently network and reach out to people for chats in exchange for sharing knowledge, we expose ourselves to the low probability event of getting a nice job recommendation. If we don't, perhaps we get some juicy gossip, or minimally a pleasant conversation. If we were a serial entrepreneur, one of those business ventures will strike gold.
If it is true that timing and luck matters so much (think of Gladwell's What the Dog Saw and The Tipping Point), we should let ourselves roll the dice as many times as we possibly can. This is perhaps the 'intellectual' polish on the notion that "luck finds those who are prepared". This "preparation" is not in the sense of "having studied for an exam", but rather "preparation" as having multiple systems that expose yourself to large positive outcomes.
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