Five fuzzy suggestions, when there's no single book condensing the best truths on a topic:

1. Read a lot.  In computer systems, go back at least as far as the 1960s.  Be skeptical of what you read and hear, but file it away in your brain.

2. Be especially skeptical of ideas targeted at dotcom brogrammer branded certification cottage industry cultists.  There is a lot of enthusiasm, and some good ideas (some of the best ideas are actually coming from elsewhere), but also make-believe, circle-self-flattering, dotcom MBA/VC orientation, and pundit opportunism.

3. Be skeptical even of the Racket community.  I think we are one of the all-around best communities, and are well-intentioned, and thoughtful, and reasonably humble.  But we still have strengths and weaknesses, I think we're a bit more incestuous or parochial than I suspect is optimal, we don't know everything that anyone else knows, we don't know things that no one yet knows.

4. At the same time you're being skeptical of everything, be humble and open to ideas.  I think smart people are always trying to maintain a balance in this regard, since I suspect we all have biases that suggest the need for conscious balancing.  I wonder whether it's human nature that we each will always be too skeptical of some things, and too trusting of other things.  (Personally, some of my biases have me loving a vague derisive sense of the term "brogrammer", though that's bad of me, and I should try to remember not to summarily reject any ideas from that direction, and I should not be dismissive of people who initially appear to fit an imagined stereotype of bad practices.)

5. Design and build lots of things, experiment a lot, think constantly about the big and the small, and second-guess as much as you can without being paralyzed into inaction.

This is an ongoing process of self-discipline -- not, I think, something we can ever say we've achieved, like we've reached a certain level, and then rest on our laurels.  (Personally, I'm always making mistakes relative to things I thought I already knew, and, at this rate, will never ascend to some higher echelon of wisdom, but I think the attempt at discipline is good.)

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