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You can practice the mindset by writing a toy solution for the problem, then listing the reasons why you consider your solution just a toy. This develops a fundamental skill of engineering, which isn't understanding whether a system will fail (it will always eventually fail, even if the first reason is that the sun explodes), but rather when and how it will fail. You can make a whole career out of pulling on that thread.

(I worked at Google with Bob in the mid-2000s. I might have interacted with him once or twice on the internal Java and Guice mailing lists, but never met him in person. He was supremely helpful and knowledgeable, and I admired him from a distance.)



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