Cedric Villani's Birth of a Theorem (Theoreme Vivante) is about what it means to do hard intellectual work. If you do not care about mathematics, but care about intellectual work, do take a look. There's lots of technical detail, but what is striking is the process of doing the work, the insights that cause him to rewrite it all, hangups that eventually are dealt with, working with a collaborator,...
John Nagl's Knife Fights is about war and counterinsurgency. I find his chapter 8, an overview, to be thoughtful, balanced, fair, and interesting: about the role of the US, about what kinds of wars and military encounters are likely, and about the political world. Nonpartisan, not ideological, a nice read. He was a Lt. Col in the Army, with lots of experience.
I find that descriptions of the world, whether they be of intellectual endeavors or of practical ones are best provided by actual practitioners who are both reflective and open to alternative positions. Theoretical and outsider perspectives are sometimes helpful, but often they need a healthy dose of actual frustrations and practices if they are not to be unhelpful.
The only way my own descriptions are justified is that I try them out on actual practitioners, and ask, Does this sound right? Often, the response is, So what?, in the sense that what I am saying is obvious to the practitioner. But, in general, it is not so obvious to others. It helps that I bring a wide range of models to the table, looking for analogies and perspectives: BUT, I could just be wrong, unless my work is tempered by experience (my own, or others). It's easy to teach mature practitioners, since if what I say makes sense to them, they get it. Nothing I say is "too theoretical," since if it makes sense they see it in actual terms. Teaching inexperienced students is much harder.