Interesting question, and a quite difficult one for me to answer as I'm refactoring much of my thinking presently. I'll offer a list, some authors, and some guidelines, largely based on books which radically changed my thinking.

Madelaine l'Engle's A Wrinkle in Time. A quite profound children's book with lifelong impacts.

https://www.worldcat.org/title/wrinkle-in-time/oclc/22421788

Frank Herbert's Dune introduced true complexity into storytelling for me.

https://www.worldcat.org/title/dune-frank-herbert/oclc/52908...

James Burke's books Connections and The Day the Universe Changed, and their accompanying television series, were a profound introduction to the history of technology, science, ideas, and philosophy. Though 30+ years old, they remain highly current and relevant.

https://www.worldcat.org/title/connections/oclc/4494136

https://www.worldcat.org/title/day-the-universe-changed/oclc...

Jeremy Campbell's Grammatical Man (1984) introduced the concepts of information theory and their deep, deep, deep interconnections to a tremendous number of interconnected systems, many not explored within his book. Darwin's The Origin of Species, James Gleick's Chaos, and many of the works of Santa Fe Institute members, including John C. Holland, J. Doyne Farmer, Geoffrey West, W. Brian Arthur, David Krakauer, and Sander van der Leeuw, continue these themes.

https://www.worldcat.org/title/grammatical-man-information-e...

https://www.worldcat.org/title/chaos-making-a-new-science/oc...

William Ophuls' Ecology and the Politics of Scarcity (1977) is perhaps the best, most comprehensive, shortest, and most readable exposition of the fact, reality, dynamics, and interactions of limits on the present phase of fossil-fuel fed economic growth I've found. This is a book I recommend not only for the message, but the author's clarity of thought and exposition, his meticulous research, exquisite bibliographical notes, and, given the nearly 30 years elapsed, testability numerous of his predictions, some failed, yes, others uncannily accurate. Rather more the latter. In a similar vein, William R. Catton's Overshoot looks at the ecological dynamics in more depth, with much wisdom, the writings of Richard Heinberg cover the ground of limits fairly accessibly and more recently. Vaclav Smil in numerous books addresses technical factors of the profound nature of the past 250 years, and implications for the future. Meadows, et al, in Limits to Growth set off much of the post-1970 discussion (though they're hardly the first to raise the question -- it dates to Seneca the Elder),

https://www.worldcat.org/title/ecology-and-the-politics-of-s...

https://www.worldcat.org/title/overshoot-the-ecological-basi...

https://www.worldcat.org/search?q=au%3Aheinberg%2C+richard&q...

https://www.worldcat.org/search?q=au%3Asmil%2C+vaclav&qt=res...

Though hardly pessimistic, Daniel Yergin's book The Prize (and TV series) impressed upon me more than any other just how much petroleum specifically changed and transformed the modern world. Though intended largely as laudetory and championing the oil industry by the author, my read of it was exceptionally cautionary. The impacts on business, everyday life, politics, wars, industry, and transport, and the rate at which they occurred, are simply staggering. You can continue this exploration in Vaclav Smil's Energy in World History (1994) (I've recommended Smil independently elsewhere), and a rare but profound two-volume set I'm currently reading, Manfred Weissenbacher's Sources of Power: How energy forges human history (2009). The shear physicality of this book speaks to the message -- it's divided into five parts: 1) Foraging Age (6 pages), 2) Agricultural Age (156 pp), 3) Coal Age (160 pp), 4) Oil Age (296 pp), and 5) Beyond the Oil Age (142 pp). That is, the ~2 million years of pre-agricultural existence are little more than a footnote, the 8,000 years of agriculture roughly equal to the 150 years of coal, and the 100 years of petroleum use roughly twice either. The oil and post-oil ages comprise their own volume. Yergin followed up with The Quest, continuing the search for oil, though I've been less impressed by it.

https://www.worldcat.org/title/prize-the-epic-quest-for-oil-...

https://www.worldcat.org/title/energy-in-world-history/oclc/...

https://www.worldcat.org/title/before-oil-the-ages-of-foragi...

https://www.worldcat.org/title/oil-age-and-beyond/oclc/83762...

Adam Smith's An Inquiry into the Nature and Causes of the Wealth of Nations is among the most-cited (and most incorrectly cited), least-read books of high influence I'm aware of, outside religious texts (and perhaps it is a religious text to some…). The author's message has been exceptionally shaped and manipulated by a powerful set of forces, quite often utterly misrepresenting Smith's original intent. Reading him in his own words, yourself, is strongly recommended. I'd also recommend scholarship particularly by Emma Rothschild and Gavin Kennedy, though also others, on Smith. Contrast with the portrayal by the propaganda disinformation front of the Mont Pelerin Society / Atlas Network / so-called Foundation for Economic Education, and much of the modern American Libertarian movement (von Mises, Hayek, Friedman, Hazlett, Rothbard, and more recently, Norberg). Contrast The Invisible Hand (1964), a compilation of essays published by Libertarian house Regnery Press in 1966, at the beginning of the rise in public use of Smith's metaphor to indictate mechanism rather than an expression of the unknown.

There are numerous editions of Smith, I believe the Glasgow is frequently cited by Smith scholars: https://www.worldcat.org/title/glasgow-edition-of-the-works-...

https://www.worldcat.org/title/economic-sentiments-adam-smit...

https://www.worldcat.org/title/adam-smith-and-the-invisible-...

https://www.worldcat.org/title/adam-smiths-lost-legacy/oclc/...

https://www.worldcat.org/title/invisible-hand-a-collection-o...

I'd like to put in recommendations on technology specifically, but am still searching for a good general text. The material's covered somewhat in the chaos and complexity recommendations above (Campbell et al), though I'd add Joseph Tainter's The Collapse of Complex Societies. Charle's Perrow has several excellent books including Normal Accidents and Organizing America. I'd like to reference something concerning Unix, Linux, and programming, perhaps Kernighan and Pike's The Unix Programming Environment, Linus Torvalds' Just for Fun, Richard Stallman's The GNU Manifesto, and Steve McConnel's Code Complete. The O'Reilly book Unix Power Tools also encapsulates much the strength of the Unix toolset. All these are somewhat dated.

https://www.worldcat.org/title/collapse-of-complex-societies...

https://www.worldcat.org/title/normal-accidents-living-with-...

https://www.worldcat.org/title/organizing-america-wealth-pow...

https://www.worldcat.org/title/unix-programming-environment/...

https://www.worldcat.org/title/unix-power-tools/oclc/5238168...

https://www.worldcat.org/title/free-software-free-society-se...

https://www.worldcat.org/title/just-for-fun-the-story-of-an-...

https://www.worldcat.org/title/code-complete-a-practical-han...