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Re:Ask HN: Mind bending books to read and never be the same ... by skilesare on Tuesday May 12, 2020 @08:42AM (#23153298)
All the things by Christopher Alexander(Start with timeless way...explore the pattern language...move on to Nature of order...then others.)

Zen and Lila by Pirsig

Beginning of Infinity by Deutsch.

Re:Ask HN: Mind bending books to read and never be the same ... by talkingtab on Tuesday May 12, 2020 @10:30AM (#23154363)
I second Christopher Alexander of "Patterns" fame, but his "Notes on the Synthesis of Form" tops my list and is available as a pdf.
Re:Ask HN: Mind bending books to read and never be the same ... by carapace on Tuesday May 12, 2020 @12:05PM (#23155579)
Nature of Order is (IMO) probably one of the most important books of the twenty-first century.