I've been in a book club with college friends for the last few months, and our reading list has ended up being interesting and powerful. Maybe even useful! The through-line has been 'life and societal systems from the perspectives of games', and 'designing a life well-lived through communities of play'. YMMV.
Finite and Infinite Games, James Carse
The Well-Played Game, Bernie DeKoven
“Bryn Mawr Commencement Address (1986)”, Ursula K. Le Guin
The Gardens of Democracy, Eric Liu and Nick Hanauer
“Judgement of the Birds” and “The Star Thrower” from The Star Thrower, Loren Eiseley
Mary Oliver, Upstream (all of Section 1, and then “Emerson: An Introduction” and “Some Thoughts on Whitman” from Section 3.)
… and a host of related articles and personal reading. Personally, I've read at least parts of a few very related books in the same period:
A Pattern Language, Alexander, Ishikawa, Silverstein, Jacobson, Fiksdahl-King, Angel
The Infinite Playground, Bernie DeKoven with Holly Gramazio
The Immense Journey, Loren Eiseley
Politics is for Power, Eitan Hersh