There's something funny about making a list like this. To force organization and legibility on the non-rational seems futile.
Yet, when you have no idea where to begin, it's helpful to have a jumping off point.
So, this is my version of a recovering rationalist starterpack.
1 - Impro - Keith Johnstone
Impro is a collection of essays on improvisational theatre, but it's lessons apply even if you've never stepped on stage.
Johnstone wants his students to see the world in a spontaneous, playful way. He guides them to this perspective with a variety of exercises: status games, shouting the wrong name for objects, wearing masks.
A fascinating read, give Impro a shot.
2 - Making Comics - Lynda Barry
Impro's an amazing book, but you probably don't have access to an Improv class, or even if you do, you probably don't have Keith Johnstone to guide you.
Making Comics isn't a typical drawing book. Instead of practicing perspective lines and perfect ovals, you're asked to squiggle, to make silly connections, to move freely and observe what shows up.
The ideas in Impro didn't totally click for me until I tried some of the exercises from Making Comics. Barry has a way with drawing that makes it easy to tap into your unconscious.
Plus the art style is just incredible.
3 - Seeing Like a State - James C. Scott
We all have a deep-seated desire for certainty, a need to make things legible and understandable. This desire makes draws many to rationalist thinking, and indeed rationalism can make many fields more legible.
Seeing Like a State demonstrates how this desire for legibility can lead to catastrophic failure in public policy, citing examples ranging from Germany's scientific forestry to China's Great Leap Forward.
The main idea holds for individuals too: seeking legibility while ignoring the illegible can cause us to make grave mistakes.
Consider starting with Venkatesh Rao's notes on "Seeing Like a State" if you're short on time.
4 - Ways of Attending - Iain McGilchrist
Ways of Attending is a short paper summarizing McGilchrist's much longer "The Master and His Emissary".
McGilchrist discusses the left and right hemispheres of the brain, but rather than focusing on what each side does, he focuses on HOW each side does. Both sides of the brain are involved in basically all of our activities, but the way they pay attention to the world differs greatly: the left in parts, the right as a whole. The left erroneously thinks it can go without the right, producing rationalists like you and me.
Read Ways of Attending (If Amazon pricing is expensive, try to find a cheaper copy elsewhere...)
5 - Finite and Infinite Games - James Carse
“There are at least two kinds of games, one could be called finite; the other infinite. A finite game is played for the purpose of winning, an infinite game for the purpose of continuing the play.”
Carse builds on this straightforward idea of infinite games, leading us through ever-deepening ideas about culture, religion, and ourselves.
This book radically shifted the way I think about living. A must read.
Don't read books just because they're on a list. Read books that catch your attention.