I tried using Goodreads' recommendation engine with a shelf of the below books, but the results weren't satisfactory (quite incongruous, really).
Ishmael by Daniel Quinn
A Naked Singularity by Sergio De La Pava
Zen and the Art of Motorcycle Maintenance by Robert M. Pirsig
Lila by Robert M. Pirsig
The Elegance of the Hedgehog by Muriel Barbery
Foucault's Pendulum by Umberto Eco
Any recommendations based on books in this vein are much appreciated!