Non-exhaustive repository of content that I've found enlightening.

A tutorial on reinforcement learning for behavioral modeling, by Jill O'Reilly and Hanneke den Ouden
Reinforcement Learning course, by David Silver
Understanding the bias-variance trade-off, by Scott Fortmann-Roe
Statistics vs. machine learning, fight!, by Brendan O'Connor
Cognitive maps in rats and men, by EC Tolman
The misbehavior of organisms, by Keller Breland and Marian Breland
The Americanization of mental illness, by Ethan Watters
On being sane in insane places, by DL Rosenhan
Parable of the Polygons, by Vi Hart + Nicky Case

'Quantum' theory of accountability, by Neil Lawrence
Teaching in prison, by Christia Mercer

What is an F-stop, by Matthew Cole
Brightness, luminance and confusion, by Charles Halsted

Against interpretation, by Susan Sontag
Shadow cities, by Andre Aciman
The end of solitude, by William Deresiewicz
A brief rant on the future of interaction design, by Bret Victor