Fooled by Randomness - NN Taleb's counterintuitive thoughts on managing uncertainty
Training for the New Alpinism - Years before "Zone 2 training" became mainstream, Scott Johnston wrote about applying it and other techniques to become a better alpine climber
This Can't Go On - I often view events through a more zoomed-out lens of how they fit into broader trends or history. It's why I love learning about hunter gatherers
Do Things that Don't Scale - Classic Paul Graham post about doing things that won't scale but are useful in the initial stages
Refinement Culture - Culture is stagnating. The world is smoother and smaller than in the past. We domesticate ourselves more with each decade. I think this trend is much broader than what's discussed in the essay.