Antifragile by N N Taleb. Additionally also the black swan by the same author.
All said and done I feel like it's made me look at and evaluate a lot more possibilities at all important junctions in my life (if not all junctions). It's helped me channelise my mind better to understand signals I care about in an otherwise extremely noisy world. It's also made me a stronger individual being able to do more for people and look at things sometimes as just a series of outcomes, and making everyday life and outcomes more tolerable for me emotionally as well.
Antifragile has changed the way I've thought about many things. A couple key concepts in the book are like lenses that gave me entirely new ways of viewing the world.
The Lindy effect: The strongest systems are usually the ones that have been around the longest. Accordingly, there should be a healthy distrust for any recent invention or practice.
The world is too complex to understand: Complex systems are mostly not designed, but exist and thrive by virtue of natural selection. This includes human societies. Even leaders and managers of these systems do not understand why they work. In particular you can't predict the outcome of tampering with complex systems, and you should avoid doing it in a wholesale centralized way.
Stress makes antifragile systems stronger: In particular a certain amount of stress, challenge, and variation is necessary for a person to remain strong.
Extreme tails: Fragile and antifragile systems often have payouts where a single event dominates the outcome. As an individual, there are two takeaways. There are only a couple of opportunities in life that count. They will only count if you maintain the optionality to take advantage of them. A single tragedy can ruin you. You have to look out for it constantly, even if everything has been pretty rosy up until now.
All said and done I feel like it's made me look at and evaluate a lot more possibilities at all important junctions in my life (if not all junctions). It's helped me channelise my mind better to understand signals I care about in an otherwise extremely noisy world. It's also made me a stronger individual being able to do more for people and look at things sometimes as just a series of outcomes, and making everyday life and outcomes more tolerable for me emotionally as well.