Erik Torenberg wrote a post I wish I could have read when starting my career. It would have helped me figuring out how to pick companies to work at, people to work for, and companies to start: "[T]he biggest career mistake young people make is that they’re afraid to look dumb, so they follow safe paths to cap their downside, not realizing that they cap their upside too as a result. And said paths are often tournament-style competitions, perhaps not as safe as one would think."