He has a chapter that speaks to the topic of my recent essay on when to defy orthodoxy. His answer depends on whether you have skin in the game, meaning that there are personal adverse consequences if you are wrong.
If you have skin in the game, then Taleb would say that you are entitled to challenge orthodoxy, and indeed you should. People with skin in the game who defy orthodoxy are free. People with skin in the game who do not defy orthodoxy are slaves. So working for a large corporation makes you a slave.
Without skin in the game, you cannot be a good person no matter what you do. If you do not defy orthodoxy, you are a toady, trying to get ahead by going along. You are a journalist or academic who repeats what other journalists or academics are saying. If you defy orthodoxy you are dangerous, because without skin in the game you are risking other people’s lives and other people’s money but not your own. You are a banker taking in huge bonuses from bets that pay off in the short term, and when the bets turn sour you are long gone.
At least, that is how I read what he is saying.