The problem is that he is only learning when it negatively affects him. Plenty of people have already learned many of these lessons, he just has no interest in listening to them.
Sure. But if the only way Elon can learn why something is bad is through first-hand experience, will he act against speech that threatens minority groups he's not part of? What about those that are economically disadvantaged?
You can already see this lack of empathy at work in how he's trying to claw back severance he owes Twitter's ex-employees.