The problem with this philosophy is that it involves personal responsibility and accepting that decisions have consequences.
For example, suppose that you deliberately choose a lower-paying career. Within a few years, you find that you can’t afford things that people who chose the higher-paying career can buy. If you are a libertarian, you need to acknowledge that you chose the career and therefore have to accept the consequences. If you’re a socialist, then you think that the government should simply give you the things you want, but can’t afford.
Being a libertarian also require that you treat people as individuals, not as grist for the mill of identity politics. Libertarians generally believe that people succeed or fail based on their efforts. It’s more difficult than judging people based on skin color or sexual orientation (e.g., a black female who graduated from Harvard is more oppressed than a white male working in a coal mine in West Virginia).