You're ignoring the fact that most highly paid positions come with a lot of bullshit. Depending on the position and company, that could be overwork, ridiculous politics, or the inability for your work to have any impact. I still make good money by my standards, but it's $65k less than my highest pay (cash, not RSUs). No regrets. I find your advice that somebody not maximizing their earnings "seek a therapist" a bit tone-deaf.