I think yours is less a problem of how to keep up with the joneses and more a problem of realistically evaluating your circumstances and expectations.

Whoever is telling you that you aren’t good enough is trying to pull something over on you at this point. It works well on people that can never be satisfied.

I have no idea who is telling you that unless it's yourself. Contrary to the impression that some people here may give you, making millions a few (or even many) years out of school is not the norm wherever you went to school. And while connections do matter to some degree among Ivy and related grads I know (and those are mostly for what many here would consider low-paid jobs in the literary industry), connections from people I've worked with at jobs have always mattered to me more or even exclusively.

As I wrote, there is pedigree in some professions/positions but I'm assuming you're not looking at clerking on the Supreme Court, working for a white shoe law firm, and maybe getting a Federal Court of Appeals seat. Nor working for McKinsey.