I still worry about the pain of future embarrassment, but I'm more likely to point out to myself that it's not a valid objection and I should do X anyway.

I HATE when it happens to me, it's the most stupid heritage of our undercortical brain. I argue with my brain all the time because of this...
Anyway:

Silly plan for taking over the world: Arrange to meet high status-people and offer to give their children swimming lessons. Gain their trust. Proceed from there.

A possibly even better plan is to start an image consulting business.
Recently a book came out here in Italy, it was titled "The powerful men whisperer" (yeah, I know, even translated it's that bad) and retold the story of the head of a PR consulting organization, and how through that business he became the trusted friend of basically every top manager, prime minister or other powerful person in the last twenty years, while at the same time being able to remain thoroughly anonymous.