It's not so much the contradictory expectations that bother me, it's how success and failure are framed in modern society. The messaging is that for cis white men success should be externalized and failure should be internalized while for everyone not cis white and male it's the opposite. The messaging is that the system is built for the benefit of cis white men so when they succeed it's because the system pushed them to success and when they fail they do so in spite of the system pushing them to succeed so their failures are do to some particular flaw within themselves. The system is built for the benefit of cis white men so when someone who isn't cis white and male succeeds they do so despite the system pushing them to fail so the success is because of some special strength within themselves and when they fail it's because the system pushed them to failure.

There is truth to the premise that the system is built for the benefit of cis white men but the system doesn't push cis white men to succeed, especially not poor and working class men. It does give cis white men advantages but it does so primarily by creating additional barriers for people who aren't cis white and male. Your parents economic status is the most reliable indicator for success.