No one person had to understand everything about feudal society for the next stage to emerge. It just emerged, as always happens in an evolutionary process.
To try again with a more complete answer to your initial question:
Why is transhuman-ness or posthuman-ness a special exception for the to the general rule that surpassing (or at least passing) something does not in fact require understanding it?
In all the examples you’ve given, organic life is the common denominator. Each is a case of the natural progression of life, either the natural life cycles that have existed for billions of years, or of the culture that has emerged out of that.
If by “transhumanism” we mean a transition of human “life” (i.e, consciousness and culture) off our evolved biological platform onto some other recently or newly-created technology platform, someone would have to understand what human life actually is in order to make it happen or recognize that it has happened.
If we mean something else then people need to explain what they mean, but that’s really why we get stuck in the weeds on this topic; we don’t have a simple, agreed understanding of what it is we’re transitioning from/to and what is doing the transitioning.
But the simple answer to your central question is that the key difference here from the rule you’re positing is that we’re talking about a departure from the natural biological and cultural evolution that has brought us to this point.