I’ve never really got that story. I understand it as a metaphor, but to me it doesn’t quite work because this problem can be solved rather easily by constructing something, anything, at the peak to hold the boulder from tumbling. If he places the rock in exactly the same way each time, no wonder it falls down. But he should at least try a different approach or any other trick that improves the chances of it working. There are plenty of options.

Granted, I never read the actual story, I’ve only pieced it together from the many pop culture references to it. So they may be other aspects of the story that I’m missing.