I’m going to stick to the metaphor as literally (!) as I can… I’d say you can’t get to Athena without getting around Medusa first, that’s why she’s on the front of the shield. Once you’ve done it, I think you might be in good shape for the future — like getting around any threshold guardian maybe? Once you see them for what they are, they lose their fearsome aspect.
I like the phrase “simply to philosophize”. Seems to me, if you’re actually engaged in “philosophy” then that’s the one specific time you *don’t* need to worry about being turned to stone. :^) That kind of philosophizing requires maintaining a recognition that you don’t know everything you think you know and… finally, a state of wondering or wonder. Those alone usually prevent getting fossilized. :^)