BOTH of them have the curse of knowledge - failing to understand one that does not, the one that never experienced it and also forgot its struggles - for instance, I simply don't know the full picture before I do (and then the successful ones spreading their false experiences, peak-end bias of how they ended up happy to the strugglers!) And they may also have forgotten the adversities of the past.
Hard for a teacher to understand one who does not know. It's entirely normal, though. Plus, both ways, too little can be done.