Looking back four or five years ago, do you feel stupid in some decisions you made or things you said? If you do, that’s a good signal. It means progress.
Anyone who’s leveling up feels stupid while looking back — which is totally normal — because back then didn’t know something. If you’re pushing yourself to the top hat’s inevitable.
So, knowing that in four or five years from now you’ll feel stupid about things you do or say today, what can you do to make it faster so you can make that change happen in a few months or couple of years? I believe asking yourself the following question is a nice habit to have:
What will make me feel stupid in the future?
Then you can have a whole new conversation with yourself and find some clues along the way where you need to put some thought and effort.