Rabbis do the same thing with people trying to convert to Judaism, turn them away to see their real motivation. And indeed, if one single “NO” is enough for someone to give up it’s probably not for you.

However, it sometimes works the other way around, getting encouraged to do something make you realize you can (and sometimes should) do this very thing.

I always find it weird when i meet someone who prefers the first mindset over the second one. I believe that more positivity will lead to a better society. It doesn’t mean giving participation trophies, or lie about the reality of the journey at all — If someone wants to succeed they will need to sweat, cry and (hopefully not literally!) bleed a LOT— but as the popular quote says “Whether you think you can, or you think you can’t — you’re right.”