It's always hard. Doesn't mean squish yourself with some preconception of normality, expectations. Predicting things about yourself from limited data you can't analyze in entirety is a hard problem, because the actual history of an experience always contains more information than you were able to aggregate at the time. So we refine, filter, get a perspective of ourselves. That judgement is impossible to make accurately.
It's like trying to bite your own teeth. It's always balancing act. Partially judgement, partially pushing boundaries. Letting one overtake the other, I mean, if judging is what you like doing, go you. But sometimes you just have to take action instead. You can't get better at anything without doing at least that.