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Why is it so hard as parents to teach our kids that mistakes are okay?

I think there are two reasons for this. First, I think there is terrible pressure on parents to have most excellent children, both for the protection of the child and for the ego of the adult. We want our kids to learn to avoid mistakes for then they will avoid embarrassing themselves and us. But, by doing so, they will also avoid potential psychological growth spurts. Second, in order to truly convince kids that mistakes are okay, we have to model for them being okay with our own mistakes. The critical issue is, however, we have to be okay with our own AWFUL mistakes, and it takes considerable courage to allow our children to witness our efforts to embrace our cringe-worthy errors.

What about those times when we do something "wrong" and we know ahead of time that it is wrong?

Nietzsche had a concept he called "self-overcoming" which captures a healthy way to look at this type of mistake. He believed that much of our energy is spent in trying to overcome both the unhelpful pressures of our social environment and also our internal tendency to feel overwhelmed by life. When we know better than to do "X", but we do "X" anyway, we have failed in our self-overcoming. In other words, we have given in to the temptation of "X" because we were out of energy. The particular type of energy we were out of is will power. Therefore, the conclusion to draw when we knowingly do something "wrong" is that we need to pay attention to our level of willpower in order to shore up our efforts to self overcome.

What about careless or thoughtless mistakes? Shouldn’t we be ashamed of making those types of errors?

My answer to this excellent question will reveal a couple of my biases. First, I believe utterly that we should never feel ashamed because that feeling is the result of experiencing shame and shame blights human existence. If you haven’t read “Shame: The Monster Under the Bed,” please stop what you’re doing and read it! Second, I also firmly believe that readers of this website are both thoughtful and careful, so I often leave off addressing everyday sloppy behavior. But to answer your question, occasional careless, thoughtless mistakes are part and parcel of being a human. Apologize where needed, debrief yourself carefully and move on. A person exhibiting a pattern of this type of error, however, is moving ever so surely away from good mental health. If you find yourself slip-slidin’ away from careful, thoughtful behavior, please take some time to read up on empathy, effective defense systems and kindness.