Shlomo HaMelekh, the wisest of all men, tells us: Do not rebuke a scoffer, lest he hate you; rebuke a wise man, and he will love you.
The surface level interpretation of this is simple. A scoffer doesn’t want to hear rebuke and, so, when you rebuke him, he will hate you. A wise person, on the other hand, is always looking for an opportunity for growth. When you rebuke him he will love you since you are pointing out a flaw in a certain area and giving him an opportuniy for additional growth.
The Shelah has a deeper interpretation of this verse, The Shelah explains that the verse doesn’t speak about two different types of people being rebuked, it speaks about two different ways of giving rebuke. One way of rebuking is something like this: “You are disgusting! You have some nerve behaving that way. You don’t know what you are doing. You better shape up.†By rebuking this way, the rebuker turns the one who is being rebuked into a scoffer and he will then “hate youâ€. The other way of rebuking is something like this: “You are a great person. You are a wise and introspective person with good middos. I’ve noticed something that doesn’t seem to fit with your good qualities. If you work on this issue, you will refine yourself even more.†By rebuking in this manner, the rebuker is making the one who is being rebuked into a wise man and he will “love you.â€
Rabbi Hadar Margolin in his HaSimchah B’Moadim (partially available in english as “Crown Him with Joyâ€) explains that this insight into giving rebuke is just as applicable when rebuking oneself, especially in the pre-Rosh Hashana teshuvah mode. The mishnah in Avos adjoins us: “Do not view yourself as a rasha.†Don’t regard yourself as a scoffer, “rebuke a wise man!†Tell yourself: “I am the grandchild of Avraham, Yitzchak and Yaakov. I have good qualities, I’m striving to grow. As such, it is incumbent upon me to improve myself in this particular area.†Such an approach motivates and stimulates improvement. The opposite approach, beating oneself up and degrading oneself can cause depression and lead one to think that he can never improve thereby creating a barrier to teshuvah.
Kesiva v’Chasima Tova.