Our Gemara on Amud Aleph makes a statement about times when it is better not to argue with people who seem to insist they are correct, and will not be receptive to guidance, despite them being erroneous and sinful:
Leave the Jews alone; it is better that they be unwitting sinners and not be intentional sinners.
When it comes to family members who do what we believe is wrong, it is so hard to keep quiet and take the long game. It is embarrassing and an affront to our ego that those close to us would do the wrong thing.
Rav Chaim Volozhin is quoted in the Kesser Rosh (143, a compendium of Rav Chaim’s practices written by a loyal student) as saying that if a person does not believe it is in his nature to give mussar and rebuke in a gentle manner, then he is exempt from the mitzvah of tochacha.
In the recovery community there is a term, “living amends”. That is, sometimes circumstances prevent you from making a proper apology or obtaining forgiveness. However, one can live their life in such a way that makes amends. It actually is similar to something else we saw in our Gemara on 29a about those who are unsure how to return stolen goods from random people. They should engage in acts of public welfare so as to eventually benefit from whom they stole.
In any case, I would like to propose a term called “living admonition“. There are many ways people can learn from us and our behavior and they don’t really need us to throw it in their faces. Just by showing love and respect and involvement in the affairs of those whom we love, while still living our lives on the highest level of morality, it will offer many subtle reminders and corrections for proper behavior. The challenge is, how do you do this without unconsciously or semi-consciously having a holier than thou attitude? It is very difficult, and whatever degree your attitude leaks out, that is the degree in which you have compromised your effectiveness as both a Jew and a decent human being. I recommend studying chovos halevavos Shaar Yichud Hammase where he offers many ways to puncture self righteous rationalizations and mixed motives other than true humility and service of God. After you study that chapter, and you find yourself congratulating yourself for being so Pious for studying that chapter, read it all over again!
Translations Courtesy of Sefaria, except when, sometimes, I disagree with the translation 
Do you like what you see? Please subscribe and also forward any articles you enjoy to your friends, (enemies too, why not?)