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Sometimes, in order for one to learn, one must experience the failure of the ideas one believes to be true which are, in fact, not true. If the student in this process is a child or someone under the care of another, this process can sometimes be called "tough love."

Are there any Jewish teachings on this topic?

So, true love is often tough.

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Proverbs 13, 24:

יג,כד חוֹשֵׂךְ שִׁבְטוֹ, שׂוֹנֵא בְנוֹ; וְאֹהֲבוֹ, שִׁחֲרוֹ מוּסָר. ‏

He that spareth his rod hateth his son; but he that loveth him chasteneth him betimes.

חושך שבטו. מי שהוא מונע שבטו מהכות בנו ליסרו הוא שונאו כי מפני זה יהיה באין מוסר ומי שהוא אוהבו שחרו מוסר בקטנותו לחנכו במוסר על פי דרכו: (רלב"ג) ‏

Gershonides explains that a father who refrains from punishing his son, this father hates his son because the child will become rude.

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Whilst it is necessary to always treat children with immense love, there are sometimes occasions when parents must exercise what has become known as ‘tough love’. This means to do something for the greater good, at the cost of potentially upsetting the child. For example, all parents will at some point have to send their young children to the doctor to receive a vaccination. Naturally, the parent is looking out for their child’s long-term health and welfare, ensuring the prevention of any threatening disease. However, to the child this might appear as a betrayal of trust. How could their loving parent make them endure such a painful experience? In truth though, situations such as these hardly represent a test for parents as such action is the generally accepted protocol. However, it is with issues such as substance abuse that parents are confronted with major tribulations as to how to act. In a case like this, a parent is put in the heart-wrenching situation of wanting the best for their child without putting them in a hurtful position. Nevertheless, action must be taken if it is to curb self-destructive behaviour. This idea although hard to accept is a notion that is shared by the מדרש. We are told, "רשב״ל אומר כל מי שנעשה רחמן במקום אכזרי סוף שנעשה אכזרי במקום רחמן" – “Rabbi Shimon ben Levi says: All those who are merciful with the cruel, will come to be cruel to the merciful” (קוהלת רבה ז:טז). This means that whilst it is normal for one to be benevolent to a person they love; there are times when administering kindness will actually be more harmful than good. Ultimately, every parent has their child’s best interests at heart. If this means doing something necessary that will upset the child, whilst it may be painful, it is still crucial that it be acted upon.

It is inevitable that at some point in one’s live, a parent will have to take the harsher route, even in instances where it may seem that exercising tough love is never an option. For example, the תורה commands, “כל אלמנה ויתום לא תענון” – “You shall not afflict any widow or orphan” (שמות כב:כא). At first glance, it would seem that in such a delicate circumstance, a person must be very careful to show an elevated degree of sensitivity. Indeed, one would think that a person should greet such people with the utmost tenderness. However, the משנה תורה, הלכות דעות ו:י) רמב״ם) notes that it is important to find a subtle balance. For the most part, it is important to treat them with this higher level of compassion, but there are instances when even these people must be guided with a more stringent approach. The רמב״ם explains that a Rov is permitted to discipline them in order to teach them תורה, a craft or to set them on the straight path. Thus, even though one must predominantly treat the likes of orphans with care, it evidently must not come at the expense of over-indulgence. If one takes too muted an approach, orphans and the like will never learn how to take responsibility for themselves nor how to overcome the very real disadvantage that they have been faced with.

One example of the need ‘to be cruel to be kind’ is found in the הגדה with the ארבע בנים – The Four Sons. We are told concerning the wicked son, the רשע, that the best form of action is to “הקהה את שניו” – “blunt his teeth”. Many מפרשים mention the famous דבר תורה surrounding this text: The גמטריא of רשע adds up to 570. We are instructed to knock out his teeth; therefore if one takes the numerical value of (שניו (366 and subtracts it from the (רשע (570, one is left with a (צדיק (204 – a righteous person. Perhaps we can take strength from this idea. In times when one needs to exercise tough love, it can be an emotionally formidable task. A parent is likely to feel the burden of their predicament weighing down on their shoulders as they consider how best to approach the situation. However, with guidance and perseverance, the end result, with Hashem’s help, will be positive.

Also see Rabbi Twerski’s Not Just Stories: The Chassidic Spirit through its Classic Stories, (Shaar Press – 1997), pp. 136-137 has nice write up on this topic.

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