Parental Guilt and Success
Living Jewish | February 28, 2026
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Parental Guilt and Success

Living Jewish | February 28, 2026

Question: I am the proud father of eight children, all of whom I love very much. Unfortunately, half of them have chosen to abandon the path of Chabad, some with Torah observance that is borderline at best. As a result—and with full awareness that I have made my fair share of parenting mistakes—I often feel that I have failed horrifically as a parent. How do you see my situation?

Answer: To begin with, you are wearing too many hats: prosecuting attorney, jury, and judge. You have built an “infallible and foolproof” case against yourself, declared yourself guilty on all counts (as you write, “I have failed horrifically”), and sentenced yourself to a lifetime of guilt, self-criticism, and misery.

Rabbi Jonathan Sacks, former Chief Rabbi of England, shared a powerful lesson. Holding up a sheet of paper with a single black dot, he asked his audience what they saw. Most answered, “a black dot.” Rabbi Sacks challenged them: why focus only on the dot, when the white space makes up 99% of the page?

You have not “failed horrifically as a parent.” Half of your children are following the path of Chabad, which appears to be your preference. The others maintain varying degrees of observance, still within the realm of some connection. Even if this were the only measuring stick to judge your success as a parent, any reasonable and objective observer would be hard-pressed to label you as a failure.

What truly stands out, however, is your opening statement: “I am the proud father of eight children, all of whom I love very much.” Regardless of the paths your children have chosen, you remain a proud father who loves each child deeply. That is beautiful—and it speaks volumes about your success as a parent. Your love is not conditioned on whether your children do what your want; you love your children for who they are. Kol HaKavod. Not every parent has reached your level.

“The steps of man are directed by G-d” (Tehillim 37:23). Our place in life, including our challenges, comes from Hashem. Does Hashem want us to live with guilt and misery, or to learn from the past and move forward with joy and purpose? We all stumble; this is part of our growth and learning. The key is to get back up—using the fall to reach even greater heights. And, a key step forward is appreciating the good that we have accomplished and the blessings that Hashem has given us.

Aharon Schmidt, marriage & individual counseling: www.aharonschmidt.com.

Question: I am the proud father of eight children, all of whom I love very much. Unfortunately, half of them have chosen to abandon the path of Chabad, some with Torah observance that is borderline at best. As a result—and with full awareness that I have made my fair share of parenting mistakes—I often feel that I have failed horrifically as a parent. How do you see my situation?

Answer: To begin with, you are wearing too many hats: prosecuting attorney, jury, and judge. You have built an “infallible and foolproof” case against yourself, declared yourself guilty on all counts (as you write, “I have failed horrifically”), and sentenced yourself to a lifetime of guilt, self-criticism, and misery.

Rabbi Jonathan Sacks, former Chief Rabbi of England, shared a powerful lesson. Holding up a sheet of paper with a single black dot, he asked his audience what they saw. Most answered, “a black dot.” Rabbi Sacks challenged them: why focus only on the dot, when the white space makes up 99% of the page?

You have not “failed horrifically as a parent.” Half of your children are following the path of Chabad, which appears to be your preference. The others maintain varying degrees of observance, still within the realm of some connection. Even if this were the only measuring stick to judge your success as a parent, any reasonable and objective observer would be hard-pressed to label you as a failure.

What truly stands out, however, is your opening statement: “I am the proud father of eight children, all of whom I love very much.” Regardless of the paths your children have chosen, you remain a proud father who loves each child deeply. That is beautiful—and it speaks volumes about your success as a parent. Your love is not conditioned on whether your children do what your want; you love your children for who they are. Kol HaKavod. Not every parent has reached your level.

“The steps of man are directed by G-d” (Tehillim 37:23). Our place in life, including our challenges, comes from Hashem. Does Hashem want us to live with guilt and misery, or to learn from the past and move forward with joy and purpose? We all stumble; this is part of our growth and learning. The key is to get back up—using the fall to reach even greater heights. And, a key step forward is appreciating the good that we have accomplished and the blessings that Hashem has given us.

Aharon Schmidt, marriage & individual counseling: www.aharonschmidt.com.

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