The Complexities of Teaching the Virtues of Honesty: A Grandmother’s Dilemma

As Grandparents Day 2026 approaches – this year falling on September 13, the second day of Rosh Hashanah – I find myself reflecting on the virtues of honesty. On Rosh Hashana, we Jews are mandated to move beyond self-deception and pursue radical honesty about the people we have been this past year. But, coincidentally, just recently, I have been wondering whether, in imparting life values to my grandchildren, “Is it wise to tell them that honesty is always the best policy?”

Honesty is in my DNA; I find being honest a more comfortable way to go through life. And I’m sure that those who know me would say I greatly value getting honest feedback from others. So, consistent with my nature, I’ve always told my grandchildren that it is very important to be honest – and I’ve asked them never to lie to me.

The truth is, though, that being honest doesn’t always lead to happy endings. Sometimes I inadvertently hurt others when I choose honesty above all else. By the same token, I sometimes get hurt by asking for total honesty from others. And yet, I automatically persevere in making honesty a priority.

I’m glad to say that Judaism, at least in its principal teachings, endorses my preference. As the late Dr. Meir Tamari, founding director of the Center for Business Ethics and Social Responsibility, wrote in the Orthodox Union’s magazine Jewish Action: “Honesty is not just another aspect of Judaism, but is of its very essence . . . . The Torah, the Prophets and the Psalmist describe the God-fearing man almost exclusively as one far removed from all forms of falsehood or dishonesty.”

In researching other Jewish sources to see what scholars, ancient and modern, have said about honesty as an overarching value, I came across a wonderful essay by musician, content creator and entrepreneur Noey Jacobson on the website Unpacked. Jacobson poses the question, “What is so bad about telling little lies?” And he responds by citing the wisdom of a 13th-century rabbi named Jonah Gerondi: “A person who accustoms his tongue to speak falsehood about a matter that has neither a loss nor gain will, when he comes to speak matters of principle, not be able to speak the truth; as it is his mouth that will speak and habit rules over it.”

Building on this quote,  Jacobson explains, “Small lies don’t stay small. They’re habit-forming, at which point the lies become bigger.” He also cites modern research that reveals “telling small lies makes it easier for people to tell bigger lies because the amygdala, the part of the brain that would normally put the brakes on a lie by making a person feel uneasy, gradually becomes desensitized to deception. Small lies literally change the constitution of your brain.”

But, Jacobson says, Judaism allows fibs if we do so to avoid hurting others and there will be no further harm caused by that little lie. He concludes with the caveat that we must keep asking ourselves three questions: “Are we pushing ourselves to strive for truth as much as humanly possible?” “Do we understand the value of truth-telling as a way of maintaining our integrity and connecting us with others?” and “Are we willing to sacrifice to protect that value?”

These are good questions to mull over in a contemplative moment. But, for a grandparent (or a parent) this sort of self-reflection is simply too complex to teach little children. It’s easier to say to a child, “You must always be honest.”  The problem comes, though, when  honesty is actually the cruel choice –like telling another child who wants you to play his “awesome” new game that it is dumb and you don’t want to play.

As Talmudic and Rabbinic Professor Jeffrey L. Rubenstein notes in his article on ReformJudaism.org, “Jewish tradition emphasizes the importance of telling the truth, but not always.” He quotes Rabbi Eliyahu Dessler (1892-1953), who says, “Sometimes it is necessary to deviate from the truth, such as when the truth will not help but will cause injury.”

Rabbi Dennis S. Ross, in his article on ReformJudaism.org entitled “When Can We Lie With a Clear Conscience?” explains that, though the Torah wants us to tell the truth, “it also includes stories of lies to show that there are times when even a Torah of truth realizes that some lies serve a higher moral purpose.”

So when can we start teaching these sort of nuances to young children? Maybe it’s never too early, even if the nuance goes over their heads; a seed will be planted and, eventually, our teachings will click.

Recently one of my granddaughters, age nine, called me on FaceTime. She has been doing that more often lately. Out of curiosity, I decided to ask her, “Do you call me because your mom tells you to call?” Hesitating to answer for a few seconds, she then replied, “Yes, my mom tells me to call.” Impulsively, I reacted, “Ohhh! That’s disappointing!” A look of discomfort filled her face. I had told her never to lie to me but now her honest answer disappointed me. As I pondered what to do about the inner conflict I’d created for her, she surprised me by adding, “Well sometimes I call because I think about you!”

Even though she may not have been able to articulate the concept, she clearly sensed that honesty, though an important trait, isn’t the best choice all the time. And she was even perceptive enough to add a comment to make me feel better.

Hopefully, eventually, all our grandchildren will come up with a nuanced policy of intermingling the need to be honest with the desire to be kind and to do no harm. And they will have crafted a way of life of which they can be proud.

The author does not speak on behalf of Hadassah and the views expressed herein are the author’s own and not necessarily those of Hadassah.

Lonye is a member of the Hadassah Writers’ Circle, a dynamic and diverse writing group for leaders and members to express their thoughts and feelings about all the things Hadassah does to make the world a better place. It’s where they celebrate their personal Hadassah journeys and share their Jewish values, family traditions and interpretations of Jewish texts. Hadassah members are proud of their Zionist mission and their role as keepers of the flame of Jewish values, traditions and beliefs as well as advocating for women’s empowerment and health equity for all. Since 2019, the Hadassah Writers’ Circle has published nearly 800 columns in The Times of Israel Blogs and other Jewish media outlets. Interested in writing? Please contact hwc@hadassah.org.