In episode 401 of This American Life, David Segal interviewed Rebecca Gee, whose mother, Elizabeth, a devout Mormon, had died of cancer in 1991 when Rebecca was sixteen. Elizabeth, knowing she would not be part of her daughter’s growing up, decided to write Rebecca letters that she asked her husband to mail every year on Rebecca’s birthday. Initially comforted by her mother’s letters, Rebecca found that, over the years, they were not always easy to read. As she matured, she found herself less connected to her Mormon upbringing, so when she read her mother’s words telling her to remain true to her Mormon faith, Rebecca felt a moral dilemma. Her devout mother’s words did not speak to who she was, and she felt that, though her mother had died, she was still disappointing her.

I mention this story as a cautionary tale for those of us writing to our children, grandchildren, and others to share our values, wisdom, guidance, and love.

This tradition of writing our legacies is not new to us as Jews. In medieval times, parents wrote tze-vah-oat (commandments) in the form of letters to their children to pass on their ethical values and ritual precepts, their Torah. These letters, referred to as “ethical wills,” were often left to be read after the author’s death, like the letters Rebecca received from her mother.

So, how do we share our wisdom, experience, and love in ways that do not make our loved ones uncomfortable? I learned from my father that how we show up on the page matters. When I was fourteen, he handed me an ethical will he had written to me and my three younger siblings. In this letter, he showed up not as a rabbi directing us but as a father writing from his heart, putting himself on the page in a more vulnerable way than he had ever spoken to us in person.

He stated his hopes: “Respect one another, even if love is not always possible. Take care of each other … always.” He wrote about disagreements: “As you grew older, we differed concerning substantive matters, and I was proud of how you all stood your ground, even when I attempted to intimidate.” He wrote about how he might pick on us when we behaved like him, “at least … those aspects of myself that I liked least.” He challenged us to recognize our own weaknesses so we could turn them into strengths. He asked us to remain proud Jews, to care for our mother, and to say kaddish for him, when he died.

My father wrote as if this were his last letter to us, stating what he most wanted and needed to say. This letter changed my life. Even today, over four decades later, I return to it when I feel the need to hear my father’s voice and his wisdom in a deep and loving way.

My father’s letter motivated me to write honest and vul-nerable letters to my son, Gabe. One in particular stands out. After visiting Gabe in Israel during his sophomore year of high school, I wrote to him to reflect on and reiterate a conversation we had on a Shabbat afternoon. My letter spoke not only about the content of our talk but also about the fact that we had such a meaningful and honest conversation, and that I hoped these conversations would continue. I was in the midst of a midlife struggle, and I had shared some of my life learnings with him. He, in turn, had shared some of his life learnings with me. It was during this conversation that I encouraged him to live his own life, not the life he believed others wanted him to live.

We can share our wisdom, experience, guidance, and love in many ways. Letters are particularly impactful because we can read them on our own time. We can return to them when our souls need to hear the messages contained within, and we can hold them not only in our hearts but also in our hands. Letters like these create opportunities for conversations, and they are invitations for both readers and writers to learn more about themselves, each other, and the relationship they share. This learning gives us the chance to deepen, heal, strengthen, and uplift our relationships while we’re still here to enjoy them.