Yom Kippur invites us to confront our own mortality—symbolized by the white garments we wear, which resemble burial shrouds. This day is a rehearsal for our final judgment, where we assess our lives and consider our mistakes, much like the regrets. Recently, Dr. Shoshana Ungerleider—an internist—wrote an article regarding the top five regrets people have on their deathbeds and what they can teach us about living a healthier lifestyle. This theme ties directly into Yom Kippur—a day devoted to introspection, repentance (teshuva) and realignment with our values.
The first regret that her patients often mentioned was, “I didn’t spend enough time with the people I love.” No one ever hears a eulogy where they praise the deceased person for having spent hours and hours of overtime at their office, working hard. This regret resonates with the words of Rabbi Akiva, who famously taught that, “Love your neighbor as yourself,” (Vayikra 19:18) is a fundamental principle of the Torah. Relationships and community are at the heart of Jewish life, and neglecting them can lead to deep regret.
On Yom Kippur, we ask forgiveness not just from God but also from those we may have wronged. It’s an opportunity to reflect on how we’ve prioritized relationships in our lives. Did we cherish our loved ones enough? Did we take time to connect meaningfully, or were we too consumed by work or other distractions?
The second most common regret is, “I worked too much and missed out on life.” This regret calls to mind the Talmudic principle of balancing work with Torah study. Rabbi Yishmael taught: “Conduct yourself in a manner where both study of Torah and earning a living are balanced,” (Brachot 35b). Focusing too much on material pursuits at the expense of our spiritual and emotional lives is a common struggle. Yom Kippur allows us to reevaluate how we spend our time. It reminds us to return to what truly matters—not material success, but spiritual fulfillment, family and community.
The third regret that is often expressed is, “I let fear control my decisions and didn’t take risks.” In the Talmud, we find the story of Rabbi Eliezer, who delayed making teshuva because he thought he had more time. On his deathbed, he warned his students, “Repent one day before your death,” (Shabbat 153a). His message was clear: “Don’t let fear or procrastination prevent you from living boldly and meaningfully in the present.” We never know how much time we have, so we must seize every opportunity to live with purpose and integrity.
Fear of failure, uncertainty or the future often holds us back from taking spiritual and emotional risks. But Yom Kippur encourages us to confront those fears head-on. The day itself is about facing the uncomfortable truths of who we are—acknowledging our vulnerabilities and striving to change.
A fourth expressed regret is, “I wish I’d been braver in the face of uncertainty or opportunity.” This sentiment mirrors the famous story of Nachshon ben Aminadav at the Red Sea. While the Israelites hesitated—unsure whether to enter the sea—Nachshon stepped forward into the water, showing bravery and trust in God’s promise. His boldness brought about the miracle of the sea’s parting (Sotah 37a).
On Yom Kippur, we are encouraged to be like Nachshon. We are called to act with courage—to step into the unknown and to take the spiritual and emotional risks that lead to growth. Whether it’s making amends with someone we’ve hurt or taking on a new mitzvah, this day is about pushing past the limits of our comfort zones.
The final most common regret is, “I focused too much on the future and lost touch with the present.” Rabbi Shimon Bar Yochai taught that one should not worry excessively about tomorrow’s troubles, as we cannot know what the future will bring (Talmud Brachot 9b). Being overly concerned with the future can prevent us from living fully in the present—appreciating the blessings of today.
Yom Kippur is about being present. The day is long, and the prayers are intense—forcing us to slow down and reflect deeply on where we are in life right now. The fast, the confessions and the communal nature of the day all ground us in the present moment, reminding us that while we plan for the future, we must live fully in the present.
In essence, Yom Kippur offers us a powerful opportunity to address the very regrets that Dr. Ungerleider’s patients express at the end of life. By embracing the teachings of Jewish tradition—the importance of relationships, the balance between work and spiritual life, the courage to take risks and the focus on the present—we can begin the process of teshuva (or return) and ensure that we live lives of meaning and fulfillment.
As the Talmud teaches, the gates of repentance are always open (Avodah Zara 17a). Yom Kippur reminds us to walk through those gates now, while we still have the time.
Rabbi Dr. Avi Kuperberg is a forensic, clinical psychologist and a member of the American Psychology-Law Society. He is the coordinator of Bikur Cholim/Chesed at Congregation Torah Ohr in Boca Raton, Florida. He can be reached at [email protected].
