Lives Wasted And Well-Lived: An Analysis Of Tolstoy’s The Death Of Ivan Ilyich

What if you did everything right and discovered on your deathbed that you've wasted your life? Rabbi and author David Wolpe talks about Tolstoy's The Death of Ivan Ilyich with EconTalk's Russ Roberts. Weaving Rabbi Wolpe’s own brushes with mortality and his years at the bedsides of the dying into Tolstoy's masterpiece, they talk about the lies we tell ourselves about death, our longing for honesty and human touch at the end, and the way that death forces us to take a clear-eyed look at life. They conclude by offering advice on how we can avoid Ivan’s regrets.

Listen to the episode here.

ABOUT THE SPEAKER

Named The Most Influential Rabbi in America by Newsweek and one of the 50 Most Influential Jews in the World  by The Jerusalem Post, and twice named one of the 500 Most Influential People in Los Angeles by the Los Angeles Business Journal, David Wolpe is a scholar-in-residence of the Maimonides Fund and the Max Webb Emeritus Rabbi of Sinai Temple. Rabbi Wolpe has taught at Harvard, the Jewish Theological Seminary, the American Jewish University, Hunter College, and UCLA.

RELATED SOURCES

• David Wolpe at Sinai Temple
• The Death of Ivan Ilyich and Other Stories by Leo Tolstoy
• The Denial of Death by Ernest Becker 
• Anna Karenina by Leo Tolstoy
• Staring at the Sun: Overcoming the Terror of Death by Irvin D. Yalom
• "Good Creatures Do You Love Your Lives" by A. E. Housman at AllPoetry
• "The Legend of Saint-Julian the Hospitaller" by Gustave Flaubert at The Literature Network
• "Yom Kippur Is a Reminder of How to Live" by David Wolpe in The Free Press, September 18, 2026
• "The Summer Day" by Mary Oliver 
• Addiction, Faith, and the Limits of Willpower (with Meghan O'Gieblyn) — EconTalk
• Paul Bloom on Happiness, Suffering, and the Sweet Spot — EconTalk
• Lives and Deaths: Essential Stories by Leo Tolstoy, translated by Boris Dralyuk 
• Richard Gunderman on Greed, Adam Smith, and Leo Tolstoy — EconTalk
• Ben Sasse on Faith, Family, and Facing Death — EconTalk