1. What is the connection between death and life in The Death of Ivan Ilyich? More specifically, how and why is it suggested that an understanding of death is important to an understanding of life?
2. How does Ivan’s relationship to his own death change over the course of the story? At what particular moments can you see this change taking place?
3. What does death actually mean in The Death of Ivan Ilyich? Are there different kinds of death? And what does Ivan mean when he says, “Death is finished”?
4. What markers does Tolstoy give to show that Ivan and his family are part of the middle class? Be specific.
5. What are the characteristics of the Russian middle class as Tolstoy portrays it in The Death of Ivan Ilyich?
6. What is this propriety that seems to be so central to Ivan’s social set? What kinds of things are proper to them? Why does Tolstoy seem to think there’s something false about this?
7. Is Tolstoy's depiction of the middle class believable, or too exaggeratedly negative and satirical?
8. Before his sickness, what does Ivan Ilyich think happiness is? What are the things that make him happy?
9. Why is it that Ivan Ilyich’s former joys appear false to him once he becomes ill? Does the fact that they do not console him while he is dying mean that he wasn’t really happy earlier in life?
10. Why does Ivan Ilyich find the only happiness of his life in his childhood?
11. Tolstoy seems to tell us much more about false happiness than about real, genuine happiness? Does he give any indications as to what genuine happiness is?
12. Why does Ivan’s act of communion make him think of his appendix?
13. Do you think Ivan could have grown closer to his family during his illness if he’d acted differently? Or was it a lost cause from the beginning?
14. What is it about his doctors that reminds Ivan Ilyich of his own profession as a lawyer?
15. How does Ivan Ilyich’s relationship to his doctors evolve over the course of the story? Cite specific examples. Is that change connected to larger changes within his character?
16. What is it about doctors that Ivan finds false?
17. What does it mean to be false in The Death of Ivan Ilyich? Are there multiple ways of being false?
18. Do you think that Ivan is aware of the falseness in himself, or does he only see it in others?
19. How is the refusal to face death related to the other kinds of falseness in the book? How is this displayed in particular characters?
20. Does Ivan’s suffering have a purpose? What makes you think it does or doesn’t?
Adapted from Shmoop.com