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The Monk and the Riddle book club questions
Here are 11 book club questions for The Monk and the Riddle by Randy Komisar, ordered to open easily and end somewhere worth arguing about. Copy them, print them, or bring them up one at a time.
Randy Komisar spent years as a virtual CEO and partner at Kleiner Perkins helping founders build companies, and The Monk and the Riddle draws on that experience to make a case about what startup culture gets badly wrong.
Randy Komisar · 2000 · 3h 45m
Full summary and key takeaways →The 11 questions
- 1.
Komisar's Deferred Life Plan is the idea of suffering now to live later. Be honest: to what extent is your current work a version of that plan?
- 2.
He draws a distinction between passion and mere interest. By that standard, what work would you call a genuine passion, not just something you're good at or that pays well?
- 3.
The protagonist Lenny is pitching a business he doesn't care about. Have you ever committed significant effort to a project you weren't personally invested in? What motivated you, and how did it end?
- 4.
Komisar argues that founders without intrinsic connection to their work make worse decisions under pressure. Do you agree? Can you think of counterexamples?
- 5.
The book is sympathetic to entrepreneurs but skeptical of the financial-exit-above-all culture. Where do you think the right balance is between financial ambition and meaningful work?
- 6.
What question would you want a mentor like Komisar to ask you before you committed to your next major career move?
- 7.
The book was published in 2000 at the height of the first internet bubble. How does its critique of Silicon Valley culture hold up now, a quarter-century and several bubbles later?
- 8.
Komisar says the goal is work you'd do even knowing you might fail. What work in your life meets that bar, and what keeps you from pursuing it more directly?
- 9.
The parable format lets Komisar make direct claims about meaning and work without seeming preachy. Does the story device work for you, or does it feel like a shortcut?
- 10.
Hawk, the mentor figure, has made a life outside the conventional startup path. What trade-offs does that life entail, and would you make them?
- 11.
If you had to name one thing you are currently deferring that you tell yourself you'll get to eventually, what would it be? What would it take to start now?
How to run the discussion
- Pick six to eight, not all of them. An hour of real discussion covers fewer questions than anyone expects, and racing the list is what makes a book club feel like homework.
- Open with what people noticed, not what they concluded. Asking for a verdict first hardens opinions before anyone has heard each other.
- Let the disagreement run. The questions below that split a room are the ones worth the time; the ones everyone answers the same way can be skipped.
- Ask the quiet person a specific question. A direct, narrow question is far easier to answer than an open invitation to contribute.
Themes worth steering toward
If the conversation stalls, these are the threads that usually restart it.
Common questions
What are good book club questions for The Monk and the Riddle?
Here are 11 book club questions for The Monk and the Riddle by Randy Komisar, ordered to open easily and end somewhere worth arguing about. The strongest openers ask what each reader noticed rather than what they concluded, and the discussion usually turns on entrepreneurship, purpose and meaning, silicon valley culture.
How long should a book club discussion of The Monk and the Riddle last?
Most groups run 60 to 90 minutes of actual discussion. That is roughly six to eight questions, not all of them, so pick the ones that suit your group rather than working down the list in order.
What are the main themes in The Monk and the Riddle?
Entrepreneurship, Purpose and meaning, Silicon Valley culture, Deferred life, Work and identity. Those are the threads most likely to divide a room, which makes them the useful places to steer a discussion that has gone quiet.
Picking the next one? See books like The Monk and the Riddle or questions for other book club picks.
