Gather initial thoughts and broad opinions about the book.

1. De Mello’s style is very direct and confrontational. Did you find his use of sharp humor and provocative statements engaging or off-putting? How did your feelings about his oratorical “dance” evolve?

2. The idea of “waking up” is central to many spiritual traditions. If you’ve read other works on this theme, like Eckhart Tolle’s The Power of Now (1997), did de Mello’s approach feel more challenging than these other authors? Why or why not?

3. Throughout the book, de Mello uses many anecdotes and parables to illustrate his points. Which story stuck with you the most, and what made that particular story so memorable or insightful for you?

Encourage readers to connect the book’s themes and characters with their personal experiences.

1. De Mello argues that much of people’s identity and emotional reactions are the result of societal “conditioning.” Can you think of a strong belief or value that you later came to see as a product of your culture or upbringing? How does your experience connect with de Mello’s idea of “unlearning”?

2. How does the distinction between the observing “I” and the conditioned “me” resonate with your own inner experience? Think of a time when you were able to watch a strong emotion or thought pass by without completely identifying with it. How did that perspective alter your actions in the moment?

3. De Mello draws a sharp distinction between an attachment (the belief that you need something in order to be happy) and a simple preference. Where in your daily life do you notice this difference playing out?

4. Consider de Mello’s four-step program for dealing with negative feelings. How might applying these steps change how you approach a minor, everyday frustration?

5. De Mello’s claims that even charity is a form of self-interest. How does this idea challenge your own understanding of altruism?

6. De Mello’s distinction between loneliness and “aloneness” defines solitude as a state of strength. How does this idea challenge or affirm your own experience of being by yourself?

Examine the book’s relevance to societal issues, historical events, or cultural themes.

1. De Mello heavily critiques society’s definition of success, suggesting that chasing status and approval is a form of addiction. How relevant does this critique apply to today’s world of social media and “hustle culture”?

2. De Mello identifies the need for approval as the ultimate “drug” that society uses to keep people “asleep” and controlled. What modern institutions, technologies, or cultural trends are as the primary “dealers” of this drug today?

3. The final parable warns that without the “fire” of direct experience, religion becomes nothing more than empty ritual. Where else, outside of formal religion, do you see this dynamic at play?

Dive into the book’s structure, characters, themes, and symbolism.

1. De Mello argues that grief stems from dependency (the belief that your happiness depends on another person). How does de Mello’s detached, philosophical perspective compare to other explorations of grief, such as C. S. Lewis’s raw account in A Grief Observed (1961)?

2. Awareness delivers its ideas in a circular, repetitive way rather than as a linear argument. How does this structure affect the persuasive elements of the presentation?

3. The fable of the crocodile concludes that life is cruel and arbitrary. What purpose does this story serve within the book’s larger spiritual message? How does it contribute to the idea of waking up?

4. De Mello warns that concepts can be barriers to reality. How does de Mello use metaphors and stories to break through this conceptual barrier?

5. The distinction between the “I” and the “me” is central to the book’s method. How do de Mello’s guided observation exercises work to create an experience of this separation, moving it beyond a purely intellectual idea?

Encourage imaginative and creative connections to the book.

1. De Mello’s four-step program for wisdom is designed as a practical tool. If you were to create a simple app or a pocket-sized journal to help someone practice these steps, what would you call it, and what key features would it include?

2. De Mello uses the image of a sailboat effortlessly catching the wind to describe change through awareness, contrasting it with the effort of pushing a broken car. What new metaphor or parable might illustrate this same distinction between effortless understanding and forceful self-improvement?

3. Imagine that you had the chance to attend one of de Mello’s live conferences. What question would you ask him about his teachings, and what challenging or story-based answer do you imagine he would give you?