Gather initial thoughts and broad opinions about the book.

1. The book’s core idea is the distinction between living in “The GAP” and “The GAIN.” Before reading, had you ever thought about your happiness or success in these specific terms? How has this framework changed the way you view your own progress and goals?

2. How did you find this book’s practical advice compared to other popular books on habits and mindset, like James Clear’s Atomic Habits (2018)? Do you see the “GAIN” mindset as a foundation for measuring progress and creating greater well-being, or as a separate tool for personal development?

3. After finishing the book, what was the most memorable story or concept for you? Was it a case study like Dan Jansen’s Olympic win, a psychological principle like the “hedonic treadmill,” or a practical tool like the “3 Wins Daily” practice?

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

1. The authors use the story of Edward, the investor who constantly moves his financial goalposts, to illustrate GAP thinking. Think about a professional goal or a personal project in your own life. Have you ever found yourself in a similar cycle of discounting your achievements because you were already focused on the next “ideal?”

2. A central practice in the book is the “3 Wins Daily” exercise, which encourages readers to reflect on their achievements and progress each day. Have you ever tried a similar gratitude or achievement-tracking practice? If so, what was your experience, and if not, what do you think the potential benefits or challenges would be for you?

3. Dan Jansen’s story illustrates the shift from a desperate “need” to a chosen “want.” Think about a current ambition you hold. Does it feel more like a harmonious “want” that energizes you, or an obsessive “need” that creates pressure?

4. Have you ever consciously tried to define your own “success criteria,” as the book suggests with Dean Jackson’s prompt, “I know I’m being successful when…?” How might creating such a list free you from comparing yourself to others?

5. The book introduces “mental subtraction,” where you imagine your life without one of your GAINS to increase your appreciation for it. If you were to try this exercise right now with a relationship, skill, or accomplishment, what new perspective might it give you?

6. Reflecting on your own skills, what is something you do now naturally and confidently that was once a major struggle? How does intentionally remembering that starting point change how you feel about your current ability?

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

1. The authors critique the American ideal of “the pursuit of Happiness,” arguing it traps people in the GAP. Do you agree with this interpretation? In what ways does our culture encourage us to see happiness as a future destination rather than a present state?

2. Where do you see the pressure to use external “reference points” most strongly in today’s world? The book points to education and social media, but are there other areas where social comparison may encourage people to measure themselves against external standards?

3. The GAP and GAIN framework was developed in the high-stakes world of entrepreneurial coaching. How does the book’s advice translate to contexts outside of business and elite performance, such as in caregiving, creative arts, or everyday personal growth?

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

1. How effective was the book’s structure, which first deconstructs the problem of the GAP and then provides a series of concrete tools for living in the GAIN? Did you find this progression from theory to practice persuasive?

2. The book balances scientific research, like the broaden-and-build theory, with personal case studies, such as those of Howard Getson and the Nortons. Which form of evidence did you find more compelling in supporting the authors’ arguments, and why?

3. What is the role of co-author Dr. Benjamin Hardy in shaping the book’s message? How do his personal reflections and expertise as a psychologist help make Dan Sullivan’s coaching concepts accessible and relatable to a broader audience?

4. Dan Sullivan often uses memorable, trademarked terms like “The Experience Transformer®.” What is the effect of branding these psychological tools? How does this naming strategy influence the way readers understand, remember, and apply these psychological tools?

5. Throughout the book, the authors use simple visual metaphors, beginning with the flip-chart diagram created for the client Bob. How do these simple illustrations help clarify the psychological dynamics of the GAP and the GAIN?

6. How do the core ideas in this book compare to Carol Dweck’s concept of a “growth mindset” in her book Mindset (2006)? Do you see the GAIN framework as a specific application of a growth mindset, or do they represent two different approaches to personal development?

Encourage imaginative and creative connections to the book.

1. Imagine you’re tasked with creating a one-hour workshop for students based on this book. Which single concept or exercise, like defining “success criteria” or the “5 Minutes in the GAP” rule, would you make the centerpiece of your session, and why?

2. The book features several case studies, primarily from business and sports. If you were to add a new chapter with a case study from a different walk of life, such as an artist, a teacher, or a new parent, how would their story illustrate the journey from the GAP to the GAIN?

3. If you were to design a simple app to help people practice the principles from The Gap and the Gain, what would its most important features be? How would you design it to encourage consistent use instead of turning the practice into another source of pressure or comparison?