Before reading this book, what did “the good life” mean to you?

Did Shakespeare’s characters and stories challenge or expand your personal definition? If so, in what ways?

The author argues that Shakespeare’s world is much like ours (full of political turmoil, division, illness, environmental destruction, etc.) and that his plays offer wisdom for handling life’s challenges. Do you agree with this comparison? Why or why not?

Shakespeare’s Guide to the Good Life pairs specific plays with particular life lessons. For example, Twelfth Night and acts of service, Julius Caesar and thinking for yourself, The Tempest and forgiveness, and Much Ado About Nothing and communication. Which pairing resonated with you the most? The least?

How do these life lessons translate to modern life?

The author emphasizes balancing appreciation for life’s joys and acceptance of life’s hardships. How do Shakespeare’s works illustrate this balance? Are there examples from your own life that reflect this idea?

Which character(s) in Shakespeare’s plays embody wisdom, compassion, or other aspects of a “good life”? What choices and actions reflect these traits?

All of the plays in Shakespeare’s Guide to the Good Life are comedies except for the tragedy of Julius Caesar. Why do you think the author made this choice? Do the life lessons show up differently in Shakespeare’s comedies versus his tragedies?

Each chapter includes a personal anecdote from the author. Could you relate to those stories?

Each chapter includes “Enactments” to allow the reader to apply the themes of compassion, hospitality, persistence, communication, thinking for yourself, service, friendship, communing with nature, imagination, and forgiveness in your own life. Have you tried any of the enactments? Which ones resonated with you? Why?

Were there moments in the book that changed how you think about difficult issues (like conflict, loss, or betrayal)? Which issues stood out to you?

How might Shakespeare’s (and the author’s) perspectives influence your response to future challenges?

The author presents Shakespeare not just as a playwright, but as a teacher of life lessons. Do you agree? Do you believe literature has a unique role in shaping how people perceive the nature of a “good life”?

Why might stories and characters influence us differently than non-fiction or self-help texts?

Do you feel the book deepened your appreciation of Shakespeare’s plays (even if you had read them before)?