The Fun Doesn’t Start Until Something Goes Wrong
These questions are meant to start conversations, arguments, confessions, and possibly the planning of ill-advised trips.
Start Here
- Which story would you tell a friend about first—and why that one?
- Which chapter made you laugh hardest? Which one stayed with you longest?
- Which trip in the book would you most like to join? Which would you avoid at all costs?
- Did the book make you want to travel more—or travel differently?
- The title offers a philosophy of travel. When is that philosophy liberating, and when might it become reckless?
When Things Go Wrong
- In “The Boat Was Gone,” what is more frightening: the danger itself or the realization that nobody noticed?
- Does travel reveal who we already are, or does it create a different version of us?
- In “The Gift of Intuition,” the body understands danger before the mind does. How can we distinguish intuition from fear, bias, or imagination?
- “Stairway to Nowhere” reveals Dave’s personal weakness. What reliably short-circuits your own good judgment?
- In “Buffalo Camp,” a ruined plan produces an unforgettable night. Does inconvenience become a gift only after we know everything worked out?
Other People, Other Worlds
- Is “trail magic” really magic, or simply what happens when people decide to look after one another?
- What does a traveler owe the people whose hardship becomes part of a memorable story?
- In “A Nation in Need of Self-Care,” does travel provide special insight into neglected communities, or can a visitor judge a place too quickly?
- “The Private Life of Places” argues that drinking with locals reveals a destination’s true character. Does alcohol uncover truth, or merely create a different performance?
- Which person in the book taught Dave the most without intending to teach him anything?
- The book repeatedly challenges cultural stereotypes. Which assumption was most effectively overturned?
- Is it possible to love a place while also seeing its cruelty, prejudice, or dysfunction clearly?
Looking Inward
- Several stories show Dave discovering something uncomfortable about himself. Which act of self-examination (if any) felt most honest?
- In the Japan chapters, does he judge his younger self fairly—or too harshly?
- Dave often talks about gaining some measure of humility through travel. Is humility one of travel’s natural products, or does the traveler have to actively choose it?
- In “A Modest Man on an Immodest Coast,” disgust becomes a clue to hidden prejudice. What emotions are most useful in exposing our blind spots?
- Are strange experiences less meaningful when they have a rational explanation, as in “The Dude Rancher”?
- The book suggests that some lessons take decades to ripen. Which story seems to have changed most in meaning between the event and the telling?
Change, Progress, and Loss
- Read together, “Private Property” and “A Grand Transformation” offer opposite views of change. When does development represent progress, and when does it become loss?
- Who gets to decide whether a destination has improved: residents, visitors, businesses, governments, or future generations?
- Can nostalgia help us protect places, or does it prevent us from accepting necessary change?
- In “Rapists and Thieves,” where does responsibility for cartel violence ultimately lie? Did the restaurant scene change how you thought about that question?
Friendship, Mortality, and Gratitude
- Chuck’s great gift was noticing what called to someone–and helping that person pursue it. Who has done that for you?
- What does the instruction “When someone you love tells you what calls to them, pay attention. Help them go” ask of a friendship?
- “Chuck’s Last Meal” and “I ❤️ Boston” celebrate systems and workers people often complain about. Did either story change how you see these systems and people?
- Does gratitude require a close call, or can we learn to feel it without first nearly losing something?
- If you knew your time was shorter than expected, what trip—or conversation—would move to the top of your list?
The View From the End
- “The Umwelt of Salmon and Bears” asks us to imagine realities beyond human perception. Which animal’s senses would you borrow for one day, and where would you go?
- In Patagonia, violent winds make the natural world feel almost intentional. Have you ever visited a place that seemed to possess a personality?
- Does “When Nothing Goes Wrong” contradict the book’s title—or complete its meaning?
- The book argues that travel changes the ground beneath us and helps us see differently. Are these lessons unique to travel, or could we learn them without leaving home?
Finish With a Little Trouble
- Which character would you rather have a conversation with and why: Chuck, Diego the Raiders-loving narco, Scott the scuba guide, or the ghost at the Dude Rancher?
- Create a warning label for your own travel style.
- Tell the group about a trip where something went wrong and later became the best part of the story.
