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Back to What Should I Do With My Life?

A Reading Group Guide
(Prepared by Random House editors in consultation with the author)

For Book Clubs and Others Seeking Further Provocation (A User's Guide, if you will)

Now that you've read What Should I Do With My Life, we highly recommend discussing it with your friends, family, or book group. We suggest the following questions as fodder for those discussions.

Artistic Choices
Strategies & Macro Influences
Finding Your Story


1. Po chose to weave in fragments of his life when his memories were triggered by the stories of others. How did this enhance or detract from your experience of reading the book? Did his doing so encourage you to think about your own memories, or did it get in the way?

2. Journalists are supposed to be impartial. They’re not supposed to overtly care for the people they write about. In rejecting that method, Po seemed to be suggesting that caring for others is necessary for a meaningful life. Do you agree? What would Po have gained or missed if he had adopted a journalist’s customary detachment?

3. Most of the stories have positive outcomes, but the subjects have to endure a painful period to get there, and they’re still tinged with regret and uncertainty afterwards. Did you find the overall picture rosy or sad? Did you expect otherwise?

4. Po chose to include several stories of people who are still struggling, or who have found only part of their solution. He also chose ordinary people, rather than famous ones. Why do you think he made these choices? How does it influence the overall tone of the book?

5. Was part of your enjoyment the fantasy of being welcomed into the intimate lives of strangers? Was part of your enjoyment the sense that there’s someone out there who would be willing to listen to your life story? How important to your enjoyment was getting concrete wisdom from the stories?

6. Po recorded the stories of over 900 people. That suggests he wanted to be encompassing and representative of everyone, but he freely admits that his research was biased heavily towards the kind of person he used to be (and the kind of people he used to write about). Does this influence the legitimacy of his conclusions? In what ways has your perspective also been limited by where you come from?

7. Po categorized the stories in a way that highlighted the psychological issues we have in common. He rejected methods of categorization that would have sorted people by profession, age, or class. Thus, the story of an electrician is followed by a political appointee, and the story of a mother is followed by a trucker, etc. What is the author trying to say about the way people usually identify themselves?

8. Po clearly chose not to write a How-To guidebook. But he seems torn between two ambitions – his desire to be a serious chronicler, which dictated recording the stories straight, and his desire to help readers, which lead him to distill helpful insights. When did he cross over too far, in either direction? Do you work in a field where wanting to help others means you are taken less seriously?


9. Did you think any of these people should have stayed put, rather than leave their old life behind? Whose choices did you question or criticize? For instance, did you question Carl Kurlander’s decision to write Louie Anderson’s autobiography, rather than his own? Did you accept or reject Mark Kraschel’s appreciation for Muslim culture? Did you respect Katt Clark’s decision to set aside her Olympic dreams for her daughter a second time?

10. Many of these people left professions where they would have made a lot of money, and in some cases did. What message do you extract from this – that it’s necessary to resist the temptation of money, and the sooner the better, to avoid being locked in by golden handcuffs? Or does their example suggest that it’s possible to follow in their path, aiming for money now and postponing your calling until later?

11. Katherine James, Warren Brown, Debbie Brient and Jennifer Scott were among the many who believed they were being steered towards the right decision. Do you believe in destiny, or a guiding hand? If so, what should one do when the universe seems to be making it very, very hard to succeed? – is that a sign you’re going in the wrong direction?

12. Po concludes that a calling isn’t something you know, in the absence of experience, it’s something you grow into. Many of the people in this book weren’t able to figure out where they really belonged until the second half of their life. How should this influence the way we counsel students, who want to find their answer now, not later?

13. Every industry has a culture. And every culture is driven by a value system. Po urges us to recognize how these value systems have shaped us, for better or worse. What is the culture of the industry in which you work? What does it value in a person, and what doesn’t it value?

14. How have you and your spouse (or partner) helped each other in your pursuit? How have you hindered each other? Have you chosen partners because they helped you succeed? Po confesses that he used the support of his first wife like a crutch – that he didn’t take sole responsibility for his own situation. Do you agree that generous support can lead to neglect of responsibilities?

15. Roughly half the people in the book are parents. The other half aren’t – at least yet (either because they’ve delayed doing so, or they haven’t found their partner). Did you read their story differently if they had children? Did you relate to them differently?

16. When you’ve had to counsel friends or family who are facing an agonizing decision, how have you balanced the need to be supportive against the need to be realistic? To what extent is your counseling strategy reflective of your own successes and failures?

17. Po says that we’re all struggling to transcend the way our class defines us. He seems to be saying that the inequity between classes is a wound in our collective psyche. Do you think it’s that relevant – does it really affect our individual enjoyment of life?

18. At LSU, Mike Blandino’s Buddhism taught him to find his answers in his state of being, not doing. In Indiana, Barry Brown was influenced by the sermons of an old-time Calvinist. Mike Jenzeh was guided by Isaiah 58 of the Old Testament. At the Unity Church in Bandon, John Butler taught that what we consider our strengths are limiting beliefs compensating for our biases and weaknesses. At St. Agatha’s in Los Angeles, Father Joe preached that helping others is the way to serve God. How does your religion affect your pursuit of this question? Do you agree with your church’s teaching?


19. What have you been called to, over the course of your life? Have you listened to those calls? Which have you acted upon, and which have you chosen not to?

20. Write a one-page memory of a time during your childhood or teen years that you managed to succeed at something that you were afraid of trying or convinced you would fail at.

21. In the first section, Po portrays various ways of arriving at "a sense of rightness," such as analyzing your skills, or watching for synchronicity, or wanting to help others who have suffered similar tragedies and losses. Po also says we’re as likely to simply stumble into a place that feels right as arrive there by reasoned planning. Which of these ways have you used when telling your story to others? Could you tell your story using the other methods?

22. Po concludes that it’s in hard times that we’re forced to overcome the fears and doubts that normally give us pause. To what extent have the changes in your life been self-selected, during good times, or been forced upon you, during hard ones? When you’ve suffered hardship, has it altered what you consider important? Has hardship changed your life, or have you fought to get back to "normal"?

23. Po warns against editing out important pieces of our story in order to make our story more presentable to others. "Embrace your luck, pain and ghosts," he suggests in one chapter; in another he writes, "look backward even more than forward, and chase away preconceptions of what our story is supposed to sound like." He contrasts the Resume Version with the Work-In-Progress Version. How do you describe yourself in a public situation? How do you do so differently in a private situation? What failures do you rarely bring up? Do you agree that we should be more revealing of our "real story" in public situations?

24. In the chapter "The Brain Candy Generation," Po says the true search is for what you believe in – what kind of world you want to live in. In what ways are you making the world a better place – even if it’s just one quality interaction at a time?

25. Po tells Tom Scott that happiness is too easy a test; rather, we should ask what will be fulfilling. Leela de Souza found that fulfillment when she stopped asking what would make her happy, and instead asked "to what could she devote her life?" Mike Jenzeh’s life improved when he gave up that it was all about himself. Yet these stories are balanced by the likes of Warren Brown, who stopped suppressing what made him happy, and Kurt Slauson, who had been denying himself permission to enjoy his life. Have the most fulfilling periods of your life also been happy ones? Is happiness essential?

26. Bart Handford tells Po the parable of the three bricklayers building a cathedral, suggesting that even menial work can be meaningful if it’s contributing to something you believe in. Have your most meaningful accomplishments required a lot of menial work?

27. Po suggests that temptations can come in many forms: in the form of money, respect, love, and convenience. Write a one page memory about a time in your adult life that you resisted one of these temptations.

28. In the chapter "The Ungrateful Soldier," Po recounts C.S. Lewis’s assertion that belonging to an Inner Ring is a powerful, wayward desire. Po asks Tim Bratcher who’s sitting at that table – who’s in his Inner Ring. Are there ways you’ve used status as a surrogate for individual expression? What elusive ring do you long to belong to? Are there people in your life (or in your past) that you don’t respect, yet are still trying to prove wrong?

29. Both Stephen Lyons and Chi Tschang tell Po that if you can develop into a person of good character, your chances of succeeding in life improve dramatically. What do they mean by "character"? What’s an example from your own life of good or bad character?