A Dean’s five questions

at the school which, in spite of the professor’s limited fame, found audiences across the globe. The 25-minute speech, about what Mr Ryan called “the beauty and power of good questions”, drew applause from many quarters, including an editor at Harper Collins who asked Mr Ryan to expand his ideas into a book.

And therein lies the rub. A graduation speech, no matter how poignant, works primarily as a speech. A collection of words delivered in the right register and to the right amounts of applause can rise above its, no doubt heartening, message to become an attractive cultural product. On the page, however, the same words can end up sounding preachy, like a watered-down version of a self-help book.

To those on the cusp of a new life, as any freshly-minted graduate is, guidance on asking the right questions indeed makes for good advice. Mr Ryan jokes that a lot of people, not least the parents who have pumped bucketloads of money into their education, would now expect the graduates to have all the answers. And so he sets out on his mission to help his wards—and the wider world—learn how to frame the right question.

In his speech, Mr Ryan spoke about the five questions that all of us must focus on to lead more fulfilling lives. His list: “Wait, what?”; “I wonder…”; “Couldn’t we at least…”; “How can I help?”; and “What truly matters…” It’s a nice enough compilation and moves progressively from better understanding our material needs to accounting for how we can come together with others to create deeply connected communities.

Mr Ryan expands the scope in the book by citing an array of personal examples, for instance, the time when he and his wife Katie were certain that they had prepared for every eventuality for her delivery, until of course, the real world intervened and they were left at the mercy of assorted doctors. Following a complication, the doctor said he was going to press Katie’s stomach and squeeze the baby out, “like you might squeeze a pit out of an olive.” The scene, together with the indelicate analogy, prompted Mr Ryan to utter: “Wait, what?”

Wait, what?, he explains, allows us to both grasp the newness of a situation and prepare ourselves to handle the additional information. This may seem intuitive and hardly worthy of writing a book about, which explains why the book can sometimes seem overwritten, even redundant. But Mr Ryan’s willingness to explore deeper questions about his life and identity lends gravitas to his project.

He begins the “I wonder…” chapter with expected spiels about how curiosity is the fount of great inventions and discoveries. But it quickly moves into different territory, as Mr Ryan explains why he never searched for his biological parents until he was 46, when a friend got him to do it. This unleashed a chain of events that led Mr Ryan to meet his biological mother who lived not far from him in New Jersey.

Linking “I wonder…” to a heartbreaking story of love and loss may be a stretch—indeed, the fact that Mr Ryan never looked until late in his life militates against “I wonder…”—but it is hard to quibble about such minor details. In “How can I Help?”, Mr Ryan narrates a similarly moving story of an asylum seeker to the US whom he helped find a house. That set in motion a virtuous cycle that led to the man getting a job and ultimately receiving asylum. Mr Ryan was the best man at his wedding.

The real takeaway from this book, then, is not necessarily the importance of asking the right questions but of keeping an open mind and empathising with others. To be sure, questions are just one way to reach out, and the right intentions can be communicated via very many other means. It is also true that Mr Ryan’s stories work because they end a certain way—happy anecdotes with an inspirational lesson rather than cautionary tales about the dangers of too much openness.

But that, as I said, would be quibbling. Mr Ryan is a professor in the Harvard ecosystem that churns out political leaders, financiers, lawyers and consultants by the dozen, a list of professions rarely mentioned in the same breadth as empathy. If his speech, and now this book, can get some of his students to think about matters less pecuniary, his purpose would have been served. And Life’s Other Essential Questions James E Ryan Harper One 138 pages; ~499