I read "Wait, What?" by James E. Ryan as part of my research on the "second act." James E. Ryan is the dean of Harvard University's Graduate School of Education. The book originated as a graduation speech Ryan delivered for Harvard School of Education students. I listened to the speech first and found it to contain some good advice and information I might use in the class I'm thinking about leading, so I ordered the book. Unfortunately, much of the book is word-for-word from the speech. Ryan does, however, add anecdotes from his own life and examples from current events to support his ideas. I'm not sure that I needed to read the book after listening to the speech. Nevertheless, I will use the book as a resource for class participants.
Ryan posits that the ability to ask good questions leads to better being able to ANSWER life's important questions and, thus, lead a better life. Those questions are: "Wait, what?," "I wonder...?," "Couldn't we at least..?," "How can I help?," "What truly matters?," and the BONUS question "And did you get what you wanted from this life, even so?" (He says the answer will likely be "YES" if you have repeatedly asked these questions throughout your life.)
"Wait, What?" by James R. Ryan might be a nice book to give as a gift for those milestone occasions, as it is a fast, easy, thought-provoking read. Otherwise, I'd check this one out from the library, or listen to the speech online, rather than investing the $20 to purchase it.