May 2014

Twenty Questions Times Five


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In the February issue of Blue River Monthly, there’s a reference in "The Importance of Your Questions" to an exercise involving 100 questions that you’d like to have answered. It was promised in that article that the value of such an exercise would be discussed in a future article. This month we’ll explore the process of asking yourself 100 questions and see how it can be a useful tool.

This exercise comes from the book, How to Think like Leonardo da Vinci, by Michael J. Gelb. In this intriguing book, Gelb considers seven principles that were important to da Vinci. He also supplies exercises for the reader that are related to those principles.

Asking yourself 100 questions

Much of the time, I simply read about exercises that are described in books and don’t feel an interest in trying them. But the first exercise in How to Think like Leonardo da Vinci seemed especially compelling. The exercise is titled “A Hundred Questions” and it appears in a chapter that is all about curiosity.

Gelb suggests that you “make a list of a hundred questions that are important to you.” He also suggests that you complete the list all in one sitting and that you don’t worry about spelling or grammar. If you’re wondering why he recommends a total of 100 questions, he writes that, “in the latter part of the second half of the list you are likely to discover unexpected but profound material.”

Once you have your list of 100 questions, Gelb recommends selecting your “Top Ten Questions” from the list and ranking them in order of importance. Creating a “Top Ten” list gives you a reason to go through your list of 100 questions and assess their importance. And the resulting list of “Top Ten Questions” can be beneficial in and of itself. It might help you target questions that you’d like to concentrate on sometime soon. Gelb presents some examples from lists that people have constructed of “Top Ten Questions,” such as “What is my greatest talent?” and “How can I best be of service to others?”

Giving it a try

I did both of these exercises—writing down a list of 100 questions and then picking out my “Top Ten”—back in November 2010. Looking back on my list of 100 questions, I notice that about half of them have either been answered or are no longer relevant due to changing circumstances. The first four questions on that list are related to searching for a new home, such as “Where should we move to?” Those questions were answered when my husband and I moved to Charlottesville in 2011. Some of the questions in the second half of the list are more profound, such as “How does one come to terms with being a finite part of something infinite?” I’m still working on the answer to that one.

When you look over your list of 100 questions, it’s interesting to see what themes or patterns might emerge. As Gelb notes, some questions may appear on your list repeatedly, in different wording; such questions may help you to detect some patterns.

Your current concerns, fears, hopes, worries and dreams can all affect the types of questions that you put on your initial list. When you go over your “Top Ten” list, you might realize that you’ve been wondering about some of those questions for months or years—and it might occur to you that you’d like to focus on one or more of them in the near future. The first question on my “Top Ten” list is “What are my most important values?” That was a question that I chose to focus on, and it was very worthwhile to concentrate on that and to put the answer down on paper.

Before you start your own list

By this point, you may be interested in working on your own list of 100 questions. Before you start, here are a few more observations. Although Gelb discusses writing the list of 100 questions in one session, you may want to take a break partway through. My hand was quite sore after writing 100 questions without stopping! In addition, you could type your list into an electronic document instead of using a pen or pencil, but writing it out on paper lends more of a fluidity to the process.

Coincidentally, an article titled “20 Questions Every Woman Should Ask Herself” appeared in the April 2014 issue of O Magazine. It’s valuable to see what questions are included in that article and how others answer those questions. But it seems more powerful to come up with your own list of 100 questions, as your own list will pertain to your particular priorities.

Your list of 100 questions can be something that you periodically refer back to over the course of years. During the three and a half years that have passed since I wrote my list, I have found myself on occasion reviewing it to see what I might want to focus on next and what questions I’ve answered lately. I can imagine writing a brand-new list of “twenty questions times five” in the next couple of years, but as of now my original list is still going strong as a useful tool.

-- By Mary Jablonski

See features from the May 2014 issue

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