Asking the Beautiful Questions

As a teacher, I have two options. I can try to teach the answer or I can try to teach the question. All too often, the “answer” is burdened by my own judgment, opinion, beliefs and experience. Teaching the answer can be limiting because everyone’s experience is different. But when I teach the question, infinite possibilities are unleashed. We open to imagination and creativity.

Poet and author David Whyte writes, “What would it be like to see teaching as the ability to cultivate the imagination? To [help students] create the biggest context they can for whatever they are being taught. . . if we are able to construct a question that is beautiful, it will stay with them for the rest of their life.” Deep and open-ended questions lead us to connect with that which gives us meaning and purpose. Whyte has compiled a list of 10 Questions That Have No Right To Go Away. They include:

What can I be wholehearted about? Am I harvesting this year’s season of my life? Can I be quiet, even inside? Am I too inflexible in my relationship to time? How can I drink from the deep well of things as they are? Can I live a courageous life?

These questions don’t demand answers but instead reflection. And lived experience. The practice of mindfulness invites us to welcome these questions and explore. I invite you to try some of these questions on for size at our workshop, Asking The Beautiful Questions, this Saturday, December 2. Register today or read below for more details.



We all know that questions can be empowering or restricting depending on how they are framed. My teacher Jonathan Foust offers four empowering questions:


What are you most excited about in your life right now?

What are you most proud of in your life right now?

What are you most grateful for in your life right now?

What are you most committed to in your life right now?

Notice how these questions challenge you to shift out of the mindset of problem-solving, thinking, comparing and judging that characterizes most of our everyday experience. We might find responding to such questions difficult because they remind us of what’s not quite right yet. But it also opens the possibility for growth, meaning and understanding. In practice, one needn’t search for the answers but instead allow them to arise. Some of the responses may be strange and unexpected but also illuminating.

A perfect example of how empowering questions open our minds and hearts comes from StoryCorps, whose mission is “to preserve and share humanity’s stories in order to build connections between people and create a more just and compassionate world.” You may have heard these stories on National Public Radio. Check out this list of wonderful questions for just about any situation that are sure to get right to the heart of the matter.

Here are just a few of the qualities that inquiry and questions can generate:reframe-nlp-frame

  • Reframing – Questions allow us look at our experience from a different angle. Approaching an issue with a different kind of question shifts our perception and our attitude.
  • Softening – They can bring a compassion, an appreciation and even a forgiveness for difficulty, confusion and uncertainty we face.
  • Opening – How many ways could I describe the situation? What are the new ways?
  • Clarifying – What is really happening right now? Can I be with it? What is important to me? What will I do next?
  • Identifying habit patterns that aren’t supportive of wholehearted living, happiness and resilience. We begin to recognize our reactivity and how it may harm us.
  • Connection with our passion, our values, and our heart to create purpose and meaning.

At its heart, the practice of mindfulness asks two questions, “What is happening?” and “Can I be with it?” These two questions represent the two wings of the metaphorical bird. Wisdom to see clearly with awareness and compassion to non-judgmentally be with our experience. In a sense, these are the questions that characterize the experience of mindfulness. As we practice mindfulness, we step out of the story we’ve created in our minds and into the genuine experience of being alive, with its joy, its sorrow, its uncertainty, its faith.

I welcome you to explore questions further by listening to Inquiry as Mindfulness Practice, via iTunes or Stitcher. This episode includes a meditative inquiry practice called The Five Problem Solving Questions which I think you’ll enjoy experimenting with.

If you live in the Philadelphia area, please join me on Saturday, December 2 for Asking The Beautiful Questions from 10am-12pm at the Tredyffrin Public Library in Strafford, PA.  You can learn more by visiting or You also might enjoy a visit to or to learn more about the tools of meditative inquiry.

Sometimes by David Whyte

David Whyte

if you move carefully
through the forest

like the ones
in the old stories

who could cross
a shimmering bed of dry leaves
without a sound, 

you come
to a place
whose only task

is to trouble you
with tiny
but frightening requests

conceived out of nowhere
but in this place
beginning to lead everywhere.

Requests to stop what
you are doing right now,

to stop what you
are becoming
while you do it,

that can make
or unmake
a life,

that have patiently
waited for you,

that have no right
to go away.

Portions of this post were originally published on the Your Mindful Coach Blog in December 2016.


2 thoughts on “Asking the Beautiful Questions

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