The Art of Asking Liberating Questions

The Art of Asking Liberating Questions

on Jun 28, 2011 in Spirit | 6 comments

Photo by IceMan Photography/Flickr Creative Commons

Photo by IceMan Photography/Flickr Creative Commons

“A paradigm shift occurs when
a question is asked inside the current paradigm
that can only be answered from outside it.”
—Marilee Goldberg

Over the past few weeks, we’ve been exploring the territory of life-changing questions.

First, ten extraordinary people shared the most important question they’ve ever asked themselves. Then last week, Lisa Wilson gave us her beautiful story of the question that turned her life.

The right question at the right time is a key to unlock possibility in our life.

Over my years of training and practice as an anthropologist I’ve come to love questions. In fact, you could even call me a “questionologist.” I’ve got a passion for figuring how how to ask a great question, and one of my favorite books recently has been The Power of an Open Question by Elizabeth Mattis-Namgyel.

Questions really are a practice, in the sense that I wrote about a while ago when I defined practice like this:

An activity that you do on a regular basis (ideally each day)
that helps you to cultivate a sense of self-awareness, joy,
equanimity, resilience, and compassion for yourself and others.

So how do we work with questions as a practice? How do we ask the kinds of questions that have the potential to liberate our lives? Here are a few guidelines that I’ve found helpful:

1) Ask questions that will expand your mind and heart beyond their current limits and boundaries.
One way to do this is to watch for the assumptions that are embedded in the language of your questions. For example, you might ask yourself:

How can I get a job that will make me happy?”

Notice that there are two assumptions here: one is that you need to get a job, and the second is that the right kind of job will make you happy.

Now try looking at this from a different angle that bypasses those assumptions. You might ask,

“What would my life look like if I was completely involved in a project that I loved?”

This question moves you beyond both of those limitations and encourages you to think out of the box rather than repeating an old pattern.

2) As a general rule, don’t ask questions that can be answered with a “yes” or “no.”
Those questions almost always will cut you off from possibilities rather than create them. However, like any rule, there are times to break this one. The best exception I can think of is this question, which I often ask myself when I’m faced with a difficult choice:

“Am I making this decision from love or fear?”

In this case, the “yes” or “no” that reveals itself to me tells me everything.

3) Ask BIG questions.
Don’t stop with yourself. Let your questions lead you to a big vision of where we’re going as a collective society. Some examples:

“What would a healing and equitable society look like?”

“What would our planet look like if we could really recognize what a miracle it is to be alive and supported by the earth?”

Another way to do this is something called “backward engineering” – imagine the end point, the vision that you want to see come to fruition, and then work backwards with questions to identify what it would take to get to that point. Here’s an example that’s derived from the work of Joanna Macy:

Imagine that it is 100 years from now, and we as humans have found a way to get through the past century of environmental, social, and spiritual crisis. We have figured out how to live sustainably on the earth, how to be at peace with each other, how to resolve our conflicts without resorting to violence and war.

Sit down with each other and share the story of how we got here. What were the turning points that allowed this to happen? What gave you the strength to make it through the difficult times? Who was instrumental in this process?

4) Get comfortable asking questions that can’t be answered.
In the Zen Buddhist tradition, koans are questions which cannot be understood nor answered with our logical mind. Instead, we have to feel our way into them, live them, and watch how they unfold in our life. And then there is the marvelous quote from Rainer Maria Rilke:

Be patient toward all that is unsolved in your heart and try to love the questions themselves, like locked rooms and like books that are now written in a very foreign tongue. Do not now seek the answers, which cannot be given you because you would not be able to live them. And the point is, to live everything. Live the questions now. Perhaps you will then gradually, without noticing it, live along some distant day into the answer.


So those are some guidelines to work with if you feel called to this practice of questioning.

But if you just want a great list of questions to begin to sink your teeth into right now, here’s a collection to get you started. These come from the previous posts I’ve mentioned as well as questions that people on the LLP Facebook page have shared.

Pick one or more of these to work with, and watch the magic they work on you:

1. What am I waiting for?

2. Who would I be without that thought? (thanks to Byron Katie)

3. What would my life look like if I were liberated from fear?

4. What is the best possible outcome of this situation?

5. What is there for me to learn from this situation?

6. When is it better to be kind than to be right?

7. What is the most important thing in your life?

8. How does this serve me?

9. What am I doing here?

10. How can I best use my time and talents to contribute to rapid, positive, sustainable transformation in myself and in others I touch?

11. Is this who you want to continue to be?

12. How do I know you? What is our connection, our purpose for meeting or reconnecting? What is our soul history, our work, our future?

13. How am I feeling in this moment?

14. What can I give myself that will make me feel complete and make this experience complete?

15. How can I express my natural spirituality in everyday life?

16. Is this my work?

Please feel free to add to this list in the Comments section… what questions have you found liberating in your own life?


I’d love to stay in touch with you! When you sign up for my mailing list, you’ll receive my monthly newsletter with reflections on life and liberation, as well as my e-book, “9 Keys to a Liberated Life.”



  1. Loved the 16 questions. Took me to a form for a lot of the thoughts I’ve been having. Thank you.


    September 18, 2011

  2. Maia, great post!

    I constantly remind myself to question everything. But this is a practice that has been long since lost. It hasn’t been since I was 6 years old that I would in fact question the world around me. I can just picture some of the questions I would ask.

    “Why does money exist? Why do cows make milk? Why do we live in a house? Why do we park on the drive way and drive on the parkway?

    But then I grew up and accepted societies answers. So much so that I began to stop asking the questions.

    Thanks for the great and thought provoking reminder, to always challenge myself and the world with questions!


    Chris Barba

    June 30, 2011

  3. How about this one: “What liberating question can I ask now?”

    I just knew there was a reason I was attracted to your site and added it to my feed. I love this post!

    I was introduced to this idea (altho it was called “useful” questions) when I learned Matrix Energetics about 5 years ago. Powerful. I’ve been meaning to write a post about it myself but now I don’t have to — you’ve done such a good job. 😉

    One other thing I like to do is live in the question. Ask a question, leave it on the back burner, and watch how the answers unfold. Very fun.

    Thanks for a great post!

  4. Maia – what great great questions! some hard, some not so hard, all worthwhile to sink your teeth into!!! Thank you – mahalo!!!

    • You’re welcome, June! Have fun with these juicy questions…

      Maia Duerr

      June 28, 2011


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