Deep Questioning


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by Dr. Jennifer Howard –

How do you feel when you don’t know the answer to a question?


You might be thinking, well that depends on the question. Yet, many people feel anxious when they don’t have answers. As children some of us were told that it’s not ok to question things, or that someone who acts like they “know” is the real authority so asking questions might imply that you are less than others.

I like to look at questions and questioning in a different way, in a deeper way. Diving deeply into questions can take us to our heart and our true nature. 

Questions are the vital creative drive to knowing truth.

First of all, by simply asking a question we are admitting that we don’t know something. This can be a healing in and of itself. For some of us, it’s challenging to divulge that we aren’t sure about something, while others of us find it hard to acknowledge that we do know the answer. These differences depend on our history.

It is helpful to know how to ask these deeper questions. Learning how to ask questions in an open-ended, multi-dimensional way can lead to a deeply embodied unfoldment of reality, meaning we could have a new insight about something in a way we didn’t know was possible. 

This emerging unfoldment of knowledge leads us, again, to not knowing and more inquiry. Questioning in this way is not only about an answer, it’s about a way of living that allows for growth and fulfillment.


While the act of questioning implies not knowing something, it also implies knowing your limits. Acknowledging the fact that there are things you do not know shines a light on what you do know. It embodies authenticity through the ability to see yourself and the reality that you are living in more clearly.

A moment comes and a question arises; this query comes from a longing to understand something more fully. Following this longing or quest is an opening to your passion and your creativity.

With all these juices flowing, it’s important to be able to calm the urgency around finding the answer, so that you can sink into the fertile openness of the question. By letting yourself sink into all the layers of this question, you allow the mysteries of the universe to be revealed.

It’s interesting to think about the way that “not knowing” points to the possibility of actually gaining more knowledge. This leads us to further discovery, experience and expansion.

Allowing the question to just be for a while can take us on a journey deep within us to the ground of our being, from which both knowing and not knowing arise. Being seated in this larger context can sometimes stir up uncomfortable feelings. Tolerating these feelings is how we can enjoy the fruit of this human journey. For knowing and not knowing can be present at the same time and when embraced, can lead us to more wholeness, freedom, play and creativity.

When a question arises, these seven keys to deep questioning can help you develop your experience of both the question and the answer. 

Each of these keys comes with questions of their own but this is not a test. There are no right answers. This is an opportunity to explore the context that surrounds, inhabits and gave birth to your question. Here is an invitation to bring your mind, body, heart and soul together for a multi-dimensional experience of your question. This is a chance for you to dive deeply into yourself and discover the layers of meaning surrounding both your question and your answer, leading you to more fulfillment and happiness.

Keys to Deep Questioning

1. Where is this question coming from? Is your question coming from a particular belief, fear, need, or assumption? Why are you asking the question, now? What prompted it?

2. What part of you is speaking? Is this question being asked by the mature adult self within you, a child self or some other part? Or is it coming from a part of you that has previously been silent because it’s been shamed, shunned, put away, or unexplored? What allowed you to let this part of you speak now?

3. What is the longing behind the question? Are you trying to find the “right answer” to please, or prove something, to someone else? Are you trying to appease the discomfort of not knowing? What is the longing that gave birth to this question, and what is it connected to inside of you? Where do you feel this longing in your body? Does it have a particular shape or color? What happens when you breathe into it?

4. What are the layers of the question that want to be seen? As you sit a moment with your question, are you aware of any previous thoughts, feelings, or questions that may have inspired this question? Are you aware of any questions that would naturally follow it? If you received the answer you wanted, what feelings would arise in you as a consequence? Would any new questions be sparked by this? What is the essence of the question you’re asking?

5. What assumptions have you made in this question? As you ask your question, look to see if you’re making any assumptions about yourself, about others, about what you’re questioning, or about reality. If you’re making any assumptions, what is the history behind them?

6. Is there any separation between the question and you the questioner? Like a Zen Koan, this question lives beyond the logical mind. Allow yourself to simply hold your question in mind and notice what you experience as you hold it. Can you feel your way into the gap between the question and the answer? As you do that, can you feel your way into the gap between the question and you as the asker of the question?

7. Breathe a moment of kindness for yourself as you ask these questions. Take a slow deep breath in and out, allowing kindness to permeate your body. Be gentle with yourself on this journey.

Allow yourself to open to your questions, to your heart, to your true nature, to life itself, to further knowledge, to further truth and to more compassion. 

This act of questioning can lead us into our deepest satisfaction and to ever-present wholeness.


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