Inspired by and with excerpts from Tricycle, "Practicing Questioning", by Narayan Helen Liebenson.

Check in question: Who am I?

The beginning foundation—even if it doesn’t sound like a foundation—is actually the willingness not to know, or at least the willingness not to be certain. We start to hold things a little more loosely. When we start to hold things less tightly, the veils through which we tend to perceive things just naturally start to settle. If it doesn’t start with some visceral sense of not knowing, we’re not going to get very far.
- Adyashanti

Q: What are your veils?

The I-Thought

...the individual self is nothing more than a thought or an idea. He said that this thought, which he called 'I'-thought, originates from a place called the Heart-centre, which he located [in the] chest...From there the 'I'-thought rises up to the brain and identifies itself with the body: 'I am this body.' It then creates the illusion that there is a mind or an individual self which inhabits the body and which controls all its thoughts and actions. The 'I'-thought accomplishes this by identifying itself with all the thoughts and perceptions that go on in the body.
- David Godman on Ramana Maharshi

Q: How do you respond to self as an idea?

One more contemporary way of thinking about the "I-thought" is the Mind System suggested by John Yates.

• There are sensory sub-minds for sight, smell, touch, sound, etc. We're not conscious of these at work. E.g., visual mind sends "black and red bird shape". Imagine a screen onto which this is projected. There is only seeing at this point.
• Each sensory sub-mind passes its seeing, smelling, touching information along to the discriminating mind, which apply thought and perhaps emotion, e.g., recognition "red-winged blackbird" and feeling "pleasant colours!". There is only recognition and feeling at this point.
• At this point, seeing, recognizing, and feeling are separate events simply happening.
• Then the narrating mind, the storytelling mind, weaves them together as connected episodes: "I saw it, I recognized it, I enjoyed it."
• The "I" is born!

If you keep your attention on the source from where all thoughts arise, the mind will subside there at the source and reality will shine forth.
- Sri Ramana Maharshi, 1879–1950

Practicing

The practice of wise questioning isn't conceptual or analytical.

In this practice, doubt is totally OK—we’re encouraged to test the teachings out so that they become our own. But questions like, “Why am I here?”, “What is the meaning of life?”, “When can I get what I want, or get rid of what I don’t want?”, “Why am I so deluded?”, or “Why are others so deluded?” tend to take us nowhere. I’ve found that they cause us to circle around and around and do not reveal a way out. The deep inquiry I’m talking about doesn’t mean constantly questioning oneself, obsessing, or running after thoughts.
- Liebenson

Affectionate curiosity

What about not knowing?

We encourage ourselves to rest in what is sometimes called “don’t know mind,” which means open to whatever may emerge.
- Liebenson

Or as Adyashanti wrote:

In our culture, not knowing is not highly valued, but spiritually, it’s one of the highest values there is. When we open ourselves to the mystery of being, that’s always the doorway—whether it’s the mystery of who you are, the mystery of life, the mystery of God, or the mystery of somebody who’s had a kind of spiritual opening and they’re wondering how they can embody it and live from it.

Settle, Ask, Listen

For each question, first settle, then silently ask, then listen deeply - not for concepts or dictionary definitions but for subtle echoes, peripheral slips, invitations, hints...

• What is my mind aware of right now?

• Is there any moment better than this one?

• Where is kindness?