This past week one of my previous yoga teacher trainees asked a question/made a comment about going further in the pose, as he had found that he is often able to be in poses in a way that feels easeful and doesn’t take a lot of energy to maintain and is a relaxing experience, but is still feeling like it’s moving further.
In addressing his question/comment, I think it is first important to define “going further” in a pose.  Initially and for a while, going further or deeper in a pose will look exactly as we would expect, as we move “forward” in the suggested direction of movement.   If we follow the direction of movement in the poses, we may find the “logical conclusion” of it for our body, when we reach a point of bony compression where further physical movement in that direction is no longer possible.  In that place, our body may look like we or our teacher expects, and it very well may not.  Some of our bodies may even end up looking like the pictures in the yoga magazines or on the inspiring and ridiculous 908 Yoga Poses poster in the restroom at Loving Kindness.  It is important to remember, over and over, that that is not the real point of yoga.
The real point of the physical practice, in my opinion, is to start the movement of Consciousness inward.   Most of our waking life is spent with our awareness focused outward.  From the yogic teachings and my experience and the experience of many others, True Happiness that we all seek is not to be found “out there” but is actually something that naturally arises as the closer we get to the Calm, Loving Center Inside.
The physical practice can also help us become aware of lost, scared, alone, traumatized parts of ourselves, and then in meeting those places with loving awareness, we can heal and integrate those parts, thus freeing the energy that had been unconsciously used to keep them hidden.  If we keep these ideas in mind, or remember it from time to time, then our physical practice can remain a more joyous experience, and we are less likely to get caught (for too long) in being driven by the outward form.
If we practice yoga long enough, though, we will inevitably experience times when “going deeper” in a pose would look from the outside like “backing off” especially if we have approached our practice from the “pusher” perspective.  Even if we weren’t a pusher when we began our practice, over time our sensitivity does get stronger, so that we will find that we have to “go back” to face and deal with the tensions that were so unconscious and habitual that we were not initially able to even be aware of them.  It doesn’t mean they aren’t there if we can’t perceive them, but to arrive more and more in a place that is easeful, comfortable, powerful and strong, we will have to do this “preliminary” work “later.”
So though moving further/deeper in the pose may at times follow a path that we expect or could predict, in the Big Picture, that is not the case.  The Path (of the pose, or, as we all know, of Life) is not predictable, direct or straight, so let’s not stress ourselves thinking that it is!
And one more note on moving “further/deeper” in the pose that is only appropriate for people to read/hear who are older than 40 (or more):  Sometimes maintenance is progress.  Remembering the “sometimes” in that sentence is important.
Progress in a pose is a difficult thing to measure from the outside, but with practice, assessed over time measured in years not necessarily day-to-day, we should be noticing that our awareness is more and more able to stay within, that the feeling-tone of the poses moves more toward comfort and ease and steadiness (sometimes with age, balancing is a notable exception to this), and that we are able to feel more and more relaxed in the pose, even in a state of intense activity.  If we are sensitive to it, we will also feel that the prana/energy is doing more and more of the “work” in the pose while we remain relaxedly aware and engaged.  The results of this “deepening” will be moving us toward deeper happiness, even a smile blossoming on our face for no apparent reason, arising from within the Heart.  We will also find ourselves being more patient, grounded, loving, kind, and willing to be of service in the world.  In the end, everyone benefits from our “personal” work on the mat.

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