What I suggest is that instead of trying to practice all of these three conditions at the same time, you choose one to influence your meditation sittings for the time being, and then wait and see how the other two come into play.

The one to begin with for those new to meditation is gentleness. For those with an established meditation practice, begin with permission (but still read the section on gentleness). Those who tend to think a great deal during meditation (and outside of it) may want to begin with interest.

Before you begin meditating, in order for this to have a reasonable chance of working for you, you need to commit yourself to meditating in this way for at least one week (5 to 7 meditation sittings).

Gentleness

“Be gentle to yourself,” I often say at the beginning of a workshop or retreat. Then I usually say something like, “In America, most of us are self-critical. We want to do things well. But we don’t treat ourselves all that well in the process.”

Gentleness in meditation is about how you treat yourself. Many meditators start their meditation sittings by diving right into doing the instructions they have been taught. They don’t just bring their attention to the breath, a mantra, or visualization, but rather force it. Behind that force is aggression, pressure, driven-ness, or just plain tension. And when things don’t go well, they tend to chastise themselves with thoughts of failure and self-doubt.

So, to start off a meditation sitting with gentleness is to not dive right into doing some kind of instruction or practice. Simply allow a transition to occur. What you were thinking about before the meditation sitting will naturally carry on into the beginning of the sitting. Many meditators start off a sitting by trying to stop all thoughts. Thoughts, when they arise, are then perceived as distractions. Here is where gentleness truly starts in meditation. These thoughts coming into your sitting are not distractions, for they are your thoughts, and most of the time outside of meditation, you are the one who owns them, acts on them, and produces more of them. They are to be welcomed into the meditation sitting just as you would welcome a friend, a relative, or even someone you may not particularly like into your home.

How to Begin a Meditation Sitting with Gentleness

A. Choose a comfortable posture to sit in, one that will not cause pain or create additional posture changes during the sitting. You may sit in a chair, have back support, or lie down on your back. Whatever posture you choose, make sure it is gentle to your body. If you have to move for some reason during the sitting, be aware of the pain, itch, or discomfort you are experiencing, and only then decide to move, moving slowly and deliberately. When you move slowly and deliberately during a meditation sitting, there is less likelihood that the movement will feel disruptive.

B. Choose a length of time for the meditation sitting that is easy to begin with. One hour is generally too long, while five minutes is definitely too short. Most people find twenty or thirty minute long meditation sittings to be just right. Use a gentle sounding alarm or glance at a watch or clock on occasion. If you become restless, anxious, or extremely bored before the end of the sitting, allow yourself to end the sitting early. And if you would like to continue to sit behind the time you set for yourself, make sure you have given yourself enough time between the end of the sitting and whatever you may need to do after the sitting.

C. Sit with your eyes closed, as that will enable a meditative process to form more readily (as well as bring the other senses more into awareness). You may then bring your attention to the front of your face, your hands resting on your legs or one on top of the other, or your legs and feet touching the cushion you are sitting on. But do not hold your attention there, and definitely do not cut off thoughts, feelings, and sounds to return to the awareness of your body. Just have a gentle preference for your body sitting as you allow your thoughts and feelings to be.

D. Allow your mind to transition from what you were doing and thinking about before the sitting. This transition may contain recent memories, dialogues you just had, work you were doing, plans that you were making, lists of things to do, feelings of resentment, hurt, and rage, as well as feelings of hope, longing, and love, to name but a few of the themes you may encounter at any given time. You may fear that the transition will not be a transition at all, but will consume you for the entire sitting. If you are gentle with it, with all that is going inside of you as you sit down to meditate, it is bound to change for better. But if you are impatient with it (your thoughts and feelings) and try to stop it or do something to make it go away, you may just end up being hard on yourself, prolonging the difficulty. Being gentle with it, if it doesn’t stop it, at least makes it less of a problem, less of a negative self-judgment.

Permission

You have permission to do the meditation practice of your choice, or, not do it. Practically all people who are introduced to meditation are given an instruction to follow, and they follow it. Few rebel against the instruction (or the teacher), believing that in order to get the right results from meditation they must follow a particular instruction. This creates an atmosphere of conformity when everybody is following the same instruction (or teacher), or an atmosphere of factionalism when students of different teachers meet in large groups.

Very few teachers truly accept all “wholesome” meditation practices as being of value. Even if they allow for people doing other practices than what they teach, these teachers will still hold their method as the right one, or the best one. It has taken me several years as a meditation teacher to work this problem through. I don’t teach a smorgasbord of meditation techniques, which is how several meditation teachers have resolved this issue without dealing with it. What I do instead is teach a way to explore the various meditation practices one has done (or is doing).

To explore one’s various meditation practices, one needs to do them. So students of mine have permission to do the practices they have done. Only this time they attempt to look at those practices and see some of the habits of mind they have developed by doing them. They also have permission not to do the practices they have done. They can do whatever is necessary for them. And they can rebel against my approach as much as they want.

Because what happens is that the students become independent. They are not dependent on me for the “right” instruction. Instead they form a relationship with me where we are both genuinely interested in what meditation is for them. I listen to people meditate their own way, not my way. I help them see what they are doing in meditation, and from that they see how skillful (or unskillful) they are at times.

The unfortunate, but necessary, consequences of independence are confusion, uncertainty, and doubt. When I hear a meditator speak of his confusion, I hear someone who is seriously applying himself to meditation and struggling to understand his experiences. When someone speaks of uncertainty, I hear surface certainties, convictions, and beliefs no longer having power over him. He is ready for true self-exploration. And when I hear someone doubt about ever becoming enlightened through meditation, I recognize someone who is beginning to see himself as he is and how far enlightenment appears to be when someone is honest about himself.

How to Begin Meditating with Permission

A. You have permission to meditate as you have been. If you choose not to meditate in your accustomed way at any point in the meditation sitting, you can use A through D of the previous section on gentleness.

B. After the sitting is over take a few moments to recollect the meditation sitting. In your recollection bring your attention to how you applied the instructions and what your “honest” experience of doing that practice was.

Interest

Interest, at the beginning, looks the least like itself than the other two conditions for exploration. At this stage it would be better to call it “focused thinking” as it may appear as ordinary problem-solving, ruminating, pondering, etc. It is important to let this kind of thinking go on, for besides there generally being quite a bit of momentum behind it, it is how our minds will eventually become “intelligently engaged” in looking at things.

This whole area of “focused thinking” in meditation is fraught with difficulties. Practices from the East generally advocate “transcending thinking” as opposed to thinking as being part of one’s practice of inner understanding. Western traditions are generally more sympathetic to “focused thinking”, and our verb “to meditate” does mean “to ponder, to contemplate, to reflect on.”

Pondering, reflecting on, and contemplating are all forms of focused thinking, for they require some sort of concentration (sustained focus on something). When these are turned into meditation practices, they are usually given with “objects” to be pondered, contemplated, or reflected upon. What Eastern practices have to offer in this regard are ways to become aware of the act (or process) of focused thinking. But what is often missing from such practices is the allowing of focused thinking about things, from which the nature of focused thinking can be observed and studied.

Allowing one’s mind to engage in focused thinking as part of the meditation sitting is thus a condition for any serious exploration of the process of thinking, though at first it will appear more as a hindrance or impediment than as an asset. This occurs for a variety of reasons. The most common reason is that meditation is about “meditative states” and “focused thinking” is not generally considered to be “meditative”. Such a view on thinking effectively fosters aversion to thinking, where there is no room for gentleness. Another reason is that the experience of sitting and thinking appears to be no different than idle day-dreaming. That is true. There may be little difference for some people between the experiences of “thinking in meditating” and day-dreaming. What distinguishes these two mental activities however is that meditation is done with the intention to develop more awareness of one’s inner world while day-dreaming is done to pleasantly distract oneself. One last reason why most meditators see focused thinking as an impediment is that it generally carries with it a “self” which one is not entirely pleased with in meditation (but, for the most part, fine with outside of meditation). It is the “mundane self” behind the focused thoughts that one truly wants freedom from in meditation. Only, the route to such freedom is not to be found in the aversion to thinking, for like the many-headed Hydra, once one head is severed, two new ones grow (one is the newly reconstituted train of thought and the other is the judgments about the self that does the thinking).

How to Begin Meditating with Interest

A. Sit, recline, or lie down in a comfortable posture. Close your eyes. Let yourself think. Don’t try to think about anything; just let your mind think about what it will.

B. During the entire sitting (15 to 30 minutes), try not to move your body or limbs. But if you have to move, do so slowly with forethought.

C. If at any time in the sitting your thinking becomes fragmented, random, dreamy, or just less prominent, then allow those experiences to continue (instructions for the condition of gentleness can be used here). When focused thinking returns, for surely it will at some time, meditate with permission to do whatever you see as needed. If you need to go with the thinking, go with it; if you need to “let go” of the thinking, let it go on and subside of its own; if you need to explore it, let yourself think about the thinking that is going on of its own.

D. At the end of the sitting, take a few minutes to recollect what you were thinking about during the sitting. Try to get a sense of the general themes of your thoughts (work, relationships, plans, memories, etc.) and how these themes shifted in the sitting (from work to relationships to memories, for example). You need not write them down, unless that helps you with your recollection. And, you need not go into any detail with your recollection; it is enough, at the beginning, to just become aware of the general pattern of your “focused thinking” in the sitting.