Followup to: Understanding vipassana meditation
I explain how to practice vipassana meditation1 (a form of Buddhist meditation), giving instructions, advice, and measures of progress. By practicing vipassana one becomes aware of (and exerts control over) the process of affective judgment. This process may underlie important (and subtle) mental patterns of feeling that are responsible for common rationality failures. While I've tried to give helpful information, you should meditate at your own risk; you may experience mental instability or change in undesirable ways.2 This is a somewhat brief post containing information I've personally found most helpful on my meditative journey, see other guides (like this one) for more.
Decide beforehand how long you will meditate for, and set some kind of alarm to go off at the end of this period.
Start with 10-15 minutes; you can incrementally increase this amount to 30 minutes or an hour. The use of an alarm allows you to meditate without worrying about checking if your time is up.
Go to a quiet location where you feel comfortable. Assume a posture that you can stay in for a while. Do your best not to change your posture during the time period.
AFAICT the posture you choose is not especially important. You can sit Indian style, in a half-lotus position, or in a full-lotus position. You can sit on a pillow or directly on the floor. If none of these positions work you can also sit in a chair. You should be reasonably comfortable (but alert) and stable, and able to breathe naturally. Take care not to aggravate past injuries or cause new ones.
Close your eyes and your mouth. Breath naturally through your nose. Keep your awareness centered on the area below the nostrils and above the upper lip. Neutrally and passively observe the breath passing over this area3. If you realize your mind has wandered, patiently re-center your awareness. Once you have established some degree of concentration you should be able to "see through" thoughts and emotions without getting swept away by them.
You should not regulate your breath. If the breath is deep, simply observe that the breath is deep. If the breath is shallow, simply observe that the breath is shallow. Observe the breath neutrally and passively. Don't associate yourself with the breath.
The breath should be the center of your awareness, the anchor4 that you remain attached to regardless of what arises in the mind. Sooner or later you will get "stuck to" a train of thought, and lose your awareness of the breath. When you notice that this has happened, patiently re-center your awareness on the breath. Do this without feeling the slightest bit upset or disappointed.
After practicing for some time (hours, days, or months) you should be able to "see through"5 arising thoughts and emotions without getting "stuck to" them. Demanding thoughts and emotions will arise, and by "seeing through" them you maintain your observation of the breath as they continue (unattended to) in your peripheral awareness.
Advice
Meditate every day.
Really. You're trying to change deep mental habits of awareness and feeling, and that requires constant pressure and reinforcement. Consistency is important. Choosing to meditate at the same time and in the same spot can facilitate making it part of your daily routine.
Keep an innocently curious mindset.
Think of meditation as a wonderful opportunity to learn about your mind. It seems reasonable to expect your mind to be able to focus on one object for 5 minutes (or even 1 minute), and the fact that it's so hard for many people is interesting. Re-centering your mind, you might notice that you tend to get de-railed most often by thoughts about some past injustice, or about some future fantasy. When you remain centered on the breath, and are "seeing through" the arising thoughts and emotions, you may notice you think much more about some particular thing than you thought you did. Don't be afraid; unravel parts of yourself to become stronger.
Beware of wireheading patterns.
These patterns can occur in the form of trying to realize one's idea of what meditation should be (e.g. attempting to repeat a peak experience). This leads to altering one's practice in order to try to match previous expectations. This can be a subtle (and recurring) error, since one's meditation should actually evolve over time and through new experiences. Trying to follow the instructions as straightforwardly as possible, and looking for the manifestation of the benefits in one's life, can help to distinguish between wireheading patterns and genuine growth.
Measures of progress
Improved concentration.
You find that you are able to focus on tasks for longer periods without getting irritated or distracted.
Less anxiety.
On a coarse level, you get worried or stressed less often about macroscopic events. On a more subtle level, you aren't irritated by formerly annoying bodily experiences (e.g. cold or hunger).
Feeling unusual sensations (during or outside meditation).
You might feel spreading tingling sensations, numbness, muscle twitches, or a host of other surprising things.
Enhanced sensory perception.
You start to notice (and eventually continually become aware of) subtle sensations. You strongly smell trees and flowers when walking down the street, become sensitive to the temperature of the things you touch, etc. This enhanced perception is similar to the sensory sensitivity one experiences when taking psychedelics.
Insights about patterns of feelings.
You discover that you are perpetuating patterns that hurt you in one way or another. (See here for a concrete example)
Experiences of egolessness (during or outside meditation).
You find that you become absorbed in some aspect of your experience; you lose your sense of self and feel that nothing else exists. The first time I strongly experienced this I became absorbed in a sensation that was previously causing extreme pain.
Meditation during daily life.
You begin regulating your awareness and feelings as you do in meditation in the course of daily life.
1 There is much confusion out there about what vipassana is, and how it is related to other forms of Buddhist meditation (like anapanasati). I've made personal decisions about how to use the terms (and what instructions to give) in a way that I think is most clear and conducive to beneficial practice.
2 These courses indicate that they may turn down people with serious emotional problems. I expect that undesirable changes (if they occur) will be slow; you will see them happening and can stop meditating if you so desire. An example of such a change: I now very rarely get sad (didn't shed a tear at my last grandparent's funeral). This doesn't bother me at all, as I generally understand sadness as an indication of my attachment to how someone makes me feel, and not a measure of how much I intrinsically care about them.
3 At the start your awareness of the breath will not be very sharp. As it becomes easier to keep your awareness centered you can sharpen your awareness by focusing more precisely on the sensation the breath causes in this area, the touch of the breath, as you inhale and exhale.
4 I expect that the particular anchor you use isn't important (but I'm not sure). AFAICT in these courses your anchor is the mental procedure of systematically observing bodily sensations.
5 This guide has a good description of the difference between "seeing through" (being aware of) and "getting stuck to" (thinking) a thought:
There is a difference between being aware of a thought and thinking a thought. That difference is very subtle. It is primarily a matter of feeling or texture. A thought you are simply aware of with bare attention feels light in texture; there is a sense of distance between that thought and the awareness viewing it. It arises lightly like a bubble, and it passes away without necessarily giving rise to the next thought in that chain. Normal conscious thought is much heavier in texture. It is ponderous, commanding, and compulsive. It sucks you in and grabs control of consciousness. By its very nature it is obsessional, and it leads straight to the next thought in the chain, apparently with no gap between them.
I've created an open thread to discuss experiences and problems related to vipassana meditation, and to organize events and retreats.
(I think we agree, but it's not absolutely clear from your comment.)
When you ask, "What am I doing X for?", and get back "I want to achieve Y", it often happens that X is far from being an adequate answer to "How can I best achieve Y?", and so must be abandoned. Thus, even after figuring out Y, pursuing the question of "How to best use X for achieving Y?" is a strictly worse option than just "How can I best achieve Y?"
I completely agree.