There is something interesting in the Taoist canon, though I imagine many teachers in other traditions know of this.
People don't know why they should be practicing mindfulness. And then for whatever reason they gain insight -- be that practice, or ritual, or psychedelics -- they get it. A lot of things open up. There's a whole layer of meaning in textual traditions that opens up, and you realize a lot of people have been trying to say the same things. And you wonder how you missed it?
And then you want to go back. Now you jump into the practice diligently, to try to get back to that peak experience. The thing is, peak experiences are just that. Like all things, they come and go.
Coming through the psychedelics, it is easy to spend a lot of time taking hit after hit to get back to that peak experience. It was part of why people who have not been initiated into this fear it. They see people drifting out from the real world, and these people then say crazy things like, "well, reality is much bigger than you think."
The thing is, this happens in any mystical traditions. Someone who realized these insights while sitting on a cushion starts become uninterested in anything but sitting on that cushion.
Which is ironic because all of this is about experiencing reality, not escaping from it. That is another reason I pointed out the connection with vipassana. The point is to experience reality, something that seems counterintuitive when people talk about psychedelics.
Usually, you have a sangha -- people who are cultivating with you, whatever the modality -- helps you stay grounded.
Generally speaking, once you had some psychedelic experience, you'd find meditating much easier. It's the journey, not the destination. Of course :-)
It's funny that you say all of this, because I think it's completely true. I've never tried mushrooms, LSD, or any sort of hallucinogen beyond MDMA. MDMA alone changed my life, but what followed was how I utilized that moment of awareness that I experienced. I started meditating, read The Power of Now by Tolle, and having had enough of a philosophical and meditative foundation for understanding what Tolle was saying, I can occasionally enter a realm of understanding far beyond the shallow experiences I had lived in my life up to that point. It's so true when you say that reality is so much bigger than you think, because once you realize the ridiculous amount of depth that goes into every single thing around you (even the room your in contains materials built by dozens of people from across the world - think of how long it takes you to cook breakfast in the morning) then everything in your life begins to take on a sense of perspective.
That said, I really want to try mushrooms/acid because I feel like I'm at this midway point, bobbing back and forth between the awareness of meditation and the power of the present and slipping back into old thought habits and anxieties. I feel like a pokemon evolving, flashing between my old form and my new form and my ego keeps wanting to hit B to stop the evolution. :P
Cool! If you can, try mushrooms or acid with people coming with that intent. The setting and your intent going in matters. Best if your guide is someone who treats this as a sacred rite.
Something else that complements vipassana well is the method described in Tsultrim Allione's Feeding Your Demons.
But isn't meditation more like "You don't get it, until you get it" kind of a thing?
I mean I haven't read anything so far that describes the process of mediation as do Step 1) -> Step 2) .. All I get is description of what meditation can do and even that too more or less put down like- "You will not know how it feels, until you feel it".
How to Meditate? I hope someday I get some clear answer to this question.
How to meditate: a simple, permissive, breathing meditation. A nearly-identical form of this meditation can be found in most 'meditation-based' systems. Its pretty universal.
What you do:
1) Sit in a comfortable position, without shifting around, in a quiet place, with your eyes closed
2) Primary Focus: to constantly feel yourself breathing
3) Do this for about an hour
Likely Contingencies:
a) You "need" to shift around. Nothing wrong with that. What happens if you don't? Keep feeling your breath!
b) You will start thinking. Nothing wrong with that. But can you think while constantly feeling your breath? Or are you multi-tasking now? Keep feeling your breath!
c) a+b: You think about needing to shift around. Nothing wrong with that. Keep feeling your breath!
d) You might wonder if the hour is over or not. Alternatively, if you set an alarm, you will wonder if its properly set, and if maybe you should check it. Keep feeling your breath!
e) You might need to do a million little things, check the dog's water, the task queue, the pot on the stove, whatever. Keep feeling your breath!
f) You will find yourself thinking about how you are now 'feeling your breath'. Oops, you probably just stopped feeling your breath to think that thought. Keep feeling your breath!
What does it mean to "constantly feel yourself breathing"?
a) It means your attention/focus is completely on the feeling of breathing. Your conscious existence is the sensation of being 'a breathing thing'.
b) Corrolary: you probably aren't 'thinking in language'. In my experience, its not common to multitask thoughts 'in language' with a focus on physical sensation.
c) As you begin meditating (first several times? more? less? depends...) You will context switch back and forth constantly between 'thinking in language' and 'feeling your breath'.
Why is this meditation interesting?
The best reply I can give is, "Isn't it interesting enough that you can't just do such a simple thing as watch your breath without thinking about a bunch of other things?"
The process of meditation is just that, a process. It's not that hard. You're focusing on experiencing things at the base sensational level.
So for example, you have a web of thoughts associated with meditation and things like "You don't get it, until you get it".
There are feelings underneath that. Perhaps a bit of anxiety, frustration. Curiosity. Etc. Your mind interprets those feelings into thoughts.
Each feeling then, radiates from parts of your body. For example, anxiety may be a tension that you feel in the chest. It has shape, it has texture. It has pressure. Whenever you get those sensations, your mind automatically interprets that as "anxiety". So you focus in on the sensations instead.
So now, you're paying attention to the actual sensations. You notice that it isn't a solid thing. That it moves. And if you start zooming into it, it isn't a solid sensation so much as made up of tiny bits of sensations that come in and out very fast, and your mind interpolates the sensation to give an illusion of a single, solid sensation.
So now you're there, at the "bare-metal", bare sensation level. This is where you are, observing those sensations and not attaching to any one of them.
A similar practice is called "Noting". You pick a concentration object, and pay attention to it. Things will come up. First will be thoughts. You Note the thought, and then you go back to to the concentration object. Eventually, something will shift and emotions will come up. You Note each as they come up and then go back to the concentration object. Then you get to the bare sensate levels, and you Note each of the things that come up. Then you go back to the concentration object.
That is it.
There really is not much more than that. The insights some of the other folks have mentioned here, that will come on its own. Your "job" while meditating is to Note each and every thing that comes up, let it go, and then go back to the concentration object.
People don't know why they should be practicing mindfulness. And then for whatever reason they gain insight -- be that practice, or ritual, or psychedelics -- they get it. A lot of things open up. There's a whole layer of meaning in textual traditions that opens up, and you realize a lot of people have been trying to say the same things. And you wonder how you missed it?
And then you want to go back. Now you jump into the practice diligently, to try to get back to that peak experience. The thing is, peak experiences are just that. Like all things, they come and go.
Coming through the psychedelics, it is easy to spend a lot of time taking hit after hit to get back to that peak experience. It was part of why people who have not been initiated into this fear it. They see people drifting out from the real world, and these people then say crazy things like, "well, reality is much bigger than you think."
The thing is, this happens in any mystical traditions. Someone who realized these insights while sitting on a cushion starts become uninterested in anything but sitting on that cushion.
Which is ironic because all of this is about experiencing reality, not escaping from it. That is another reason I pointed out the connection with vipassana. The point is to experience reality, something that seems counterintuitive when people talk about psychedelics.
Usually, you have a sangha -- people who are cultivating with you, whatever the modality -- helps you stay grounded.
Generally speaking, once you had some psychedelic experience, you'd find meditating much easier. It's the journey, not the destination. Of course :-)