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Hey Cruzzie,
I think you are very insightful and doing some serious investigation! Often people who have suffered a lot in life are drawn to meditation and really stick with it because life has provided a rude awakening, and that sounds like what is happening for you, it is called shunyata, or emptiness, groundlessness, or feels like the rug has been pulled out from under you. While it is very scary, and unnerving, it could also be the beginning of a beautiful relationship with yourself, loving and accepting yourself for everything you are with unconditional friendliness and steadfast loyalty no matter what. Initially meditation will make you aware of buried sadness and pain. This pain has always been there but because of the noise in your life/head, (and not being still) it could not be heard or truly felt, but it has been trying to be heard and it would have been showing up (sideways) in your life whether you noticed it or not… So the crying may be healing and cleansing, that needs to take place, but the good news is it is healthy. So initially meditation can bring a lot of confusion and can feel claustrophobic, but this slowly turns into more clear seeing and spaciousness.
I like that you said fear might as well be your best friend. How would you treat your best friend? Would you smile at them and welcome them in, ask them how they are doing today, offer them a drink, make them comfortable? As you move closer to yourself you are going to experience raw feeling and emotions for sure, but here, the instruction is to drop the story line and stay with the breathe or energy. Remember emotions are just energy we attach a story line to, without the story line the emotion can only last 1min 30s in the body. Try to stay at the pre-verbal level, what is going on there? You may find anxious feeling are actually excitement misinterpreted….
While I was reading this it immediately reminded me of Rumi, who puts it so beautifully:
The Guest House
This being human is a guest house.
Every morning a new arrival.
A joy, a depression, a meanness,
some momentary awareness comes
as an unexpected visitor.
Welcome and entertain them all!
Even if they are a crowd of sorrows,
who violently sweep your house
empty of its furniture,
still, treat each guest honorably.
He may be clearing you out
for some new delight.
The dark thought, the shame, the malice.
meet them at the door laughing and invite them in.
Be grateful for whatever comes.
because each has been sent
as a guide from beyond.
— Jellaludin Rumi,