Hey Matt, welcome to the forum!
I remember having the same kind of experience when first rolling up my sleeves and deciding to apply the actualism method.
All this conditioning seemed like this giant mountain in front of me, and I was to go through each and every piece of the rubble, one by one, until the whole thing was gone 
I would read Richards journal where he wrote that one must investigate every belief, theory, custom, moral etc and think that he must be joking or exaggerating for it can’t be possible.
And funnily enough this is exactly what happened in the end, that mountain, one by one got reduced to a rather small pile.
But you don’t have to wait until the end to reap the benefits, they happen incrementally along the way. Because each and every piece of conditioning that falls away makes life that little bit purer and cleaner. And the cool thing is that you don’t have to worry about the ‘big picture’ too much, just the next thing that obviously comes to attention.
I can also relate to this, because if all this conditioning (societal as well as instinctual) is who ‘you’ are, then currently all of your identity is slanted away from the felicitous and innocuous and towards the doom and gloom. A large part of this is simply down to habituation though, it’s just ‘who’ you have been for so long that it has become ‘normal’.
But as you continue to apply the method the scales will begin to tip, you will begin to slant further away from doom and gloom and more spontaneously towards ease and happiness.