[gbds3jewels:]
Emptiness is my opinion is one of the hardest thing to understand and perhaps not even supposed to be understood by only realized.
While different Buddhist schools may have different views on this topic, the view presented by Je Tsongkhapa and his followers is that first one should develop an intellectual understanding of the meaning of emptiness, and then one should meditate on that meaning, until one realizes it in a direct and non-conceptual way.
One can read so many explainer ion of emptiness and actually quote and explain exactly like Heart Sutra or LAMRIM but in my opinion as much as people explain it and describe it in text it is simply impossible to comprehend.
I believe that one should not be discouraged in case one does not manage to immediately make some sense of one or more explanations about emptiness. Thinking about the immeasurable benefits of understanding reality, one should patiently and persistently try to make sense of whatever teachings one could obtain, and gradually their meaning will become clearer.
Sometimes the problem may not be a lack of wisdom, but just a lack of patience and of persistence!
I'm have my reservation about having emptiness being discussed or studied as an "academic" subject.
The Buddha himself and the great Buddhist teachers, such as Je Tsongkhapa and his followers, offered a great many detailed and precise explanations about the meaning of emptiness, and as Buddhists we have the precious opportunity to listen to, or to study, such explanations, and then to ponder on them by ourselves, and to discuss them with others, in order to clarify our understanding, until eventually, through meditation, we achieve a direct and non-conceptual realization of emptiness.
For as long as this endeavor is motivated by love, compassion, and bodhichitta, there is no chance that it will degenerate into some dry, academic or merely intellectual useless exercise. Therefore, we should always check the purity of our motivation!
I think it is only meant to be meditated upon and realized.
In general, all of the Buddha's teachings are supposed to be listened to, then pondered on, and only then meditated on, and the teachings on emptiness are no exception. One cannot ponder on what was not previously listened to or studied, and one cannot meditate on what was not previously clarified and understood through pondering.
If one needs to meditate on emptiness, this is precisely because one still lacks direct and non-conceptual realization of emptiness, that is, one's understanding of emptiness is still merely conceptual; now, if such conceptual understanding, besides being merely conceptual, is also mistaken, or rather a misunderstanding, trying to cultivate it through meditation will only reinforce such misunderstanding and increase one's ignorance!
Therefore, one should spare no effort to develop a correct intellectual, or conceptual, understanding of emptiness, listening carefully to reliable teachings, pondering on them by oneself, and discussing them with others, always with a pure motivation of love, compassion, and bochichitta, and then, once the meaning of emptiness becomes clearer, to meditate on it, until one achieves a direct, non-conceptual realization of emptiness.
I have read testimonials from monks/nuns who have done prolonged retreats that knowing too much about emptiness academically may actually become a hindrance to actually understand what emptiness is.
In general, analytical thought is a hindrance to the meditational achievement of tranquility, or calm abiding. Therefore, when one emphasizes the meditational achievement of tranquility, such as in a retreat, one should indeed avoid too much analysis.
However, if one wants to achieve tranquility or calm abiding on emptiness through meditation, one needs, as a prerequisite, a correct understanding of the meaning of emptiness, which is the object to be meditated upon, and such a correct understanding is only obtainable through listening to correct explanations about emptiness, and then pondering on them, which is an analytical activity.
Once through listening to and pondering on correct explanations about emptiness one has obtained a correct understanding of its meaning, one places the mind on such meaning, and then progresses through the nine stages until one achieves tranquility or calm abiding on emptiness, which is the basis of every further development, such as special insight, until one achieves direct realization of emptiness.
As followers of Je Tsongkhapa, we are fortunate to have all such steps clearly explained to us, so that we can progress safely and smoothly step by step on the bodhisattva path, knowing precisely what to do and what not to do on each step.
Understanding this, we increase our confidence in and devotion to the Buddha, Je Tsongkhapa and our personal gurus, which is the beginning, middle and end of our bodhisattva path.