This is a warning about poverty of spirit. According to our interpretation it is nothing if it is not subjectively real. Subjectivity can only be good if it is in conformity with reality and objectivity. Thus, the quality of poverty of spirit depends on the quality of the understanding of inadequacy or lack.
Now, perhaps you see the problem emerging in that last sentence. An individual must be in good shape to understand well. Understanding sex or money or crack is not simply a matter of noting its physical qualities. One must note the value of the substance or the act. Its value is partially a matter of its essence (form) and partially a matter of its matter (context).
Further, what we want to do here is be aware of our lack. Lack implies measure of the whole. I do not know how much water a glass lacks unless I can measure the whole. It is from the whole that the significance of the lack is determined.
Here the whole is the human in its fullness and happiness. This I do not see clearly in my inadequacy. It is the fact that I am a mess that makes it impossible for me to know how much of a mess I am. Do not fret, but let us recognize the implication.
Implication 1: my first step of poverty of spirit recognition is going to be inadequate. This means it will need completing moving forward. I should expect for the first step to be inadequate and the approach to happiness to be inadequate even when I am taking the steps as effectively as possible. It is in the nature of things that I can only partially get started and my progress will be retarded by this problem.
Implication 2: setting aside the fact of the inadequacy of my recognition of inadequacy I should take ANY recognition of inadequacy as a suitable place to begin. Now, it would obviously be wrong of me to focus on the splinter when the log lays nearby, but to the degree that I am made subjectively aware of my poverty of spirit the path to happiness has been shown to me! That is cause for rejoicing.
Implication 3: Here I need to assume that progress is possible. If progress is possible, and the beginning is marred, then it must be possible for each returning to the logical moment of poverty in spirit at a later temporal moment to become better. There are reasons for such an expectation. First, progress is possible! You have likely seen it in your own life, and you have seen others take shape. Do not doubt that the wind blows though you know not from whence it blows. Second, there is an ancient bet that intellectual clarity of understanding and moral status are tied such that as one changes so does the other. As our souls become calmer and more temperate so we see better where we lack and our view of our lack is enhanced.
So, taking the first step of poverty in spirit will enhance the later expected return to poverty of spirit in order to repair the earlier inadequate recognition. But the later repair would not have been possible without the initial inadequate recognition of inadequacy.
A baby learns to crawl, then walk, then run. Then after much time it turns around and helps a new baby learn to crawl, walk and run. And so on.
In the case of moral development, setting aside other celestial helpers and remaining in the human only: your first inadequate recognition of poverty of spirit allows you to take further steps in moral development which allows you to see more clearly what you lack which allows you to return to the moment of poverty in spirit and begin again.
You are born physically. To be born spiritually is the second birth. And it happens every time you return to the recognition of lack and begin the process inviting that which would supply the lack. How is it possible? Don’t doubt that it is simply because you do not understand how. It makes total sense that we cannot understand how. We are inadequate understanders. Let’s get to work.