If thou have love and delight in the having and holding of anything that thou hast, how mean soever it may be, with the which love thou feedest thy heart for a time, or if thou have a desire and yearning for to have something that thou hast not, with the which desire thy heart is disquieted and stumbled through unreasonable thinking of the thing, that the pure desire of virtue and of God cannot rest therein; this is a sign that there is covetousness in this image. And if thou wilt put thyself further to the trial, look if anything that thou hast be taken away from thee by violence, or by borrowing, or any other way, so that thou canst not get it again, and for this thou art disquieted, angered, and troubled in thine heart, both for the loss of that thing which thou wouldst have again, and canst not; and also art stirred against him that hath it, to strive and chide with him that may restore it, and will not, this is a token that thou lovest worldly goods. For thus do worldly men when their goods and riches are taken from them; they are heavy, sorry and angry, chiding and striving with them that have them, openly, both by word and deed. But thou dost all this in thy heart privily, where God seeth, and therein thou art in more default than a worldly man; for thou hast forsaken in appearance the love of worldly things, but a worldly man hath not so, and therefore he is excused, though he strive and pursue for his goods by lawful means, for to have them again. (John Climacus)

Because I am worldly I am excused, according to Climacus.

But why would my open covetousness, acquisitiveness, and striving be less of an impediment than the hidden disquiet of the monastic?

Other than God all is ephemeral. Attachment to any ephemeral thing will be a source of regret.

Regret can be - often has been a - motivation for further opening to God.

I am, and most of us are, paradoxical, contradictory, and inconsistent. But if in this mix there is authentic love of God and neighbor, even chiding and striving can, eventually, lead to a deeper relationship with what is good, true, and beautiful.