You know, these are really good questions (cf Part II below for your second paragraph)! One of the first things that occurs to me is how this kind of struggle or these conundrums are a good indicator of the need for a competent spiritual director. While it is not impossible to be emptied of inordinate self-concern and focus, it takes time and real effort, and one can only do so if one opens oneself discerningly to the world outside oneself and comes to depend on someone else's insight and capacity to reflect back regarding what they are hearing or seeing. If one doesn't have access to a good spiritual director, a good friend can often be helpful in the same way. The one seeking to change needs to be able to truly listen to others who know them and are aware of their flaws as well as their strengths and potential. It seems to me this is the only way to get out of the vicious cycle that otherwise ensues in trying to empty oneself of self. This is a beginning, and for me, I would say it is indispensable.
There is another related elementary principle involved here as well. Namely, the only way to empty ourselves of our false self is to open ourselves to the Creator God who makes real and true. But how we achieve this is important and paradoxical. Granted, we are not supposed to grasp at things. Rather, we are to allow ourselves to be grasped by the Mystery we call God and to not resist this. The imagery of emptying our hands so they may hold something else is helpful as a starting point, but it really is not radical enough. The truth is, we don't empty ourselves and then allow God to fill the emptiness. Instead, we allow God to gradually displace whatever it is that takes his place and fills us inappropriately. It is all God's work!
There is a story in the Gospels of both Luke and Matthew that illustrates this principle. A man is exorcised, and his house is cleared out, swept clean of an unclean spirit, and left empty for a brief time. The unclean spirit returns to the house, and it is then filled by even more unclean spirits than originally; the man and house are left in even worse shape than at first. Luke's point is that the human heart is meant to be filled with God/Love. It is made for that. What is counterintuitive, perhaps, is that in this case, this is only achieved by allowing God to displace the demons and fill the house (heart) as only God can. This is really all about grace and the salvific action of God, not our own, except to the limited extent that we must refuse to stand in God's way as we let him love and move us as he wills! The basic truth here is that only Love can make space for Love; only God can make room for God.
One's life needs to be focused on others and open to growing in one's love of others. Remember that, while it is focused on God and on living one's own self as fully as one can, even the hermit life is meant to be lived for others. This is important in achieving a life that is not solipsistic or inordinately focused on oneself. While I can't say whether it is harder or easier for someone living in community, it is somewhat different. One example might help: Recently, I was surprised to find myself writing about what is happening to this country and the current political situation. I have not done that in the past. When I explored this with my director, it became clear to me that I was not particularly interested in politics, but I was concerned with the state of this country, its people, and the terrible degree of pain that the administration's apparently careless and blatantly cruel actions were causing and will continue to cause as our democracy continues to be dismantled.
One person I know (a non-hermit) criticized me for my concern with all of this because it didn't comport with her notion of what hermits are to be about, but I recognized it as an instance of my own growth in compassion. At the same time, it led to a unique intensification of my prayer life in the hermitage and a careful limiting and focusing of my consumption of news. All of these factors led me to conclude that this was what God willed in my life, and I am grateful to be called to this as an integral part of my hermit life. I could have said no to this in the name of an abstract definition of eremitism, but again, it was about saying yes to love and discovering how that, in turn, enhanced and strengthened my life as a diocesan hermit. (This is another place c 603's requirement that the individual hermit writes her own Rule is critical for complementing the constitutive elements of the canon that apply to every such hermit. She must have experienced and be moved by love, and she must be free, within the limitations of her vocation, to risk herself for love.)
Yes, it takes some discerning to be able to negotiate an appropriate degree of reliance on and independence from others, but the only way to become less involved with self or "less full of oneself" is to become more involved with others, and specifically, to become more attentive to and loving of others while allowing them to love us. Jesus was called "The Man for Others," and those of us who want to become an imago Christi are called to the same vocation. I have sometimes heard people suggest that hermits are all about focusing on becoming holy and getting to heaven. As Cornelius Wencel, Er Cam, reminds us,
[[Not in order to achieve perfection does the hermit set out on his solitary voyage. On the contrary, he considers his way and mission to be part of a great common effort to change and renew the cultural and spiritual life of humanity. . . . So, we can hardly take a hermit for a person who limits his entire mission to a few prayers he recites and some daily routines necessary in everyday life. The hermit has to take into account all the difficult problems endangering the world today. . . . realizing how deeply he is rooted in the life of society and how greatly responsible he should be for the world and its future, the hermit wants to take part in coping with the difficulties and anxieties of today.]] pp 121-122, The Eremitic Life
And yet, even hermits cannot depend on God alone to speak to them in the way a good friend or competent spiritual director can and does. God does not relate to any of us, hermits or not, on that level or in that same way. Yes, God loves us each profoundly and communicates Godself to us intimately. God "speaks" to us in innumerable ways, including through others; occasionally, we may even hear a voice inside our heads/hearts that we can identify as God's own. Still, we all need to learn to listen to and trust 1) another human being whose competency is greater than our own and 2) our own consciences as the voice of God within us and our true selves (as opposed to our false selves). Even so, God is Mystery itself, and intimate though our relationship may be, it is not the same as speaking with another human being. This brings me to your second paragraph's questions.
Part II:
My last questions have to do with asking God about every little step one takes during the day. The person I am asking about is trying to "ask God about every little thing" she is considering doing. She even says she asked God, "May I go to the restroom or. . ." do another trivial task and what his will was in that. While I think that turning to God is important in becoming less full of oneself, this [way of conceiving of that] also seems self-defeating to me. She seems to me to be becoming even more full of herself in this way, but I am not sure I can explain why that is so. Do we only do the will of God by losing our own will? Are we to truly be emptied of ourselves and filled with God? Do you understand what I am asking?]]
The situation you have described of asking permission for every little thing was once the way some religious congregations operated in centuries past. It was abandoned as infantilizing, and rightly so. In those days, the novice or junior religious thought of the commands of the superior as the will of God**, and this asking of permission for every little thing was supposed to form men and women who were attuned to the will of God. Unfortunately, it backfired, and the religious found they were unprepared to make significant decisions for themselves, had badly formed consciences incapable of making prudent conscientious judgments except when told what they "should" do, and were incapable of hearing the will of God apart from the voice of the superior. Given that there is apparently no superior in the situation you describe, this also means that God is being asked to micromanage a person's life; God does not do this!!! This is why God gave us hearts, intellects, consciences, and wills. We are to listen to these, and yes, we are to allow them to be formed and shaped according to God's will. But asking God to tell us whether we should use the restroom or do another task first literally places us back before the days when we were potty trained!!!
What you have described is a literal example of a so-called "spiritual" practice that, despite its intention, infantilizes one!! And what it does to God is similar, for it trivializes Him and His role in our lives. Ironically, it makes things all about us again, and this ties into your original question. If we diminish God in the name of some flawed notion of "seeking his will," we divert attention from the real God and substitute ourselves and our own miniscule conceptions in God's place. We will never truly worship him in such a situation. J.B. Phillip once wrote a classic book called Your God is too Small. It was seen as a significant and common, even universal, error we make, typical of idolatry in all of its forms. In the case you describe, trivializing God, especially by infantilizing ourselves, makes us the center of the universe, something that always happens unless and until our God is no longer too small and we grow in relation to Him! That means, as you say but could not explain, the person you described is making things all the more about herself. Ostensibly, she claims to be seeking the will of God, but really, it is an elaborate charade (she may not even be aware of this), emptying the real God of His true role in her life and substituting a cosmic micromanager who "speaks to her" as she demands and is comfortable with. As I noted above, God does not speak to us on this level or in this way.
Neither are we asked by God to lose our will, but to allow it to be formed and shaped in communion with the loving will of God. That is what allows Paul, who has been crucified in Christ, to say, "I live, yet not I, but Christ in me." (Gal 2:20). Note the paradox in the sentence as well as the emphasis on personal truth. It is I, yet not I. It is really Paul who is alive, but it is Christ in Paul at the same time. Paul is essentially describing what happens when God has made us truly ourselves and freed us from the false self that once held sway. We become truly alive (and that means with our own will), but we are alive in and through Christ. I think this is a much better way of considering what happens and is meant to happen than thinking we are emptied of ourselves in some way that leaves us only a shell that is then filled with God. God wants a relationship with a person, not a receptacle, and he wants an adult who is capable of adult love, not an infant!
** Today, when a superior asks someone publicly vowed to obedience to do x or y, we still consider this a way God is speaking to us, but not the only way. We discern what this means for us and how we prioritize and will carry it out. If we need to pray over and discuss the matter, we will do that. We do these things not to avoid what is being asked of us but to be sure we have rightly attended to and understood what is being asked of us. Today, we speak of the ministry of authority and recognize that this is rightly exercised with love and should be responded to in the same way.