Question:
1- How can a person know what his current level is, being that our inner world is so hidden from us, and our level keeps changing?
2- Why should a person ever ask another for advice, if he can just discern his own level?
Answer:
1- Part of the solution to this lies in having a rebbi (Torah teacher). Chazal say to “make for yourself a rebbi, and be removed from doubt”. When choosing a Rebbi [to guide you in matters of Avodas Hashem], either choose a Rebbi who has the general picture (‘hekef hakelali’) about life, or, choose a Rebbi who has already traversed the particular issues that you are struggling with.
But in addition to this part, there is also your own “inner teacher.” Man’s avodah is to internalize his mind’s knowledge about truths, into his heart. As it is written, “And you shall know today, and you shall settle the matter upon your heart.” A person’s brain\mind is considered to be like the inner ‘teacher’ of man, which gathers all the appropriate knowledge about life and sees it (aware of it intellectually), and the ‘student’ within him that accepts the teacher’s information, is the heart.
With some people, their problem is that their brain and heart cannot understand beyond a certain point, and this shows where that they are not yet holding at that level. Others have a disconnection between the heart and brain, which means that they know a lot but they don’t act upon their knowledge. This problem is referred to by our Sages in the statement, “One whose wisdom is greater than his actions.” Others do have an integration between their mind and heart, but even so, their mind is aware of more knowledge than what their heart has internalized, so they are still not holding at the levels which they know of.
But if a person is always seeking to internalize his mind’s knowledge into his heart, before the mind has seen enough knowledge, although this is also an imperfect kind of avodah, such a person is still closer to acting upon those levels he knows about. It is not yet perfect, and he will still need to ask advice from another who can guide him to reach higher levels, or, he can get to those levels within himself and be able to reach those levels accurately, to some extent.
2-
If I have understood your question clearly, the answer is as follows. Although Chazal say that we must have a Rebbi, this obviously does not mean that we need to have a Rebbi for every last nitty-gritty issue that comes up in your life. Should a person spend the whole day on the phone trying to get through to his Rebbi whenever he has an issue? Obviously, there is some kind of deciding that each person needs to do, himself, without having a Rebbi at his side.
But the issue is: How indeed does a person know if an issue he’s facing is one that requires a Rebbi to answer, or if he should decide it on his own? This is a fine line that one must figure out himself - and there is no sefer that can define the rules of this.
Basically, the more a person matures in life, the more he can decide on his own without having to ask a Rebbi for an answer. If a person is not that mature in life, either he will always decide quickly, because he is immature and he does know how to really think properly, or he is a kind of person who will have to ask a Rebbi a lot for advice. Those are the two options that he will always find himself with.
Every person ultimately has situations where he will have to decide, on his own, how to act. These include the various situations throughout the day which force you to decide what to do, or, the situations where you have no idea how to decide on, yet even so, you have no choice but to make some decision. There are always situations which force us to decide on our own where we can’t ask anyone else. All of us go through such situations, some more and some less. So although we must have a Rebbi, there will always be situations where we have to decide on our own, and there is no Rebbi to ask.
When it comes to such situations, where we are forced to make a decision, we can decide using the power of daas. Our daas is actually a point above our own soul. We must use our daas and decide on things. Although we cannot ever be sure about our decisions, we have no choice sometimes, and we must decide. But if one makes sure to act more and more with purer intentions, he is granted more Heavenly assistance (a light of Hashem that guides him) to get to the truth.[1]
[1] For more on the power of daas and how it relates to making decisions, see Getting To Know Your Thoughts_08_ Connecting To Your Decisions, and Fixing Your Wind_013_Bragging Part 1 – The Need For Approval; see also Utilizing Your Daas_02_Deciding.
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