Humans are by nature a spiritual/physical/mental/emotional complex and of course, so much more and please allow me to simplify for this discussion.
To engage with our spirituality by stepping onto our own Wisdom Path is to often engage in a world that is non-linear. It is not rational and therefore, does not think like a human thinks. We humans think based on our persona, psyche, ego which is the conscious, rational, logical aspects of our mind. Using our logical reasoning is just a fragment of the way we process this material experience and is impossible to use to access Spirit.
We can also perceive beyond our minds with our intuitive faculties which touches the realm of Spirit. Every human possesses intuition which goes beyond mind and many of us do not choose to exercise this inherent ability leaving us to question Spiritual happenings through our logical minds. We are dumbfounded by Spirit's non-linear nature.
You can only engage Spirit by going out of your mind, that is, not using human thinking or human rationale. Spirit does not think with a persona, psyche or ego. Spirit just is and that is why man has discovered ways to engage with Spirit such as meditation that quiets the mind so you can hear the whisperings of Spirit.
Part of the very reason of being on a Wisdom Path is to engage with Spirit and leave mind. You cannot expect to ask Spirit questions based on the workings of the rationale and get answers that fit into a neat little mental box since Spirit exists outside of that box. I am asking you to pay heed to this.
If you continue to ask Spirit questions using logical, human thinking, you may end up frustrated. Use meditation, your intuition, to engage with Spirit and be willing to learn how to decipher the ways of Spirit. It will save you much consternation and confusion.
Being a Wisdom Keeper, to me, is becoming adept in the ways of engaging Spirit. Go out of your mind in the good way of not losing it and find Spirit on the other side.