Workbook and Crying

The following sentences were included in the response to my original question-
-Curious why you are thinking you’re not already feeling your feelings and processing them.
-What if you were supposed to cry…because you are feeling your feelings that your thoughts about your workbook work are creating?

What I am concerned about is that the thoughts have been around for a couple of years and crying about them off and on has been my experience for over a year so that seems to me like I am not processing them.
I feel like these thoughts and emotions are holding me back from establishing a vocation and home base (I am single and have savings but no income) and keeping me from confidently moving forward in life. If I’m supposed to cry, when will it feel like it’s helping and not hindering me?