First time poster here! I’ve got a layered question, firstly, at the level of the constructed observer mind, which if I am understanding correctly acts as a launchpad for its eventual own dissolving, what would you say are the shadow side characteristics of identifying as observer, decider, doer level other than it still ultimately being an illusion, what could it potentially do to keep you stuck at the level of the observer? And I ask because I have a follow up question to this that I feel is more clear if I first generate some answers to this initial question. 

I sincerely appreciate any and all speculation, feedback, or perspectives on this question, and especially any corrections as I finally decided after many years of clumsily seeking, to become an active member of this community due to lack of places I can go with dharma talk in my personal life. (Other than my own mind) Im excited to begin to engage with you all and take a proactive step on my path.  

Welcome Daniel, it's great to have you with us!

What I have found is, the sense of self can shift in ways you wont expect. Eckhart Tolle had me talked out of believing I was thoughts - then I came to believe my true self was consciousness.
..but consciousness stops every night during dreamless deep sleep, doesn't it? And there are people who can attain niroddha samapatti, and yet we are still the same after temporarily losing that consciousness.

So I came to believe I was pure Will. Then I noticed my will was not always activated. So I thought I would be the source that originated that will. But I can't find that source within my senses.

Now when I do insight meditation, observing the characteristic of no self, what I find feels the most as me, is an energetic contraction somewhere behind and between my eyes. When I observe that even more carefully, it feels as if it fades away, and the sense of self is the border separating outside world and inside perception. The jhana states warp this, just to add to the confusion.

It might be worth noting the idea is not to eradicate the sense of self, it's rather to realize through direct experience there is no separate and stable sense of self.

Oh by the way, if you would like to have guidance directly from someone deeply practiced within dharma, you can freely contact Daniel Ingram, Beth Upton and Dhammarato to talk one to one. Those are just the ones I know of, they are all wonderful teachers in their own way.

What construction of sensations can notice another sensation?
​​​​​​​There inlies the shadow side, investigation solves this construction problem that pops up over and over.
good luck,
​​​​​​​~D

Shorter answer - fear and uncertainty.

Longer answer - The "observer mind," by which I assume you mean the constructed sense of self, can be a siren (in the Odysseus sense) for maintaining the illusion of a permanent self that spins a narrative putting itself in control of all reactions and inter-relationships in your experience. This is a habit formed from years of living an unexamined life. The observer believes it needs to control everything because otherwise there is risk, no real safety, and potential death. The illusion thus created can serve to prevent careful, determined investigation (vipassana meditation, for example) of what's really going on, and the eventual dropping of the illusion that the observer is a permanent thing in control of its destiny.
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