Hi Kelley, that does sound like the Dark Night of the Soul, or the dark night of the I. You have written a short story of yourself in the post, a short story of I. To transcend the I, the story needs to relax a little. ´Relax´ not like a body relaxes on a chair and lets a tension go, ´relax´ as in loosening the focus of your attention on the story of I.
If you re-read your post, you will see that I is in every sentence, everywhere. I is in great pain, I is suffering, I is tired of experiencing. Try to re-write your post: where there is ´I feel tired´ replace it with ´I feels tired´ , where you wrote ´I am suffering ´ substitute it with ´I is suffering´ . You are living and looking through the conditioned I; I as the subject. Take a look at the I. Instead of looking through it, look at it, as Ken advises. Take a look at that I from outside - turn I into an object. You will see that the I set a goal 20 years ago to get to a happy place through practice, mediation and discipline. The I made a mental picture of what the result would look like and got excited in the anticipation of that result. But the result is not coming. No kidding I is exhausted, frustrated and wants to get out of the situation. Ask the I how did it know what the result would look like? Did it read it in a book, or heard from someone? Who set the I’s expectations? Remind the I that the path, that the I now wishes it never set foot on, is about the trip itself, not about the result. Remind the I that meditation is only a practice; knowledge helps a great deal too.
That I is the psychologically conditioned matter, it is the stuff from which the development happens, spiritual and non-spiritual alike. If you re-write your post from the 3rd person perspective and re-read it, what you are looking at is a type-structure, it is a point of view, a story. That psychologically conditioned I is only one of the two selves that you have. And that one I, the conditioned matter, has usurped the focus of attention and directs it onto its current experience of the Dark Night of the Soul. Tough spot.
Maybe suggest to the I know that a purpose that it is looking for is to learn to notice where the focus of attention is. Wherever you place the attention, it will illuminate that part of reality, and the rest will fade out. Where is the focus of your attention now? If you are drifting from the thoughts to the feelings to the memories to imagination, you are placing the focus of attention on the story of the I, the spinning wheel of samsara. Your spiritual journey calls for the relaxation of the story, a shift in the focus of attention. If you can shift it onto the going ons of the I and look at as an object, in the moment, from a different vantage point, a transformation is on the way.