Where does the Path begin?

"It's a dangerous business, Frodo: going out your front door. You don't keep your head, there's no telling where you could end up." - Bilbo Baggins, The Fellowship of the Ring

I'm impoverished. Not merely for lack of funds, but from a lack of imagination, and of trust in myself. The Romantic ideal holds that all anyone... boy or girl, man or woman... ever need do to find adventure, fame, fortune and a Place In The World, is simple: pack a bag, walk out of one's home, and keep walking.
The riddle should be easily solved on the face of it: nothing worth having can be obtained by remaining within the familiar. Therefore, one must leave as much of it behind as possible in order to find something uniquely one's own. The warnings against the practice work on the metaphorical level, as well: if you don't know what you're doing, you could get lost or hurt or robbed or otherwise come home empty-handed, assuming that there's a home for you when you do come back.

But without risk, without testing one's skills as a way of testing one's resolve and character, what is human life but a series of cages?

Should I divest myself of every material item, save those which I can carry easily (amounting to absolutely no more than, say, forty pounds in all) and Seek My Fortune at random? Or is there some middle ground, perhaps choices unique to me, that may be more effective?

I have previously fantasized about suicide in many different ways. It could even be said that I avoided that end through the simple expedient of an inability to choose from many possible methods. Simply moving until all strength to continue is exhausted seems like an over-extended way of doing exactly that. Ironically, not moving in the sense of remaining precisely within my "rut" of sleep, work, eat, repeat until death, could result in a life very similar.

"If your life were made into a book, would anyone read it?" This sentence frequently sees use as a way to goad the listeners into taking risks or attempting something new. The technique fails to move me because I have no interest in entertaining those who follow with the story of my life; I will, after all, be dead and unable to appreciate their responses, positive or negative or even merely confused. On the other hand, asking if I am satisfied with my life as I have lived it offers very little motivation, either; while the question requires a certain degree of reflection, it does not provoke action, either to continue support for the current pattern or to set up a new one.

The modern phenomenon of a "midlife crisis" usually includes something of a set script, in which the sufferer randomly abandons certain elements or the totality of the previous external existence in hopes of achieving something more satisfying. It can be as minimal as purchasing a motorcycle (as a symbol of "individual freedom" or at least changing previous habits) or as extensive as faking one's own death and beginning an entire new life, complete with a new spouse and possibly children. The Romans believed that the entire body renewed itself every seven years; the Japanese artist commonly known as "Hokusai" held a funeral for his previous self on his birthday and chose a new name and identity for the subsequent year. Perhaps this could be the beginning of a useful answer?

What's so scary about that?

There's a wonderful webcomic based on the protagonist's extremely non-literal search for pieces of his own mind. It's called "Alpha-Flag". One of the more interesting details is that the protagonist's "missing pieces" are all given names based on the phonetic alphabet; his lost self-confidence, his only companion, is called "Charlie".

There is at least one short story that may or may not have anything to do with the main narrative, whose title inspired this post:
http://joncairns.net/AlphaFlag/wordpress/?p=1112
Frankly, I've lived so much of my life alone and forgotten, or at least ignored, so the prospect of dying under those conditions doesn't bother me all that much. Have I gotten to this place because I'm so afraid of emotionally investing in other people? Or because I don't know how to find those in whom I can emotionally invest and who will do so to the same degree to me that I do to them?
It's probably got something to do with my poor track-record of self-acceptance. One of my previous therapists gave me a handout, some photocopied pages from a book called "The Principle of Self-Acceptance". In it, the author proposes that true self-acceptance is the absolute foundation for self-esteem and, ultimately, all healthy psychological states. It is defined as "my refusal to be in an adversarial relationship with myself".
I didn't read the handout when my therapist gave it to me, and I probably would have forgotten it if it hadn't somehow drifted to the top of the pile of clutter in my room.
"I cannot be truly for myself, cannot build self-esteem, if I cannot accept myself."
That's the last sentence in the handout. The rest of the handout talks about the need to accept all my thoughts, feelings, desires, actions and dreams as an expression of who and what I am at the time that these things took place.
Which would be fine, except that so many of all these things are simply not acceptABLE. I don't want to accept that I thought about killing myself or someone else. I don't want to accept that I feel like a waste of a life. I don't want to accept that I desire to make the pain stop by either running away from the rest of humanity and (briefly) living alone in the middle of the nearest uninhabitable wasteland. I don't want to accept that my actions form an almost schitzophrenic split between self-preservation and self-destruction. I don't want to accept that my dreams of financial security and emotional fulfillment are beyond my reach.
I judge myself unworthy of continued existence, yet I cannot match the courage of my convictions with actions OR rejection of this self-destructive pattern to make something better of myself.
I am too damaged to be anything more but I am not damaged enough that killing myself quickly is a viable option. So I kill myself slowly, through neglect; I will never make enough money to afford health care, and the mental health care system will not accept me until I am truly destitute... by which time I hope to be sufficiently ill that medical science cannot save me.

Lessons about myself

Right now, I'm basically stuck at home. I quit my previous job, thinking that I could just jump right into the swing of things with a new one that was already in the bag; papers signed, i.d.'s copied, the works. Come to find out that I still have to wait another week or three for a background check to work its way through the bowels of bureaucracy.
The practical upshot is that I have almost no money to spend on anything: fuel, food, purchased/rented entertainment... nothing. I've got supplies to last me a little while yet, so I'm not going to starve (thanks for asking).
But it's also been an interesting eye-opener.
I'm a writer. Which is to say, I want to make my living at spinning tales that other people will buy. I've got the raw "craft" part down cold, with grammar, punctuation, spelling, and so on. I've even advanced to the next level, where I can not only talk about "characterization", "pacing" and other scholastic writerly-things, but can actually demonstrate them in my own work.
All I need to do is have faith in my own ideas.
I've produced a lot of stuff that I've layered around the seed of ideas I get from someone else. There's no particular problem with collaborating on big projects, though I often take ego-hits from others as well as my inner heckler that they only give out Nobel Prizes for Literature to individuals.
Which might not even be true, and certainly isn't true for other prizes; Phil and Kaja Foglio have been jointly awarded Hugos, after all.
It's just the adversarial relationship I have with myself. "Who are you to even try? That's a stupid idea, you can't create an internally-consistent character or a society based on that" are pretty common jibes.
Wish I could come up with a better strategy for dealing with that.
Failing that, I wish I could find a way to earn a massive amount of money, so I could afford the kind of therapy necessary to help me deal with it.