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?