Michael I can tell you what I chose for myself.
I had a period when I was considering something similar to you --- throw everything away and just go meditate until it's done, then maybe teach meditation for a living or something of the sort.
Seeing where meditation actually seems to be leading me, in retrospect, that seems very silly. It is not easy to explain why, but I will give it a try.
A realization I had during this period was that everything was unsatisfactory. Nothing which I did seemed to bring any satisfaction; not my PhD, not my friends, not food, not sex, nothing. Then it came to the point when I realized that nothing that I could ever have would satisfy; I imagined multiple ways my life could be instead, from being a monk like you are considering, to being an all-powerful God living the ultimate stereoscopic hallucionogenic fractal metaphysical allmighty orgy. And I had the distinct sensation that none of these experiences would satisfy me.
And yet, nowadays I seem to be arriving at one of the most satisfying periods in my recent life, and, externally, hardly anything has changed since the time I had those realisations, things are mostly the same as they were during that period of my life when satisfaction was all but impossible to find.
So what happened? I am not sure. Tentatively, I explain this as having understood, to a large extent, the mechanism of desire, and thus the mechanism of satisfaction. I will now expound what I (believe to have) understood:
(Disclaimer: I am not certain about what I am about to write, I write as if I was for stylistic purposes)
What happens is the following: desire is a primitive mechanism for behavioral control. On a normal non-introspective conditioned mind, it works as follows:
(1) perception recognizes an object/activity/situation as being worthy of desire
--- this happens due to ingrained animal features; desire will typically be about something which is associated with individual and species-survival, e.g., the desire to amass or collect items, to eat, to have sex, to fulfil a social role (the protector, the wise, the powerful, the shameful/worthless/humiliated, the good, the bad, the obedient, the mother, the martyr, the adventurer, the provider, ...), to be safe from harm, to belong to the community, etc.
(2) then desire is momentarily intensified (it is usually present 100% of the time when one is awake).
Desire is an uncomfortable sensation, even desire for the things one wants is extremely discomfortable; although this is really hard to see, because desire for the things one wants is usually accompanied by somatic pleasure (thinking about sex feels good, although as any social misfit knows,
just thinking about sex eventually makes one feel lonely and sad).
(3) Now here is where one is fooled: one thinks that one will only be happy by getting the object of desire, and that "getting what one wants" is synonymous with "satisfaction."
(4) then two things can happen --- one gets the object of desire, or not. If one does not get the object of desire, then there are several possible outcomes, from "letting go" or "giving up" one's desire, to forgetting about it, or deliberately not thinking about it (desire might wane and disappear with time), to depression and suicide.
If one does get the object of desire, then this is not only accompanied by somatic pleasure, but one will also feel "satisfied" in return. Desire will again decrease in intensity and/or visibility (one does not desire what one already owns), and one will usually think "I got satisfied because I got what I wanted."
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But when one meditates, when one looks again and again at the workings of the mind, one might soon realize that one does not get satisfied by getting things. I think this is what happens on this "unsatisfactoryness" phase which you are going through --- you are realizing that "getting things" or "having things" isn't really satisfying in itself, and conclude that "things don't satisfy." Even things which brought satisfaction to you before no longer seem to "work" anymore.
This is what you are describing:
Michael:
So I'm not ready to let go of quite a few trappings of the world yet, and maybe I shouldn't anyway, but there is this sense that seems to grow over time that none of it's satisfying and none of it'll ever be satisfying.
This is a very common occurrence among meditators, and I got that too --- so what is happening here?
What is happening is that, after getting better and better introspective skills, one is no longer able to ignore the permanent presence of desire. It becomes obvious that one's mind doesn't work all that well --- it is noisy, and constantly whining that it wants things, and that it is unhappy, and that it will only be happy if it has this or that. The mind is not at peace.
To make it worst, one sees for the first time that "getting what one wants" doesn't actually shut up this whining, it doesn't satisfy the way it seemed to before. Chasing one's dreams, which once seemed like the purpose of life, now feels like a stupid game which can not be won. One feels that even if one had one's "dreams," one wouldn't be satisfied. This is the so-called "knowledge of disenchantment."
--- But in truth one can actually become satisfied, if only one understand what satisfaction actually is. And it is really very simple, it is just a matter of repeatedly observing what happens when one feels satisfied, and making a different causal link. What happens when one get's what one wants is that:
(a) one feels satisfied, (b) desire decreases in intensity and/or visibility (one does not desire what one already has), and (c) one thinks "I got satisfied because I got what I wanted."But what I have concluded for myself, and maybe you will too, is that
One gets satisfied, not because one "gets what one wanted," but actually because of the decrease in desire.And once you see this link, suddenly all stands explained: desire and suffering are one and the same thing. Suffering is the discomfortable aspect of desire, and desire always has this quality (dukkha, unsatisfactoryness), which might or might not be correctly seen. Desire is "the passionate craving that things are not as they present themselves right now," and the discomfort of
not wanting to be here is what suffering actually is. Desire comes in two flavors, the desire for something which isn't present (craving) and the desire against something that is happening (aversion). Furthermore, the mechanism of desire uses an ingenuous trick to survive: it actively distorts one's perception so that you can't clearly see the workings of the mind (ignorance).
Addiction, fear, anger, love, resentment, excitement, sadness, boredom, worry, compassion, etc, etc, etc, etc, etc, are all manifestations of desire. Without desire, what is left is (reportedly) a sort of innocent wonder, a perfect pure perception, and a complete and unparalleled satisfaction and fulfilment.
This is the point: all one's life we are taught that satisfaction is defined positively (when we get what we want), when, to be correct, one should actually define it negatively - satisfaction is the absence of desire. What you are getting in your life isn't satisfying you, because satisfaction is not about having more, it's about having less.
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Having come to terms with this in the past few months, and having started to navigate towards the extinction of desire, I can tell you that I have had results, in terms of being happy and satisfied right here right now, which surpassed my expectations in speed of attainment, quantity and quality. I've taken my happiness into my own hands. I see that sadness is just a bad habit, and boredom is just dulled attention. There's still plenty of work to be done, but I know what that work actually is --- rather than looking at it as some vaguely defined spiritual quest, I see it as a very attainable and worthwhile goal, and I'm having a good time getting there.
And finally, how has this discovery changed the way I plan my life, in particular my former inclination to give everything up and be a monk?... That desire seems so silly to me now! Life is really so much fun when you're not busy wishing it were somehow different! Why would I become a monk, and give up on all the good things of the lay life? "Being done" with meditation, for me, actually just means being completely satisfied with things the way they are, so it doesn't make sense, to me, to run away from those things into some monastery.
That is my own current perspective, I hope it helps!
Have fun!
Bruno