A worthy question, A, but without going into too great a detail, the path I speak of (and the one I used to walk) doesn’t necessarily or even ideally mean embracing chaos or abandoning the security of rational decisions.
Gurdjieff’s Fourth Way and various other methods of exploring the mind/spirit/whatever-it-is don’t mean abandoning mundane social contributions. That doesn’t mean it doesn’t require great sacrifice, though, primarily in terms of time spent on recreation and things of that sort.
But, beyond that, an unfettering of the mind…Christ’s “Live in the world but not of it”…the Buddhist transcendence of material concern, and all that jazz, stuff I’ll not go on about because I don’t feel too comfortable making my view of reality fully public.
I do not believe being a seeker means abandoning social roles, and in fact being a true seeker MAY mean embracing those social roles even more fully, while staying mindful of other things.
To the last part of your question, I have always been guided much more by what I believe is right than by what what I want in the sense of personal gratification. I’ve been working since I was 14 and I would, literally and without hyperbole, starve to death before I’d take handouts from anyone. So, even in my most exuberant flights of fancy, I’ve never seriously considered quitting work altogether, but it’s out of my sense of the “rightness” of self reliance and not because I enjoy buying bullshit. I actually make decent money and still drive a piece of shit car (ha).
Anyway, that got a long rambling, but your question was worth taking seriously.