Hi Rob,
Really glad you posted this thread. It reminds me of a lot of the things that I have gone through over the last few years and you've encapsulated some of it nicely. To be honest I'm still not even sure I know what DN is or even if I've gone through it or indeed am still in it. If it includes such things as depression, anxiety, uncertainty (especially as to where you fit in with this society), loneliness (at times) - maybe all of the above then yes, sure I've experienced my share of DN woes.
I happen to be one of those who has made some major wreckless decisions in DN (like bailing on my software engineering career). I'm not really sure how to deal with those decisions, but am working through them. I still have some issues with society. Like having to work 40+ hours a week (I find that exhausting). And, I'm not real sure how that's going to play out.
With hindsight I did something very similar to you in 2008. I quit work completely, felt sure I was going to become a Buddhist Monk. Went on Pilgrimage to India/Nepal (visited all the holy sites) whilst at the same time feeling rather uneasy and thinking "what the f**k am I doing here?". I kinda felt I had to go because "that's what everyone does". I didn't take to India, and although there for 4 months, honestly I was only in the "real India" about 4 weeks or so in that time which was enough (the rest sheltered in Vipassana Centres or monasteries). I didn't really feel remotely connected during the time I spent there and felt sheer relief when I touched back down in England.
I was not unfamiliar with travel or even living in foreign lands having spent a considerable amount of time in S.E. Asia before this period and even lived in Bangkok for a couple of years in the early 2000's. But those SE Asian countries are tame compared to India...
Then I spent a period of time on and off at Amaravati (which is a well know Thai forest monastery in the West and used to be headed by a well respected American monk, Ajahn Sumedho, until he "retired" from being Abbott at the age of 76 I think).
Well, after all that, I'm still a layman and still not working (yet) I may go back sooner or later.
I personally want to have time for yoga, play guitar, and have time to hang out with people once and a while. I don't know if that's asking too much. I just don't see how all of that is possible working so much (and having to commute).
If you want my pennysworth, don't give up the day job just yet (re-reading what you said, sounds like you already have)...it can still keep you grounded to a certain extent. If it's possible for you to go part time, even if it means switching jobs/career to a 2 or 3 day week, I'd advise that. If you're not in debt and can afford to do so of course. Plus, you would be suprised at how much less you can get by on compared to the average Joe when you're just not part of the consumer culture.
I would absolutely second what Katy says:
However, there is a bit of a challenge in dealing with explaining oneself to others. So what are you doing? Meditating? You quit to meditate? And then the months go on, temper is still lost, dissatisfaction still arrives, boredome still arrives, the winter-ready squirrels seem brilliant all of a sudden and, whee, we've left the well-known shore to try to enter the so-called stream???
Explaining yourself to others. Forget it. The rest of the so called "normal" world cannot and will never understand what you are up to. You might even find yourself dropping certain friends, either deliberately severing ties or just kinda drifting away from them. However, with family that's almost impossible to do (and probably not meant to be that way anyhow - afterall, whatever you're going through, especially with regards to most parents - they did give you an awful lot especially in the first 16 or so years of your life). I say almost because there are probably a small number who sever ties with family as well. However, if that can be avoided I don't think it's necessary. It's also somewhat cruel. Remember that they don't actually need to understand you or what you're going through no matter how much you would like them to.
Perhaps some of what I'm saying is not relevant to your particular situation anyhow...
The good news is that I can see similarities in the Buddhist texts
Great. Do you have any sources/references you'd like to recommend? I'd be interested to read that too.
I wish you every success in your journey. Remember, it's important to also be kind to yourself too especially when things are getting rocky. Self Metta, can be a great help.
Piers.