I'm actually in a similar situation. I'm moving into the city for this upcoming semester, and I happened to get really unlucky in that at the start of the summer, I had a boss who was cutting pay out of my paycheck and generally telling a lot of lies to keep me on and waiting for the big bills to show. I just recently quit, and I essentially spent all the money from that job just to keep gas in my tank. Now I'm looking for another job, but I have my first ever meditation retreat (Goenka) in 10 days, so I'm nervous to apply for a job when I'll end up being gone for 10 days and possibly miss callbacks. Either way, once I get back, I'll have 3 weeks to find a job and make some money before I have to move in, and then there will be a full credit load waiting for me at college, plus the need to work that much more. So I've actually been thinking about these things too. It seems tough sometimes to balance effective practice with "the real world". Practice costs time and effort, and "the real world" can already take a nice hefty chunk of your time and effort. And all the while, the question is of happiness... which pursuits will actually make me feel secure and at a good place?
I've decided to stay with going on this retreat. I'm not sure what your current setup is, but even if I can get away from my daily routines and responsibilities enough to pack in some intensive seated practice, I've definitely never had the chance to spend ten days in relative silence, practicing all day, with nothing else to pull me away, surrounded by people who have some sympathy for what I'm doing.
I’m strongly leaning toward this gear-shift toward the external circumstances rather than turning inward again.
I can feel ya on this, I have this feeling sometimes. You said it was a jhana retreat... I think jhana can act as a bridge between morality and insight. You can take your mind after jhana and stick it into going through some unusually deep cycles of insight, or you can take it back to the drawing board and form plans/intentions/resolutions for your life. Typically, I've taken the former option, as I'm very interested in making progress in insight when I'm able to, but I ought to take the latter option more often, since in the end, morality is the level at which there isn't any point to stop developing, or as Daniel says, morality is the first and last training. I'd say... go for the retreat! Then use the sharp mind to hone in on whatever intentions or resolutions you'd like to make for your life.
Good luck with it all! And also, thank you for all your great advice in the past.