I will be really curious to see how it plays out with this guy. He has been very nice and thankful the two days I've been there. He doesn't care when I come in (time or days). He seems disorganized and reactive, not a planner at all. I am crossing my fingers that he is just so excited to have this stuff off his plate that he leaves me alone to do what needs to be done... but there are also some signs to the contrary, so we'll see.
Your realization that you just don't fit in with your group because all the people you did like moved on is really interesting. Do you know why those women think your group is fun? From your description, it sounds pretty tedious - not enough to do, a scatterbrained boss who likes doing the work better than managing, semi-isolation/team-disconnect as a result of working from home. Are these fun people working together more closely?
In terms of stepping away from the day job, it was definitely a process. I saved 2-3 years of living expenses excluding my retirement accounts. I grew up poor and have miser tendencies, so that part of it comes easily to me. I started teaching myself to tolerate risk by gambling in the stock market.
I also had confidence that I would be able to get any sort of job to pay my bills if it came down to it – and I have *always* wanted to have my own business, at least as far back as my undergrad days.
I walked away from a job that had some pretty good benefits. 3-5 weeks vacation/sick time, free parking in the heart of downtown, a ‘nice’ office and building, free health insurance, bonuses that were sometimes 10% of my salary… but it was still a miserable job and they were starting to claw back some of those things. Even though the money was good, I was still underpaid for what I did – but stupidly believed that I couldn’t do better and had no idea what the market rates actually were for my work.
At the time I ‘mutually separated’ from that horrible job (unemployment!), I felt like any other job I took would be less money with worse perks. Now I will probably have the same net base salary while only working three days a week – and no unpaid overtime!
I’m not trying to talk you into quitting your job – there are some definite advantages to it, but the advantages are also disadvantages (working from home (isolating), not enough work (demotivating)). I just found that in hindsight, I wish I’d had courage to change my situation sooner. Just because your job looks good on paper or makes rational sense doesn’t mean that it’s actually good for *you.*
Anyway, just being open to possibilities, open to the idea that maybe if you are unhappy with this job, it’s okay to look for another one even if that doesn’t ‘make sense.’ I agree that all corporations are screwed up in one way or another, but it’s easier to live with some kinds of dysfunction. Maybe it’s time to give that woman a call? It’s been over a month since the holidays ended. What if she hasn’t gotten back to you because she is slammed with work and would jump at the chance to have you transfer?!
I’ve done the same thing with parallel parking, had someone else do it for me

I actually get worried about getting *out* of spots, so I prefer to do it myself. And what about car ferries?!
I volunteered for a conference last summer. I got there and they handed me keys to a huge pickup truck and told me to drive somewhere. I refused! I drive a small car and couldn’t imagine driving a pick up truck, especially in a place that was unfamiliar!
Someone hit and run my car yesterday and obliterated my side mirror. Given that and the cold, I am probably going to spend this weekend mostly indoors, maybe brushing up on some networking stuff I’ve long since forgotten… but I am already feeling stir crazy and have a few errands I want to run. I hope your cooking and cleaning goes well!