I LOVED this post! It fills me with a good, warm feeling to see someone as intelligent as Steve write like this. I've had these exact same thoughts for many years, but I thought it was just me, and that I was not "normal". Back then, I couldn't see other possibilities than having a job anyway. I didn't know better.
Now I know, and Steve's the reason. I spent 3-4 months just reading his old posts before joining this forum
I'm glad I joined, as I've also discovered more good personal development websites now!
Perhaps the truth is that you can switch careers as much as you’d like — and that those who’d judge you harshly for it are probably just pissed that you’re reminding them of how stuck they are. Do they really have your best interest at heart… or are they trying to enlist your support in assuaging their own self-doubt and insecurity?