I also left. Productivity shot up and office supplies theft plummeted.

> I left.

You know, this is one thing I need to learn: when to bail out on a situation that's beyond repair. I have a bit of a mental block about quitting without anything lined up, and job searching is just annoying enough for me to not want to do it without the incentive of needing to replace a paycheck. But, there are definitely a couple times in my career that I should have left long before I did, and I believe things would have worked out much better for me if I had.

I'm interested on anyone's thoughts on "when it's time to leave."

It's a good question and probably depends more on your personal circumstances than the job. I have often felt like leaving when I didn't agree with some core aspect of my org (product, culture) but I try to be pragmatic and accept that I am paid to be there and although globally I want to do something more fulfilling, it is better to lo cally tough it out and wait until I'm well positioned to make the next move. So maybe one thought is to ask yourself what is missing for you to be able to make a move, and try and work on that.

Incidentally, at my last job, I realized that what I was lacking to land the next job I wanted was also what I was lacking to be successful in my then current job. In the end I made progress towards remedying that, moved to a new job but also left on a high note as a result of my personal improvement.

It depends on what you value and what your drives are. But to give you a bit more tangible advice. When you are asking your self "Is it time to leave?" a couple of days in a row, it's probably time to leave. And don't fear leaving, the amount of growth and experience it brings you is mostly already worth it.

What Dev resources (blogs/books/etc) could you recommend that could help better explain this mode of thinking and how to turn it into a practical and practicable methodology of working?

I'll suggest Goleman's Emotional Intelligence (for empathy) and Pirsig's Art of Motorcycle Maintenance (for quality and values).

Massive upvote for Pirsig. I did not understand Apple until reading this book. I think Tesla maybe our contemporary equivalent.

Can you please explain in a paragraph what this book made you understand about Apple?

Granted it's been about 10 years since I read it...

In addition to what electrondood said. It helped me understand that there are some people who just want their technology to work. Not to understand it's qualities. John Sutherland (the character with the BMW). Many Apple users are like that. They want the defaults to work for them. They want to remain clueless and it "just works" ...

And I think getting to the end of the book, and seeing Pirsig descend into a pretty dark place in understanding quality being undefinable in any actionable way, I guess sometimes it's easier to just let go, and not understand something. A lot of times, understanding just makes us more miserable. Fantastic book, read it as a teenager and it deeply affected me.

A gross paraphrase I got was "I cant define quality, but I know it when I see it".

That's a great one! Something that can be validated yet not easily calculated. Kind of like hashing!

It's basically an exploration of the elusive quality of Quality, which Apple is obsessive about.