Ryan, I have watched your pendulum swing widely from one extreme to the other. Here is my take as a 50-something dude with a few years into the game:

(1) Most jobs are "just a job" and expecting too much more from them will lead to disillusionment.

(2) Not getting paid "enough" in your job will lead to real frustration, and is only ok for the 1% who are MASSIVELY driven by some calling. For the rest of us, having "enough" for your family is really key. (notice I quote the word "enough" because I see very widely divergent views on how much is enough, so one way to have enough is to want less. (within reason based on where you live)

(3) even though most jobs are "just a job" it does not mean that all jobs are equal. Many "its just a job" careers still feature significant (a) learning, growth, and challenge. No one wants to not be going somewhere, so it is important that there is some kind of path that means at least a bit to you. Also (b) it needs to be a little bit fun and not terribly painful too often. finally (c) you need to have some purpose you can identify with. ok so it is an accountant, but it is for a firm that delivers clean energy, or helps with a product that people love, etc.

Do swing the pendulum so far over that you focus on pay with out a little bit of A, B, and C. You will burn out of that job faster than you did out of teaching! money wont save you.

(but notice in A, B, and C, I *never* said passion... my pendulum is in the middle ;-) )