Thank you, definitely feel a lot more relieved after reading this. Actually, this is pretty much what my plan was while I was convincing myself that I should leave my job, and it made enough sense to do so at the time. As for the money, it was a combination of living like I had no money, having a really good CPA to manage my funds (and getting lucky after the 2008 crash), and receiving a large amount of company stock options that fortunately did very well over time. I also was fortunate enough to have my college paid for, and so I have never been in a debt situation. Also, the company I worked for matched 10% into a 401k, and I converted the mutual fund stock into company stock, and just got lucky that we did well. On top of it all, I was paid well for what I was doing. Counting all the benefits, it wasn't uncommon for someone to gross 200k+ in a low profile leadership position. Thanks again, this is all great advice.