I had very high earnings coming out of graduate school but then proceeded to do a couple more entrepreneurial things and in my last position, I took a pay cut in order to change industries completely. My social circle is very affluent and I constantly feel poor in contrast to my friends and acquaintances (I live in Boston around a lot of highly educated, white-collar professional types). I'm not starving or anywhere near insolvency but I feel really jealous of my friends' relative financial security rather than mine. I pursued my decisions with a clear-eyed view of the risks but I am now in my mid-forties and regretting it a bit. Nothing much to do about it all, I suppose, but having a pensive Sunday.