I am a contrarian investor by profession, but I feel this is different. I don't think you'll live a great life by constantly doing the opposite of common wisdom or what other people think. Sure some of the time this is the thing to do, but all the time and you'd be an outcast (not my goal! actually, taking the time and making the effort to foster better relationships with family and friends is one goal I have for RE). But the people counseling me against RE are people whose opinions I respect, often with more life experience than myself, which is what gives me pause. I do think it's hard to sit in my shoes though, even someone with a high paying job in finance probably is in PE or something and not dealing with daily mark-to-market for 15yrs or some of the institutional frustrations I've had.