For me? As an answer to #1, I would say:
- Having a life partner that shared my financial "dream", which not only saving/investing for retirement, but also generally agreeing to a LBYM lifestyle.
- A personal goal (driven by my late father). He didn't give a damn about his family, but only to satisfy (through whatever means) his personal "desires". I strove to do better. I found that taking care of my family drove me to ensure our financial independance, which in turn lead to a retirement at an earlier age than most. Not ER, but at age 59, better than most of the folks I wor*ed with.
#2?
Sorry to say that I have no regrets as pertaining to retirement preperation. Even though I've been retired only four years, I have no second thoughts nor to I think I could have done anything "better" (yes, I'm lucky).