Rick, glad you checked in! I understand what you mean by knowing when work is enough. I retired at 66 (now 71) and don't miss working at all. Sorry to hear about your friend.
Itchy and FBL, I spent a lot of time during the last 3 years of my mother's life with her. I was with her when she stopped breathing. That experience (very peaceful) helped to shape my feelings about death ... BUT ... as I get older, I'm finding some changes in my perspective. I've had a number of nasty physical problems over the years and was told twice that I had at most 5 years to live. At this point in my life I am noticing myself slowing down and other signs of aging. In addition, I'm finding myself "not ready" to think about letting go yet - especially as I'm noticing some troubling symptoms. I guess there is still a difference in contemplating from afar Vs facing something more imminent. It's not so much a fear of death as that I'd like to live some years longer.