I usually give my Rhode Island sailing companions the same advice about reefing that I do about voting: early and often. Unfortunately though I am good at dispensing said advice I am bad about following it. Countless times we end up grabbing a mooring after a hard sail and saying to ourselves, "pass the martini pitcher. Boy we should have reefed."
I remember once I was sailing a 29' sloop down the east passage of Narragansett Bay to Newport. I had a friend onboard who had been sailing before, and a girl friend of his who had never been. We started heeling quite a bit and took some water over the rail. She asked me "is this OK?" I replied, "Gee, I don't know. It's never done this before." That was a mistake