This was very much how my father felt about his own father. As I was growing up, my dad pointed out how my grandfather hadn't really lived his life, hadn't taken those chances, and even though he still at that point had a chance to live a fuller life, it was like he chose not to.
It's sad when the people who came before us miss out on the things they could have done, but it's worse if we don't take the opportunity to learn from their actions and inactions.