It definitely must have hurt to look back and ask, "what else could I have done with that money?"
I used to be very bad at it as well and I realized some people who made considerably less money than I did were in a better situation than I was.
I was going to write something about this, as over the last years, people are talking more openly about personal money matters, which I think is a good thing. Now during the "down" times, it has taken a different tone - it feels a bit like people are trying to probe to see if others are struggling too.