Crisi, I think your end of life goals sound wonderful. It's great that you have enough money to live comfortably and that you want to help future generations with your money.
Here's my example: I may or may not end my life with millions. Right now I'm in the position of paying off the last of my and DH's school debt and a trip to
Disneyland and Hollywood that I took my dying mother on - I couldn't afford it in the slightest and went on credit. It was her dream trip. I own my little car and have no other debts.
I have always been financially responsible, though far from wealthy! I put myself through two degrees working 2 or 3 jobs at a time in addition to full time classes to come out with as little debt as possible. Now I'm working part time in order to better care from my mum who I moved in with when she got her cancer diagnosis last June. Between DH and I we're managing and able to put about $2k a month to the debts - we'll be debt free in a few months!
So why did I "waste" money on an $800 bag?? Well, to be fair, it was on sale for $600...

Each week I take $5 for myself, in cash, and put it in a jar. Along with some odd change and birthday and Christmas gifts it adds up. When I have a few hundred dollars I buy myself something I wouldn't otherwise consider. I have a beautiful pair of red bottomed heels and I carry a gorgeous purse. I buy something beautiful maybe once every two or three years. It's something just for me. DH has adopted a similar "splurge" savings.
As I said, we're on the right track, but may never have millions to leave behind. But that doesn't mean we won't make a difference. After my mum passes, we're going to South Africa. DH will complete his post doctoral studies and I'll be volunteering with a government organization as a professional volunteer. I'll be training other people as teachers to bring education to some of the regions and villages that otherwise would never have access to a teacher. Will I be paid a lot for those two years of work? Nope! But in way many people will never experience, I'll be making a difference.
People may want to judge me by my handbag, and for the most part I don't care, but I hope you can agree from my brief summary of my life and they would be quite wrong. It just goes to show that judgment in either direction is rather pointless.
P.S. Next big purchase, probably in the fall, is jeans! For $200. Maybe I should go to the other thread to defend myself...