I got severely mixed messages when I was young as my mother and father were polar opposites when it came to money. My father's parents went through the Great Depression and it made a huge impact on them. Woe to the person who took more food than they could eat on Thanksgiving (or any other time). My grandfather on that side died when I was still quite young. I knew he had owned a service station and that after that my grandma moved into a small 1 bedroom apartment. My father was extremely frugal - to the point that both my sister and I thought we were poor.
My mother grew up with house where her dad was a doctor and her mom never needed to work. They had a nice house and a second, vacation house. They were not nearly as frugal.
This lead to a lot of fighting over money between my parents and a sporadic financial education for my sister and me. My dad was very strict about how and when we could earn and spend money. My mother was just the opposite and argued that we should get at least some allowance without having to do chores. Neither really talked to me about money or finances other than vague 'always save' messages from my dad. All I knew is that we seemed to live in a nice house in a nice area but that it was filled with 'old' cars and hand-me-down-furniture. (They still have a couch that is older than they are and most of the rest is older than I am)
In college I got into a little bit of financial problems with my first credit card. Nothing big, just something I knew my father would not approve of but still not putting all the pieces together as to why. I was lucky enough to know to start saving into a 401(k) at my earliest opportunity simply because I knew, in some way, it was good and expected.
It wasn't until about 5 years ago that I really started putting all the puzzle pieces together. Some was driven from a dislike of the daily grind and working for others (If I am not INTJ then we at least have much in common) and a desire to exit as soon as possible. Some was from the general lessons learned from my father. Some was from the realization that my GP on my father's side ended up leaving an inheritance for their children while the Doctor on my mother's side (who I thought lived a much better life) left unpaid and hidden debts.
My mom would spend too freely but my dad would be so LBYM that I don't think he'd ever have any fun in life but now they provide a good balance for eachother.
As for me - this dichotomy is something I struggle with internally from time to time. Hopefully I am able to bring a good balance of savings and enjoyment to my family
While not relayed in the best way I am very thankful that my parents imparted their wisdom and knowledge to my and realize that not everyone is so lucky.
For anyone else reading this I would strongly encourage a more open discourse about money with your children and the reasons behind your financial decisions