Take the family on periodic “spending fasts.”
As an exercise, go a day, a weekend or a week without spending any money. Make due with what you have.
Encourage participation. Tie in spending fasts with holidays, lent or in support of a cause.
It’s fine, great, to be thrifty. But please don’t be cheap. Hard-earned money should neither be squandered or hoarded. Enjoy your success! But save more than you’re comfortable with. It’s like my running coach used to say: Keep going until you feel like you’re gonna poop your pants, then push yourself to do another mile. Point is, it should hurt a little.
Practice “going without.” Talk about how nobody gets what they want all the time. We should learn how to just choose to go without something we want. Get them in on the discussion and pick something every day to do without.
"Watch the pennies and the dollars will take care of themselves." - Ben Franklin
This works with money and with other areas: Be faithful in the little things and the bigger things will take care of themselves. For example, if you don't get comfortable with telling little lies then you'll never tell big lies.
Beware that when you’re first exposed to a new thing: a car, a college tour, house, etc. you will feel AMAZING and totally seduced by the shiny newness. Be cool. Remember that glitters is not gold. Things don’t need to be perfect and even if the house is it doesn’t mean life will be.
Don’t have a clue? (Relationships / career / character, etc.) The solutions can be found in books. READ! Novels, biographies, history, religion, humor, politics, finance, sports, and whatever sparks your interests at the moment!) You’ll learn about the world, and you’ll learn about yourself. READ!!!! (or listen!)
IMPORTANT: If you borrow money from someone pay it back as soon as possible. In full. If you borrow an item, return it in excellent condition. I’d say if you borrow a car, return it with a full tank of gas but hopefully by the time you’re driving there won’t be any combustible engines. So return it fully charged!
I once asked my mom if my grandmother (her mother in law) was rich. Her reply: “No, but she likes to think she is.” I think she meant my grandmother spent money like she had plenty of it when she really did not. Can relate. I hope you do better!