Failed?
Lift yourself up, or live there.
You know the work you need to do, be it physical, mental, emotional or spiritual, etc. So do it. Do the work.
The only bitterness in failure comes from not having the guts to get back up again.
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.
Have them sort change, and eventually to count it. It teaches them to gather things that are alike, it's an introduction to money and it occupies them for 15 minutes! Just make sure they're old enough to be past the point of putting coins in their mouth.
Check out from the library or Amazon: “My First Money Book: A Guide for Parents and Children to Saving, Spending, Sharing, and Investing Your Money” by Reggie Nelson
Start saving money early. Save as much as you can.
There are plenty of things worth spending your money on, but be mindful about your money - Don’t p*ss it away.
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!
Check out the Jesuit Volunteer Corp. A short but deeply meaningful immersion into service, faith in action, selflessness and living on a lot less than you think you need.
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.
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!