"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.
Start a yearly “review” right before school year. Raise allowance as appropriate. If they want more money, they’ll have to take on more responsibilities.
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.
Work on developing a “no shortcuts” mode. Looking for a faster/easier/bare-minimum option isn’t always bad. People get paid a lot of money for creating efficacy. But there are times when that approach is wrong. Anything you want to grow from (relationships, school, work, wealth, health, knowledge, etc.) those things deserve your full effort, focus and dedication. Play. Definitely play! But don’t f*ck around.
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.
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.
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
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!)
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.