"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 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.
Start “home economics” school with them. Laundry, cleaning, cooking, how to change a diaper, comfort a baby, soothe a toddler, what's involved in caring for pets, budgeting for food, keeping track of maintenance schedules for humans, pets, cars and machines. Engage with guests, be a good host, etc. Know when and how to tell someone to GTFO of the house (racist or misogynistic speech, etc.) Every kid needs to learn the art and science of home management. Look for and point out examples in books and movies of good home science skills.
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.
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.
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.
Have a yearly “review” right before school year. Raise allowance as appropriate. If they want more money, they’ll have to take on more responsibilities.
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 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.
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!
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.