"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.
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.
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.
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.
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.
Misquoting someone here: “It’s not about getting everything you want, it’s about giving everything you have.” Stuff will never satisfy. Pouring yourself into something heart and soul will.
Set up automatic payments so they are initiated on your end, so that you send out money to the bill/ company you’re paying instead of giving them access to take money out of your account.
***Manners!! *** Etiquette is the secret sauce. Everyone appreciates being treated with respect. Etiquette is the art and science of respecting others. It’s timeless and universal. Customs change, hence the need for constant study, but respect is always the foundation. In summary: Be nice. Start with yourself. Study etiquette. It will help you in every single interaction you have, social, professional, financial, everything. Manners apply to every human, in every interaction, even on the hard days. Hence, the need for practice.
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.
Start saving for retirement with your very first paycheck. Put away the MAX, you’ll never miss it. If the company doesn’t offer 401k then we’ll open a Roth IRA.
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.