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.
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.
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.
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.
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
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 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.
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.
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.
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.
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.
There’s always a temptation to throw money at your problem. But remember there’s nothing you can buy that will make up for what is really needed. And the stuff that accumulates while you try to fix the problem just ends up being a problem on its own.