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!
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.
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.
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.
"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 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.
Be discerning about your sources of information. Some red flags: Too good to be true. Get rich quick. Chosen race. Any race or group blamed for societal problems. Fear of change. Threats of real or metaphysical harm (I.e. $@!#%) or bribes with reward.
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.
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.