Laura Rowley Money & Happiness

My readers have ample wisdom and experience to share on whether to bail kids out when they make the same money mistakes repeatedly, the subject of my last column ("To Bail or Not to Bail").

Here are the highlights:

When I was in high school, I had to buy my own first car with hard-earned money from my part-time, minimum-wage job. This was in stark contrast to one of my classmates, who didn't work (or get good grades, as I did) but was nevertheless rewarded with a new BMW.

My 20-year-old car lasted longer than two of his new BMWs, as I was very aware that if I broke it, there was not another one waiting for me. My classmate wrecked both of his cars, and then threw a tantrum when his dad wouldn't buy him a third.

Sure, it may have been traumatic to my classmate to have no car when he had previously been the coolest kid on campus, but he got over it. He also learned, though belatedly, the value of a dollar. Upon having to buy his own car, he opted for a small, used truck... and took care of it.

I would suggest that you view times like your [daughter's] retainer episode as teaching opportunities rather than trials. Perhaps her having to pay $40 of the replacement cost is just painful enough to make the point quite clear to a child of that age, whereas having to pay the full $200 would be unbearable. --Jonathan Kahn

Luxuries and Responsibilities

I consider myself an extremely responsible adult and have only my parents to blame. Despite this, between the ages of 5 and 12, I managed to lose my eyeglasses and/or my retainer at least two dozen times. I also lost many balls, bats, mitts, and other things I considered "prized possessions."

The glasses and retainers were always replaced, albeit not without some healthy browbeating from my parents. The other items were not, and it was my responsibility to find the money (or earn it through chores or other personal sacrifice) to get them back. The lesson I learned? Certainly it wasn't "good children never lose things." Rather, it was "life is full of both necessities and luxuries -- learn to distinguish one from the other." --Tom Preston

We have two kids, both grown. My wife and I expected at least one accident and one speeding ticket for each child. ... We told them that they had one freebie speeding ticket, but after that there would be dark consequences. It worked.

For us, as I'm sure for you, financial responsibility goes hand in hand with personal responsibility. Kids suffer from lack of experience and many parents are very judgmental about kids' mistakes, which are really nothing more than a lack of experience. What my wife and I tried to remind ourselves of during the adolescent crises was that we had no more experience being parents than our kids had being kids, and that getting heavy-handed might not be the best way. --Bill Klym

Nip It in the Bud

This spring, my 14-year-old son was waiting outside his class for his teacher to unlock the door. He had to use the restroom, and asked a friend to keep an eye on his backpack. When my son returned, the class was open but his friend hadn't taken my son's backpack inside and it was gone. It was found the next day, minus my son's iPod.

I wasn't happy with his friend, but ultimately felt that it was my son's responsibility. I offered to pay half the iPod replacement cost if his grades were up to snuff for the semester. Bottom line -- he ended up having to save all summer to pay the full cost of a new iPod (and ended up with one not as powerful as the stolen one).

The same son couldn't find his expensive geometry calculator at the end of last school year, so I told him he'd have to pay for half ($45) of his Algebra II calculator this school year. But if he still has the new calculator on the last day of school, he gets reimbursed for the $45.

Both fair responses? I think so. Will he learn his lesson(s)? That I don't know. But I can be pretty sure that if I'd bailed him out now with no consequences I'd still be doing it when he is 24. --B.L.C.

Leading by Example

I made mistakes so often as a kid that it's hard for me to recall how my parents specifically helped me out of each jam. (They were pretty creative folks.)

Usually, I had to somehow pay my own way out. They would put me on a payment plan of some sort, and when I would get to about 90 percent they would cancel the remainder on good faith. I am now a daddy with the means to pay for nearly anything I wish. I only hope I'm able to teach my girls the same fiscal responsibility I somehow acquired while also satisfying their ever-expanding material wishes, my desire to grant those wishes, and my own blue-blood Yankee frugality.

I think the larger point is that it's difficult to map a standard course, because each child/parent/family economic condition is different. Leading by example is the best way to ensure that your children act the way that you want them to. --Scott Kay

As a newly empty-nest parent of three great kids, I chuckled at your projected feelings of nostalgia at some future day when you look back as your child leaves home. I remember feeling this way also. The thing I didn't realize is that at the point of departure, they will be quasi-adults (old enough to cost a ton but too young to pay for it), and if you have done your parenting full-throttle, the feelings of nostalgia will be replaced by a welcome and hard-earned rest. --Jim Vetter