Laura Rowley Money & Happiness

Medical advances can pose unique money and parenting dilemmas.

Take the recent breakthroughs in orthodontics: At the age of eight, my oldest daughter had an appliance installed to break a nighttime thumb-sucking habit that had aggravated her overbite and parted her front teeth like the Red Sea. (We'd exhausted all the old-fashioned methods of breaking the habit.)

A year later, she was fitted for a removable retainer that's already done wonders for her smile, and may allow her to avoid braces altogether.

Disciplinarian or Tyrant?

I invested in this process at her dentist's recommendation, although I suspect I had a subconscious desire to protect her from her mother's fate. There's nothing like a Bugs Bunny overbite, some acne, and caterpillar eyebrows to build character in those vulnerable middle-school years.

The treatment had already cost the equivalent of a weeklong vacation rental on the beach when she lost the retainer. I fumed and explained that orthodontia was a luxury, not a need, and then paid $200 to have a new one made. I told her if she misplaced it again, we would postpone the orthodontics until she was older. Then, the other night, she lost it again.

I railed about her irresponsibility and banned television for a day. (She'd set the retainer down somewhere while absorbed in Nickelodeon.)

After tearing apart the basement TV room in vain, I went to bed wondering whether to make good on my threat. Do I end the orthodontics and pick up when she's 12 and more responsible? Or had I overreacted? (Joan Crawford in Mommie Dearest came to mind: "I buy you beautiful dresses, and you treat them like they were some dishrag! No wire hangers, ever!")

Costly Mistakes

Much is written about how to develop good financial habits in kids. I've had readers share terrific ideas for teaching kids about saving and spending ("From Readers, the Best Ways to Raise Money-Smart Kids"). But it's a little trickier figuring out what to do when they make a costly mistake -- especially the same blunder more than once.

When I was a kid growing up on the south side of Chicago, there was a fairly professional gang of bicycle thieves who drove around in a truck, boldly swiping anything that wasn't chained up -- even from backyards. I recall a ride to the local pharmacy, where I breezed in to buy candy and was out in two minutes, figuring nobody could steal a bike that fast. I figured wrong.

I didn't have the opportunity to repeat the mistake, because with 11 kids in the family, replacing my stolen wheels wasn't a budgetary priority. I walked, or borrowed my siblings' bikes.

But what if you have the money? What if your kid has a fender bender, and despite your earnest lecture totals the car a few months later -- and then has no way to get to his job? Or say you give your teen a $100 clothing budget, and he blows it on a single pair of sneakers two seasons in a row?

Do you let them suffer the consequences -- lose the job, go through the school year a fashion reject -- when you have the cash in your wallet to solve the problem?

Bearing the Consequences

I can't help wondering if we set our kids up for bad long-term consequences when we bail them out from youthful financial carelessness. I've known a few parents over the years who were still subsidizing their 20-something, and even 30-something, children (or couldn't get them to move out of the house).

On the other hand, I worry that my daughter won't learn to be forgiving and generous with others if I'm not forgiving and generous with her.

Kevin McKinley, a Wisconsin certified financial planner and author of Make Your Kid a Millionaire: 11 Easy Ways Anyone Can Secure a Child's Financial Future, suggests letting kids bear the consequences.

"If a teen totaled the car," he wrote me in an email, "I would first thank the heavens that he was OK -- then I would tell him that he should explore alternative transportation -- taxi, bus, bike, etc. Or make him pay for the increased cost of car insurance borne by a family with an accident-prone teenage driver.

"And I love the idea of a kid pimped out in $100 sneakers and second-rate clothing. If pricey shoes are a priority, he can demonstrate just how much by sacrificing his appearance from the ankles up."

In my case, McKinley suggests that ending the orthodontics would be self-defeating: "While it's understandable that you are upset, delaying treatment until she's older may end up costing you much more in time, and maybe more in pain and money," he writes.

"But you could help her understand the cost of her actions. She could pay for 20 percent of the replacement cost (a lot of money to a 9-year-old), or perform some tedious chore that she otherwise wouldn't have to do."

Perspective is Priceless

At minimum, parents should avoid my mistake, and wait until cooler heads prevail before spouting threats about what will happen if a child becomes a repeat offender. Researchers have found a phenomenon they call the "hot/cold empathy gap" that can lead to errors in predicting both feelings and behavior.

When people are in a "cold," or neutral, emotional state, they often have trouble imagining how they would feel or what they would do if they were in a "hot" state -- angry, hungry, or in pain. On the other hand, when we're experiencing a hot state, we have difficulty imagining that we will calm down at some point.

That explains why, feeling sheepish after my outburst, I got up at 2 in the morning and started searching the basement again for the lost retainer. I carefully shifted the furniture, disrupted the gerbil in his cage, waded through toys, and sorted the mountain of bemused-looking stuffed animals.

Just when I was about to give up, I looked down, and there it was -- two pieces of clear plastic and metal wires, nestled inside a doll's crib.

I realized I had lost sight of the big picture, and the next morning apologized to my daughter for overreacting. Labor Day is here, another summer has come and gone, and she no longer plays with the doll's crib. She'll be out of orthodontics, out of high school, and out of my home before I know it.

And maybe right now, in my neutral emotional state, I can't predict how I'll feel when that time comes. But my guess is that I'll ache for everything about her -- even her inability to hang onto a retainer.

When kids make mistakes, what's the appropriate response? When should we bail them out, and when should we let them suffer the consequences? Send your thoughts to laurarowley.column@yahoo.com.