Children need to know not only what challenges they will face, but how to rise to them.

Gen Xers often joke—on Facebook, naturally—about how much trouble we would have wreaked if our youthful stupid mistakes had gone viral. But what could have mortified us 20 years ago we handled by destroying photos and negatives. (Photo burning was a staple of late 90’s bachelorette parties.)

Contrast that with the Dropbox porn story coming out of Virginia, in which two boys put a bunch of nude or semi-nude photos of female fellow students on Dropbox and passed around the password. A little flash nudity has been a staple of Truth or Dare games for generations. What’s new is the capture and distribution capability—and the children unprepared for its consequences. Today we have no simple fix to save these girls from crisis or, perhaps, the boys from incarnation.

After one of these events, a chorus begins to ask, “Where were the parents?” But I often wonder about the teens. How could they possibly think these acts were a good idea? Or put another way, for how long do we think parental supervision is the answer?

I don’t ask to assign blame, but to focus on the problem at hand. Controlling the Internet isn’t an option—not legally, not logistically. Sufficient supervision isn’t possible. (I have tried every Internet filter variation, including prohibition. They all have exploitable flaws.) We will have to teach children to use judgment.

But modern parents don’t like judgment. We like control. Some parents brave culture for their children, clearing all obstacles. Other parents set all the rules and boundaries for their children. In both cases, parents substitute their judgment for their children’s and leave each of them vulnerable to life.

Modern parents don’t like judgment. We like control.

Stories of how well children of helicopter parents fare in the adult world are reaching legend. Some homeschoolers get heartache when their carefully pruned broods rebel. Similarly, many Christian denominations are puzzled by the trend of the young leaving the church, with only a fraction returning later and usually to more traditional Catholic or Anglican traditions.

Jessica Misener illustrates this (unintentionally) in her account of her rejection of faith. It is a story about faith, but the doubts involved could easily apply to most anything else:

Anyone can be a secular student of religion, examining the Bible as a historical work of literature in the same way one would analyze Shakespeare or the Euthyphro. This scholarly approach to the biblical text was the one taught to me at Yale University. Still, I entered my program with both feet planted in my evangelical sandbox. You can study the Bible like any other book but still keep your faith, I told myself. If I really believe that this book is true, then it should hold up to even the most rigorous historical-critical scrutiny. ….[B]ut something else materialized: a swelling doubt about the faith I’d set out to preserve, which hinged almost solely on believing the Bible to be the literal, inspired word of God. … This was something the evangelical students in my program at Yale talked about often: the behemoth of doubt that sets in as your airtight hermeneutic of scripture is drained from the bottom. Christians from other traditions didn’t have it so bad. Catholics, for example, could fall in the same academic dunk tank and emerge with the same doubts about scripture, but they could still lean on other things their denomination held sacred, like the Catechism, papal infallibility, and the Sacraments. We evangelicals, with our infallible view of scripture ripped from our hands, were left gasping for air.

Misener’s foundational Christian education had very little substance, just rules and joyful praise. Her church didn’t prepare her for the intellectual arguments that the world would bring. Heck, her church seems to have denied there were any intellectual arguments to be had. And then, when ambushed by those arguments at Yale, her former teachers lost their credibility in her eyes for what they didn’t teach her, and unless Yale had some Alister McGrath types on the syllabus or covered the logic of Leff’s “Memorandum from the Devil” or C.S. Lewis, she had nothing with which to counter. It should surprise no one that she ended up adrift. If she ever sorts it out, she will likely be quite put out about her lonely decade in the wilderness. (I certainly was.)

So what should parents do?

Parents need to tamp down on their reflex to control their children’s environment. We can only achieve control in privileged circumstances up to about 36 months. After that, attempts at complete control merely substitute the parent’s judgment for the child’s and start to set the child up for future gasping for air.

My husband and I teach our children by exposing them to culture, temptation, and counterarguments. The tactic that has brought me the most disapproving pursed lips has probably worked the best: Real news. Other mothers don’t approve, to the extent that my son’s teacher had to sort out a separate table for the four children who talked real events at school. We don’t just leave them to explore on their own. As a housewife, I do the day-to-day practical prep and instruction, so I influence their exploration before it begins.

For instance, I got my 10-year-old son a subscription to The Transom. This prompted a NSFW labeling panic from Ben Domenench one evening when I mentioned in an email that my son was sending me Transom links. I waved him off, as NSFW would be like a”‘wet paint” sign to a boy, and then explained.

When I wanted our children to learn to snack well, I didn’t set a bunch of rules or allow for a free for all access to the fridge and pantry. I strategically made good snacks, like apples, available by displaying them in an appealing way at easily accessible locations. I influenced their choices without telling them what to do and they made a habit of healthy snacking. I now buy apples by the bushel.

The Transom is apples.

Ben writes the newsletter with a reasoned tone and no hiding of counterarguments, so my son gets good reasoning as a model. And I read it. My husband reads it. We can easily stay ahead of our son’s thought process when he comes to us with questions and we can help him understand the facts or reasons better. But my son is doing the initial reasoning himself. By the time he stops coming to us for guidance—in that delightful way of all-knowing teenagers—he will have some critical reasoning habits of his own. That is a far better safeguard than relying on parental supervision of 16-year-olds.

There aren’t age milestones for this. You use what you know about each kid and what topics and mediums might get their critical reasoning skills simmering. My eldest daughter is 8 and just now starting to show curiosity and ability for some of the conversations we have with her brother. I think she will start a little earlier than her brother and that her apples will be stories.

But we must teach children to eat their apples on their own. (Yes, I see the irony of this analogy to apples. But it is what I told Ben, and apples are more universally liked than the bowl of cherries currently on my counter. Besides, some scholars think the Forbidden Fruit was a pomegranate.)

Children need to know not only what challenges they will face, but how to rise to them. We cannot teach this by merely telling them what to do or modeling what needs to be done. They need to try their mettle. We need to expose them to culture while guiding them with lessons in critical reasoning, slowly backing off to let them be tested, in increasing difficulty.

We must teach them to discern right from wrong, on their own, and have the fortitude to act upon it. Otherwise, the kids are only one peer-pressure fold from swift and lasting consequences.