George Orwell was right, of course, but he was twenty-five years too early. And twenty-five years too old.

As much as any civil libertarian feels put upon by the encroaching, omnipresent surveillance of the state, far worse off are their kids. Children — free of any such trivialities as Constitutional privacy protection — are monitored and cataloged and ear-tagged in ways that their parents can’t even imagine, and very often happily participate in. It’s all in their best interest, of course, the saying goes. But the implications of encasing our children in the physical and emotional bubble-wrap of good intentions are both profound and vastly under-appreciated. It’s not a new idea that kids today are coddled by perpetually terrified parents, but the extent of the coddling goes well beyond the home, into nearly every institution that makes up a child’s world.

An example: the other day, I dropped my kids off at their school late — Daddy needs his rest, dammit, and sometimes dawn comes too early — and by the time I got to work, I had this e-mail waiting for me:

Creeeeeeeepy. Creepier still, later in the day I got a phone call from a robot — a robot, operated without a hint of irony — that informed me of the same thing. My wife got the mail and call, too. And the record of this transgression — and the record of the notification of the record — sits, still, in the bowels of the Ministry of Education. Message sent and received: You just try skipping class, little mister. You just try. We’re watching you.

My children are now 11, nine and eight, and are coming into the prime years of adolescent mischief making. But in the age of computers and cameras and databases and twelve-foot-high fences and involuntary geolocation reporting and home drug testing kits and thermal imaging and full-body X-rays and God knows what else, is it even worth bothering? Is it even worth trying to bother?

I was never much of a teen-age troublemaker, and the risk aversion born in that time has followed me my whole life. Once, in junior high, I tried to forge my mother’s signature on an absence excuse, and the repercussions of that act — laughably minor from the safe distance of a few decades — left me with a disinclination towards anything that might cause someone in authority to give me a stern look. It hasn’t been a wholly bad thing, my adult timidity, but I can feel it hanging on my shirt tail any time I get anywhere close to the edge of what’s expected of me. It may be irrational, but it’s built in.

So, as part of the effort to give my kids neuroses entirely separate from my own, I want them to risk, to dare, to push boundaries, to test waters, to be pains in the ass every once in a while. Being late to class because your dad couldn’t drag himself out of bed in the morning doesn’t exactly pin the rebel-o-meter, but if that innocent, involuntary transgression brought down the full weight of the school’s monitoring system, gad, who’s going to even try cutting a class?

What’s important, and missing, is context. There’s no room for subtlety in a system designed for everybody.

When I was fourteen, some friends and I stumbled across a waterlogged copy of Playboy under a bush on the walk home from school, and — oh, my God — it was awesome. My kids, via the computer we have sitting out in the family room, have access to that very same 1982 issue. And every issue since. And every issue of every other adult magazine since. And endless, infinite terabytes of violent, degrading, revolting hard-core porn as well.

Do I shut down the computer? Do I log every mouse click? Do I worm my way into the very private world of their coming of age, with the best of intentions to protect them from all the filth that the world will eventually vomit up at their feet?

Of course not. They’re going to be teenage boys soon, and looking at naughty pictures is something they’re going to want to do, something they should do. News flash: Boys like boobs. And good for them — I’m a fan myself. I’ll watch, from a distance, as they explore their world. If they go too far, if they end up over the edge instead of at it, I’ll pull them back, of course, but not before. When and how depends on the context — I can’t tell you where the line is because we’re not there yet. But I do know it’s not going to be something the school district — or the church or my in-laws or any of the other tut-tutting, contextless, rule-bound institutions that teem and thrash like spawning fish — would approve of.

The goal is not to prevent them from making mistakes, but to allow them to. Risk assessment, trust development, value determination, responsibility, self-direction — all of these very important skills grow out of the opportunity to explore, to experiment, to make mistakes and correct them. Short circuit their opportunity to screw up and you’ve destroyed a chance for them to learn something new, about themselves and about how the machine works.

This is a terrified little world we’ve built for ourselves, and we’re far too eager to pass it on to our children, ringing bells and slamming doors the instant they step off the bright yellow line painted on the floor. But I’m going to try like hell to do the opposite: Open the cells! Take off the chains! Set them free!

And if they don’t come back, then you hunt them down and lock them up.