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.

“AAAAAaaaaaagh!”

“Please calm down. Breathe deeply. Anxiety is a normal part of the temporal displacement field. It will pass quickly. OK. OK? OK. Now: Hello. I am you, from the year 2010, two decades in the future.”

“Aaaaaaaagh!”

“I said, calm down. The panic will pass.”

“Calm down? Calm down? You’re fat! And bald! I’m going to be fat and bald!”

“Hold up there, Sparky. You’re already fat. And will it help with the bald thing if I assure you that you’re, um, romantically involved on a regular basis?”

“But…”

“Regular basis.”

“Yeah, OK, fair trade.”

“I’ve come to the past to tell you two things.”

“Other than the bald thing?”

“Yes. Other than the bald thing.”

“Is it about nuclear war? Because radiation would explain why all your hair has fallen out.”

“In 2010, Apple will introduce a new computer, called the ‘iPad.’”

“Hee!”

“You’re thinking of a sanitary napkin joke, aren’t you?”

“Hee!”

“Would you like me to describe this computer to you?”

“Is Apple even still around? Microsoft just launched Windows 3.0 and—”

“It’s about the size of a piece of paper, half an inch thick and weighs a pound an a half. It has 64GB of storage, can play tens of thousands of songs and can display everything from photos to high-quality video. It has a touch-sensitive screen, is completely wireless and can connect to the Internet from just about anywhere.”

“Aaaaaagh!”

“Pretty cool, huh?”

“Holy crap! Oh, my God! Do you guys have, like, flying cars, too? Did aliens come and give you this technology? That means I can get USENET anywhere.”

“Um. Yeah. The Internet expands a bit from USENET, by the way.”

“Gopher?”

“Yeah. Gopher.”

“Oh, man. Can I see it? Do you have one?”

“Well, no, I don’t have one, because it won’t come out for another two months. But, here, I’ve got a smaller one that can make phone calls, too.”

“Aaaaaaagh! Oh, my God. This is so cool! All this, and I’m getting laid, too? People in the future must be so happy!”

“Actually, no. People are sort of disappointed.”

“What? How is that even possible?”

“That brings me to the second thing I want to tell you. In 2008, America elects a black man President.”

“What? Really? Like Morgan Freeman in ‘Deep Impact’?”

“No, you anachronistic goober. That movie doesn’t even come out until 1998.”

“So, he’s like Disraeli or Thatcher, right? Only Nixon can go to China? He’s really conservative? Please tell me you don’t elect Alan Keyes President.”

“No, no. His name is Barack Hussein Obama.”

“OK, now you’re just screwing with me.”

“No. Totally serious. He’s liberal, intelligent, deliberative, pretty much everything the country needs after Bush.”

“Bush? But Bush is President now. Please don’t tell me that he’s still around in 2008!”

“Oh, no. You’ve got the good Bush. The other one is who Obama is cleaning up after.”

“Wow! That’s awesome. That’s wonderful to hear. People must be really— Oh. You’re going to do that thing again, aren’t you?”

“Yes, I am. A lot of his supporters are disappointed.”

“With what? A liberal black guy got elected President!”

“And in his first year, he prevented a second Great Depression, has stopped torture as official policy, is winding down an unnecessary war, has dramatically opened up the transparency of government and has gone a good way towards restoring America’s place in the world.”

“And people are disappointed?”

“They want more.”

“Like the people disappointed with the computer?”

“Yes.”

“So people in 2010 are dicks?”

“They’re cynics.”

“Oh, please. I’m a cynic, and all this stuff sounds incredibly great.”

“That’s why I wanted to talk to you, 1990 me. Your cynicism is important, even vital. God knows, there are times when it will seem like bunnies-and-rainbows optimism given what actually happens. Things get really, really bad for a while, and no amount of cynicism seems like enough.

“But I also wanted to make sure that there are some things that are, in fact, awesome. The world’s been through a hell of a lot, and I’m not sure I trust my own eyes anymore. I don’t agree with every one of Obama’s policies and I doubt that I’ll buy an iPad, but does that make their existence any less amazing? What would the bright-eyed, long-haired, involuntarily celibate version of myself from two decades ago think?”

“I think it’s amazing. All of it. And I’m even ignoring the fact that you can apparently time-travel.”

“Good. That’s good to know. I look at some of the stuff that’s going on, what we can do and what we’ve done, and I want to be astonished. But some small, mean, broken part of me thinks it will all go to hell, that it’s a trap.”

“Wow. You really are cynical, aren’t you? It all looks great to me. Magic. The future! Man.”

“OK. Thanks. Oh, and two more things.”

“Yeah?”

“Don’t ever used the words ‘Meh’ or ‘Fail.’”

“OK.”

“And in a couple of years, when you’re deciding if you want to go on a blind date with someone’s lawyer friend, do it.”

“Seriously?”

“Talk about awesome.”