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This post is the first of four stories about my experiences snooping on my kids and their online behavior over a period of years. Part two is here, part three is here and the final instalment is here.

This isn’t an easy thing to admit, but I felt a secret twinge of shame when I was reading the recent leaks about the National Security Agency’s surveillance program — the one that allows them to index all the phone calls of suspected threats, scoop up emails and other internet traffic, and even reportedly listen in on real-time voice and text chats. Why? Because I have either used or tried to use similar types of tools (on a much smaller scale, obviously) to snoop on, creep, stalk and otherwise digitally eavesdrop on the behavior of my children over the past decade or so.

While the tools may have changed over the years, and the websites and mobile apps and social networks they used have also evolved — from simple instant messaging and gaming through virtual worlds like Habbo Hotel and Club Penguin, all the way to Instagram, Snapchat and Tumblr — the ethical and social dilemma remains the same for many parents I think.

The NSA and its defenders have argued that what the agency does is justified — even though it may technically be against the Fourth Amendment — because it allows them to identify potential terrorist threats to the U.S. I made a similar argument to myself about the surreptitious monitoring of my daughters’ online activity: namely, that by doing so, I was helping to identify potential threats to them in the form of drug abuse, poor relationship decisions and other hazards of teenage life. Was I right to do so? To be honest, I’m not sure.

Invasion of privacy or parental right?

I do know one thing: when I casually mentioned to a friend and fellow parent several years ago that I was spying on my then-teenaged daughter while she was on the internet — capturing instant messaging logs, reading emails, even at one point using “keystroke logging” software to track what she typed — my friend was not supportive at all. Instead, she was horrified. How could I do this, she asked, when it was such an invasion of my childrens’ privacy?

At the time, I made the same argument that legions of parents before me have probably made, which is that my children really have no expectation of privacy while they are under my roof. In a sense, I figured they were subject to my laws rather than those of the Constitution — within reason, of course — and if I believed that invading their privacy was what was required in order to keep them safe, then I figured I should be entitled to engage in whatever behavior I saw fit. Shouldn’t I?

The hard part about all this, however, is that there’s a lot more involved than just reading your child’s diary or picking up the extension in the living room to try and eavesdrop on a call they are making from the basement. Although I have stopped snooping on my three daughters — since the oldest is now 24, our middle child is 19 and the youngest is almost 16 — I expect that there is so much technology out there that will allow you to track their every click and status update that you could (as I did) find yourself getting sucked far deeper into monitoring than you ever intended to go.

When I look back at it now, after almost a decade since I first began monitoring their online activity, I can see a number of lessons, some of which are more obvious than others. And I can see how in some ways it was a mistake, but in other ways it showed me things about my children — worthwhile, valuable things — that I would never have learned otherwise. And what’s also interesting is how different all three have been in a number of ways: in their use cases for the internet, in the technologies they chose, and in how all that affected my own approach to eavesdropping on them.

Keystroke capture meets teenager

My interest in all this got triggered in the early 2000’s, when I decided to do a review of some software that allowed anyone with access to a computer to capture the keystrokes of a user and store them in a file for viewing later. The software was targeted at employers, but parents were also a potential market — as an alternative to earlier “gatekeeping” software such as Net Nanny, which could be used to block certain websites from young children.

At the time, my oldest daughter — who was then about 13 — had been spending a lot of time talking with friends using Microsoft’s Instant Messenger, and I thought the software would allow me to eavesdrop a little bit on her conversations while also reviewing the software. I installed it as directed (it was just a driver that loaded before the keyboard driver, and stored all the information sent via the keys) and soon I was reading all of my daughter’s chat conversations.

For the most part, this was incredibly boring, I’m happy to say. Our daughter wasn’t the kind of troubled child who cried out for internet monitoring, so there was nothing outlandish like plans to meet up with some 35-year-old in Detroit. There was a lot of talk about boys and homework, and TV shows or books she liked. There wasn’t even any sign of “cyber-bullying,” which had become a big topic of conversation in the media, and which a niece of mine had been subjected to during her teenage years (another reason I was curious to try out the software).

A permanent loss of trust?

The only thing remotely interesting that turned up was a conversation about smoking pot one night at a friend’s party. Since 13 seemed a little young to be encouraging that kind of behavior, my wife and I had a little chat with our daughter about the wisdom of that kind of activity — without telling her how we found out about it — and that was pretty much the end of it. Eventually, I stopped looking at the emailed chat logs that the software forwarded me (it would send them based on certain word triggers as well) and went back to not paying much attention to what my daughter did online.

After the discussion with my friend and fellow parent who was shocked about my invasion of our daughter’s privacy, I did tell our kids that we had ways of looking over their shoulders online (without going into too much detail) and that we wouldn’t hesitate to use these powers if necessary. Better to be vague, I thought, so that they wouldn’t know what we were capable of — another echo of the NSA’s approach.

Obviously, my daughters’ emotional turmoil and fondness for certain bands isn’t even remotely comparable to the dangers of terrorism, but the parallels with what the NSA does (and what American citizens allow it to do in their name) still seem pretty strong to me. I believed that what I was doing was justified because I wanted to protect my daughters from themselves — but in the end, I decided that the loss of trust was actually much worse than anything I was theoretically saving them from. Is there a lesson for the NSA in there?

Thursday: My surveillance program continues with our middle daughter, and I discover something unexpected about her.

Images courtesy of Shutterstock / Lightspring and Shutterstock / Denis Vrublevski