Just as you have built your online life over time, so will your child. Your understanding of the rewards and risks has expanded over time -- and you can't just expect your child to know everything from the start. That's why teaching children about life online and releasing the reins to give them more privacy is a process, not an instantaneous event.
Before you and your child even sets up that first email account, establish expectations. Talk about risks in online communication, as well as benefits. Be clear that your ability to monitor activity is a condition of access and that if your child demonstrates good choices and appropriate online etiquette, the monitoring will slowly diminish.
For example, some email services allow all incoming emails to be copied to another email address. As kids start to use email, this is an easy way to learn about what is coming in and from whom. And if you see something that shouldn't have made it through -- and given that 80% of email is spam, something might! -- you can intercept it before you're ready for that awkward conversation about little blue pills.
Allowing your child full privacy in Internet -- and life! -- matters is a process, and it depends on the child's relative development. What is okay for one child at 12 might not be okay for another child at 14 -- and you know your child best. For the younger child, daily monitoring of activities is very reasonable. For the older child who has proven responsibility, only an occasional check in may be necessary, if at all.
The releasing of the reins will be a subtle thing. After several months or longer online, you realize you forgot to check your child's activity for a day or two and it was okay can be a signal that it really is okay and you can pull back even a little more. But don't check out entirely.
If you see an issue during this letting go process, you can pull back the reins as necessary. Yes, you can, despite protests -- you are the parent! If, for example, your child's grades slide around the time you allow greater texting or social networking freedom, that could be your signal to pull back a bit and reestablish boundaries before trying again.
The ultimate goal is, of course, a child who grows into a well-adjusted young adult capable of managing the responsibilities of life, including online life. You don't want to be intrusive and violate privacy, but you do want to parent them though it.
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