Help Needed: “My 7-y.o. is Too Scared to Do Anything On His Own”

Hey Folks — I am putting this up in the hopes that we can help this mom and her son. As I told her in an email, even yours truly tends to worry when anything’s up with the kids, but fortunately, life is fluid and so are they.
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It also seems that being less than adventurous at age 7 today is almost a given. Yes, I want to change that — I think it’s a great age to start exploring. But he’s part of the world of modern 7-year-olds, and most of them are constantly supervised, so he may have absorbed the idea that anything less is “scary.” Just like the parents who need proof that their kids really are ready to walk to school or play on their own (they are!!), this boy may need to see it to believe it, too. 
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Finally, let me state here that Free-Range isn’t just about giving parents a break from constant interaction/supervision. It’s about making kids part of the world and excited about it, to boot! So he has to see an upside to this independence. 
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From what I’ve witnessed, chances are pretty great he’ll just grow out of this timid phase. But of course, readers, if you have some ideas, please share!- L.
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Dear Free-Range Kids: Help! My son is 7.  He is perfectly capable to be as Free-Range as I was at 7, but he won’t.  He is too afraid to go places alone.  I only just got him to cross a street by himself in the last year (so I haven’t been pushing him too hard, I don’t think).
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He refuses to go anywhere without a parent.  He won’t use the phone to call a friend and relies on me to arrange “playdates” for him (which I have now refused to do).  He won’t even knock on a friend’s door even if I am standing on the sidewalk.  He is shy, but even though I was shy at his age too, I was still able to do things!
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I would love for him to walk the 4 or 5 blocks it would take to get to the playground in our neighborhood and go play without me having to come and sit and “supervise.”   He keeps saying that when he is 13 ! he will do these things on his own!  He told me he wished he had parents like his friends, whose parents don’t let them go anywhere without them.
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He is an only child and people keep telling me this is why he is like this.  He is popular in school and well liked.  He isn’t outgoing, but he is normal/shy, and that is why this really bothers me.  I can’t stand another month+ of this.  What can I do to show him he CAN do things without me before he’s 13?!  How can I foster an independent spirit in him?  How do you make a kid Free-Range who refuses?

-Gina
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What happens when a mom is Free-Range and her boy isn’t?

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