Yeesh, this morning I put my kid on New York City public transportation (the bus) for the first time. Being that I first started walking home in second grade, and was taking the subway in crack-era Baltimore by fifth grade, I'd spent much of this summer lobbying (successfully) for more independence. I thought I'd be pretty emotionless about the whole deal. I was wrong.
I didn't exactly go to tears, but it's very hard to let your kid go off on their own and feel nothing. The problem is you remember this kid when he was utterly helpless. And now, like, he's not. And part of your job is accepting that. Anyway we got him one of those pay-as-you-go phones and he called when he got to school, so it's fine. My ultimate aim is to raise a son who's independent and knows how to navigate a city. Besides New York in 2010, has nothing on Baltimore in 1985.
A quick aside, as always with these things, this is memoir and not public policy. I make no recommendations as to the proper technique for other people's kids. There is only one fifth-grader in this house. He's the only one I truly know.