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In rainy Vancouver, where I grew up, the rare snowfall became an event. Swaddled in borrowed ski clothes, we hiked to the local hill high above the beach, and lay stomach-down on our toboggans, feeling what it is to fly.

That memory resurfaced this week as I peered down the well-worn hill at our local park in Toronto, littered with discarded garbage bag-sleds, the trail a muddy brown. And then a little kid – the size of a large teddy bear, really – zipped down on her red toboggan, squealing happily. I had a kill-joy thought: Would it be weird if I ran after her with a helmet?

As a cyclist with scars, I'm a helmet evangelist, but I'm not so proud of this – it puts me in league with the dreaded "bubble-wrap" parents who strap knee-pads on crawling babies and think they can prevent all harm. To me, the helmet symbolizes a loss: This generation of sledding kids will never know that losing the toque is a sign of a great run, or feel the wind in their hair as they speed away on a bicycle.

So much of parenting is a refraction of our own childhoods. The decisions we make are often a nostalgic act, for better or worse. A recent book called Parent-Babble: How Parents Can Recover From Fifty Years of Bad Expert Parenting, by syndicated American columnist John Rosemond, asserts that we should all return to parenting the way our folks did back in the old days when young people never committed suicide, self-mutilated or talked back, and winged pigs circled overhead.

Rosemond blames decades of psychologists exalting self-esteem over "proper social decorum" and suggests parents take their lead from "elders" and community leaders. Well, okay – who isn't in favour of stronger communities and inter-generational wisdom?

But Rosemond comes down absurdly hard on today's parents, furnishing a particularly conservative strain of sky-is-falling panic with his romantic idealization of his 1950s childhood (my parents were kids in the forties and pepper their tales of jazz bands and proms with memories of peers mired in sadness and neglect). Rosemond's ye olde childhood is fantasy; like all nostalgia, it's an ache for something that never was. Similarly, I'm projecting my own childhood onto my kids when I mourn the helmet-free bike ride or lament the fact that their favourite toy is my smartphone.

Today's kids live in a very different world, one in constant motion, a blur of computers, cell phones, blended families, ADHD diagnoses – a world with Psy in it. Some of grandpa's wisdom is relevant now; some useless. As Lisa Belkin wrote on The Huffington Post in an excellent critique of Rosemond's book: "We cannot wish the social changes away. We shouldn't want to, because so many of them – gender equality comes to mind – are hard-won victories. But while we have probably overshot in our response to this new, unsettling world, and while it is certainly time to rethink and ratchet back our parenting, nostalgia for the good old days will just set us turning in circles."

I wondered if I was turning in circles when our kids started to walk to school this year. This old-school act involved much 2012-style preparation: mapping the route, talking and stranger-proofing, and a few trial runs with some parental skulking behind trees and fences, Scooby-Doo style.

In 2008, when Lenore Skenazy wrote a column for The New York Sun about letting her then nine-year-old son ride the subway in New York, several media outlets dubbed her "the worst mom in America." But as she points out in her book Free-Range Kids, kids are actually safer than they've ever been. In the United States, the FBI estimates that a child is 25 times more likely to be killed in a car accident than by a predator. Crime is down in both the U.S. and Canada.

But where kids are concerned, the extreme and the tragic are the stories that make the news and feed the fear.

Recently, the premier of Ontario, Dalton McGuinty, lunged for some easy points after the terrible Newtown killings, promising to lock schools province-wide, at a cost of $10-million (this during a tumultuous labour dispute with teachers' unions). Schools are one of the last public gathering places that aren't trying to sell us stuff. They should be more open to their neighbourhoods, not less. Maybe buzzers aren't a big deal, but the idea of constant fortification and viewing the community closest to our kids as threatening is.

Perhaps the best way to assuage the fear is to parent with balance, acknowledging the realities of contemporary life and invoking the more intelligent habits of the past. Walking to school is healthier; they arrive home with a swagger of accomplishment and independence. Turns out that particular parenting decision wasn't about my nostalgia but their freedom – no helmets required.

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