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A few Halloweens ago my wife and I decided to let our son go out trick or treating on his own for the first time. To be sure, he wasn’t going alone—he’d arranged to go with a few of his friends—but at the end of October on the Canadian prairies it gets dark by six o’clock. With a certain amount of trepidation, I watched him step out the door in his gladiator costume and disappear into the night with his friends. This was new territory for us as parents.

It’s hard to know sometimes where the line is between being too overprotective and not protective enough. Some of his friends were allowed to roam the town at night on their own before they were even in their teens. Others seemed to be under constant lock and key. Neither approach is ideal in my opinion.

The most liberal-minded parents tend to say that kids these days are mature for their age and know a lot more about life earlier on, but knowledge doesn’t equal wisdom. Wisdom comes with time and experience—it isn’t innate. No one is born wise. You grow wise, if you’re lucky (some never do). I firmly believe that children must be guided toward wisdom and you can make that path as broad or narrow as you like. At the opposite end of the child-rearing spectrum are the helicopter parents who constantly hover around their children, softening every sharp corner in an attempt to keep them safe from all possible harm. The sentiment is noble, but the results down the road are often less than ideal. How’s a person supposed to function in the world when they leave home if they were never allowed to navigate any of it on their own beforehand?

As parents, my wife and I have always tried to find a balance between these two extremes. We make him aware of the pitfalls out there, but we don’t shield him from them entirely. As he’s grown older we’ve made incremental adjustments to the extent of his personal freedoms, slowly playing out the invisible rope that binds him to us. We’ve never thrown caution to the wind though. No preteen son of mine was going to rove about town after dark. I know kids, since I was one of them once (many moons ago). I know what some of them get up to when their parents aren’t watching. I also noticed that some of the kids who were allowed to run free from an early age weren’t necessarily better adjusted.

But by this particular Halloween our son was a teenager, although just barely so. I couldn’t think of a good reason to hold him back, except for my own fears and worries. So I watched as his friends and he were swallowed up by the darkness while they strolled down the street in their costumes. I felt uneasy, and a big part of me wanted to put a stop to it. My imagination tends to go to dark places when I don’t reign it in, and a highlight reel of horrible scenarios began playing out in my mind as I stood there. I imagined some creep in a van grabbing him and taking him out to the woods to do unspeakable things to him. I thought about him eating candies injected with poison and collapsing in the street as his friends stood over him with confused looks on their faces. I thought about what it would feel like if he didn’t show up at home by the time we’d agreed on. Would he answer his phone if I called or would a prerecorded voice say he was out of the service area? How long would I wait before leaping into our car and going out to look for him? Fifteen minutes? Thirty? An hour?

I needn’t have worried. Though he was to be home by eight-thirty at the latest, he walked through the door with his candy sack bulging just after eight. Relief washed over me like a cool wave on a sweltering day and all of those bad thoughts I was thinking were flushed away. Our son knew his boundaries, and though I was sure he’d test them in the years to come, I slowly began to reconcile the fact that this was all part of growing up.

That night as we laid in bed, my wife asked me if we should start allowing him to go out at night with his friends more often now. After some back and forth we both agreed that it would depend on where he was going and who he was going with. It would also depend on him. If he continued to respect and obey our rules, we’d give him more slack. If he didn’t, we’d have to take a step back and figure it out. Nothing is ever totally cut and dried when it comes to kids and parenting.

Now that he’s older still, we don’t worry so much about perverts and predators anymore. He’s big enough now that our fears of those things have lessened, though I realize that I’ll probably never feel entirely comfortable with the idea of him being out there by himself—not even when he’s an adult, which isn’t too far off. Another part of me knows that soon some of his friends will be starting to experiment with drinking, drugs, and other things. He’s even told me that a couple of his classmates already have. So now we have new things to worry about and new admonishments and warnings to impart. I hope he takes them to heart. I’m optimistic that he’ll have the sense to never get into a vehicle with someone who’s been drinking or decide to pop those pills the older guy at the party is handing out. We’ve warned him about such things, but much will depend on him now.

When I think about my own rocky road to adulthood and all the dumb shit I did, I cringe and hope that he has more sense than I did. I also finally understand what my own parents struggled with as they raised me and my brothers all those years ago. The old adage is true: once a parent, always a parent.  You never stop worrying about them. If we’ve done our job right, someday he’ll be in the same boat as us and the cycle will begin again.