Two incidents will illustrate.
Early 2013: I take my quite-young kids to hike to the summit of Mt Taranaki. The ascent is more grueling than I expected; there's a long scree slope which is two steps forward, one step back. My kids start complaining, then crying. I have to decide whether to turn back or to cajole them onward. There are no safety issues (the weather is perfect and it's still early in the day), but the stakes feel high: if I keep pushing them forward but we eventually fail, I will have made them miserable for no good reason, and no-one likes a parent who bullies their kids. I roll the dice and press on. We make it! After the hike, we all feel it was a great achievement and the kids agree we did the right thing to carry on.
Two weeks ago: I take my kids and a couple of adult international students from our church on an overnight hiking trip to the Coromandel Peninsula. On Friday we hike for four hours to Crosbies Hut and stay there overnight. It's wonderful — we arrive at the hut around sunset in glorious weather, eat a good meal, and the night sky is awesome. The next day I return to our starting point, pick up the car and drive around to Whangaiterenga campsite in Kauaeranga Valley so my kids and our guests can descend into the valley by a different route that crosses Whangaiterenga stream a few times. I had called the visitor's centre on Friday to confirm that that track is open and the stream crossings are easy. My kids are now quite experienced (though our guests aren't) and should be able to easily handle this on their own. I get to the pickup point ahead of schedule, but two hours after I expected them to arrive, they still haven't :-(.
To cut the story short, at that point I get a text message from them and after some communication they eventually walk out five hours late. They were unable to pick up the trail after the first stream crossing (maybe it was washed out), and had to walk downstream for hours, also taking a detour up a hill to get phone reception temporarily. The kids made good decisions and gained a lot of confidence from handling an unexpected situation on their own.
What bothers me is that both of these situations could easily have turned out differently. In neither case would there have been any real harm — the weather in Coromandel was excellent and an unexpected night in the bush would have been perfectly safe given the gear they were carrying (if indeed they weren't found before dark). Nevertheless I can see that my decisions could have looked bad in hindsight. If we make a habit of taking these kinds of small risks — and I think we should! — then not all of them are going to pay off. I think, therefore, we should be forgiving of parents who take reasonable risks even if they go awry.