I was looking at our family videos from this past winter and I found one of my son sledding down a hill backwards. As he’s approaching the bottom of the hill, he gives me a thumbs-up, hits an abandoned sled, careens into a ditch, and then wipes out.

I wondered if that ride backwards left an impression on him and, if so, what he made of it. His options are many. He could learn nothing. He could conclude that he is great at assessing his potential for success and unforeseen ditches cannot take away from the glory of that backward slide. He could conclude that he is not good at estimating risk and all his future endeavors could end up in a wipe out regardless of his forethought and preparation.

What do I hope that he will learn from it? I hope that he will learn that sometimes things that work well in theory, like backwards sledding, don’t work out in real life. I hope he will learn that some activities need our attention to the very end of the process and we can’t let our guard down or take our eye off the target before we reach our goal. I hope that he will learn that the fact that he overestimated his chance for success this one time does not mean that he should mistrust his judgment every time. I hope he will learn that just because his victorious thumbs-up was followed by a crash, not all his successes will be undone or undermined by soon-to-follow wreckage. I hope that he will use this experience to learn more about himself. I hope he will use this experience to recalibrate his risk assessment process. Most importantly, I hope that he will remember that wiping out once does not mean wiping out always.