Amazingly, it was a bet that I would have lost.

My then-wife insisted on keeping watch over the house the night Sandy hit, just in case the branch—which we'd reported to the city and been told would be addressed at some point, but don't hold your breath—should inevitably fall and crash into the roof. The updates via text throughout the night were increasingly unnerving, and eventually were silenced. By morning, no one in Staten Island had cell service any longer and almost no one I knew had power. When I reached my house, I was shocked to discover that the tree in front of the house remained mostly intact.

The ones in the backyard, however, were a different story.

Four of them, all Bradford Pears—tall, seemingly firm trees about which I had little worry, were uprooted or destroyed, split into pieces as huge branches tore away from the trunks. The entire yard looked like a war zone, large branches strewn everywhere. One tree had split in two; another lay snapped at the base of its trunk.

Like many Staten Island residents, we had an above-ground pool; one of the trees had fallen on it, effectively rending one of the sides beyond repair.

Therein lies the irony. I spent so much time worrying about the catastrophe that I thought would occur, and didn't, that I ignored the potential peril at the other end. In the process, I learned a valuable lesson about embracing the bigger picture when it comes to calculating risk—and the myriad things that could go wrong that must be considered. For one thing, we ended up suffering some roof damage that was more serious than I thought we would. I hadn't been counting on that, either.

Since this was my first major property damage claim, it was also my first experience with how my carrier would respond. Within three weeks—a very short time, considering how badly many others in my borough fared, with far more serious claims—my insurer had dispatched a claims investigator who found things we would never have looked for: water damage in the walls of our bedroom, for instance. We hadn't even noticed it—but he did. The aforementioned roof damage, the extent of which we might not have realized until long after the claim was settled, was another.

This first claims experience, in short, was a positive one—and a reminder to those who work in the insurance business that those entrusted in helping to rebuild peoples' lives and return them to something resembling normalcy would do well to remember that the service they provide reflects widely on the industry at large. And in my case, affirming the covenant of trust that exists between the insurer and insured.