I make it a point to ask my Uber drivers how their day is going, maybe even strike up a conversation about where they’re from or what they do. Those who are receptive to it turn it into a peaceful conversation — something to pass the time on the drive. Sometimes it doesn’t go anywhere, and you just have to respect that, but most of the time you can tell they appreciate your empathy and will engage just as far as you’re willing.

The first person to say it to me was my Uber driver. The next was my mom, then my best friends. The last time I said it was nervously at 11:58 p.m. after an emotionally taxing day to the guy that had been...