I HAVE A MASOCHISTIC need to please bosses, so I’m never more than a few feet from my iPhone (notifications humming at all hours) and I never leave home without a MacBook in tow. Just in case. My manager, who once mentioned pointedly that he has a “perverse respect for workaholics,” recently emailed me a question at 11:11 p.m. When I responded seven minutes later, he shot back: “You = Always On.”

Whether it was a joke or a compliment, I’ll take it. Different generations might debate which technological advance launched the...