Before applying for colleges, my daughter Maddie set a few broad criteria: She wanted a liberal arts college with a low teacher-to-student ratio, and she didn’t want to be in a big city. My main criterion was amorphous: I wanted her to be happy. But what is happiness? Does prestige matter? Would she be happier …

What a difference a year makes. This time last year, I was preparing to send my firstborn to the opposite coast of the U.S.—away from home longer than she’d ever been, without a family member within hundreds of miles. In the days leading up to her departure I kept asking myself…would she be warm enough? …

I knew it would happen someday. Surely every parent must deal with a situation in which a child says something so dreadful that there is no appropriate response. My daughter Winnie, at nineteen months old, uttered the words that I had particularly dreaded:

“I look PRETTY!!”

I froze, my mind already in denial, already telling itself that I had misunderstood her squeal. But, no, the words were clear enough. And, if there was any question, there she was, twirling around the living room, admiring the ruffles on her new dress. The dress itself was a gift from a relative, and it was an adorably girly concoction of flounces and sparkles. The kind of thing that I, her mother, would never have bought for her.

No sooner was the dress over her head than Win began a series of spins that would have made any prima ballerina proud. “I LOOK PRETTY!!” she howled again.

I’m a problem-solver. A can-do kind of person. I take the bull by the horns and make things happen. None of which helps me when it comes to my daughter and her friendship challenges. Once we have babies we transform into People Who Get Stuff Done, regardless of who we were before. There is no such …