How to Handle Rejection When You Never Applied

‘There’s something worse than going 0 for 1.’

Many high-school students are waiting in agony for replies to their college applications. But surely there’s something worse than waiting: rejection. At least that was my thinking—that straight-up rejection is the low point—before I spoke recently with my younger brother, Jack. It was on my mind when I called him, since my eldest son is waiting to hear back from a handful of colleges.

Jack pointed out a flaw in my logic by reminding me of a rejection letter he received while a law student at the University of Virginia. The...