Unexpected Encouraging Words: “You Might Fail”

My dad, Sonny, always had plenty of advice to offer but he wasn’t the type to pipe up with unsolicited input. If you wanted to know what he thought about something, you needed to ask. His face gave away little unless he wanted you to see what he was thinking. It was a vocational asset when he needed to maintain a fixed, non-committal visage during high stakes meetings and mediation marathons in his work life.

When I was little, I’d eavesdrop when he was embroiled in heated, time-sensitiv...