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Honestly with Bari Weiss

Wisdom from a Teen and a Grandfather—60 Years Apart

29 min • 25 december 2023

Over the last six months, we’ve run two essay contests in The Free Press.


The first was for high schoolers; we asked them to write about a problem facing American society—and how to fix it. 


The second contest was for an older generation—70 years and over—and we asked them to tell a story about an event that shaped their life and helped give them wisdom or a fresh perspective. 


Today, we are thrilled to bring you the winners of both of those contests. Voices of wisdom exactly 60 years apart.


First, you’ll hear 17-year-old Ruby LaRocca read her winning essay, “A Constitution for Teenage Happiness.” As you’ll hear, her happiness guide involves less phones (in fact, she doesn’t own one) and more old books, less TV and more memorizing poems. Ruby is a homeschooled senior. She told us she entered the contest because she believes in our mission of finding “the people—under the radar or in the public eye—who are telling the truth.” 


Then, you’ll hear Michael Tobin—a 77-year-old psychologist living in Israel—read his winning essay, “A Love Song for Deborah.” It is about grappling with his wife’s Alzheimer’s diagnosis and nearly giving in to despair—until he found the one thing that awakened her. 


We hope you enjoy today’s episode, and that it moves, uplifts, inspires—and all of those other holiday spirit verbs. It sure did for us.

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