John Riddle
on November 13, 2026

A Little Advice, a Lot of Love: Life Lessons From Pop-Pop

Take the time Sunday to write a letter to your grandchildren!

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6 min read

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A grandfather’s letters offer something children can carry long after they have outgrown his lap.

A grandchild can outgrow the toys you bought, the clothes you picked out and even the bicycle you helped assemble. The words you leave behind have a chance to grow more valuable.

Advice that earns a shrug at 12 may offer reassurance at 22. A story about a mistake you made can mean something different when a grandchild faces a difficult decision. And a letter can wait patiently for the day its reader needs it.

For Delaware author John Riddle, known as Pop-Pop to his six grandchildren, that possibility became the heart of Letters From Pop-Pop: Advice For Grandkids Everywhere.

“In a world full of distractions and fast answers, I wanted to create something that feels real and lasting,” Riddle said.

The result is a collection of 25 letters about the everyday choices that help shape a life: showing respect, practicing patience, choosing kindness, handling money, managing time and persevering when things go wrong.

These are subjects grandparents know something about. They have had time to discover which worries fade, which choices matter and how often getting back up counts for more than getting something right the first time.

The challenge is finding a way to share those lessons that invites a grandchild to keep listening.

Riddle chose letters.

“Letters From Pop-Pop is my way of passing down the values I hope my six grandkids, and every child, will carry with them,” he said.

Each letter includes a motivational quote and a practical challenge, giving readers something to consider and something to try. A conversation about kindness, for example, can continue beyond the page as a child looks for ways to practice it.

Author, coach and Pirate Preacher Eddie Jones appreciated that approach.

“I like how each letter gives solid advice and then a little challenge for readers to apply. Feels real,” Jones said.

He also pointed to the quality that can make the difference between advice children tolerate and words they welcome.

“Also, I like that Pop-Pop doesn’t lecture. He talks to you. That’s what makes it work.”

That distinction matters. Grandchildren have plenty of people telling them what to do. A grandfather has an opportunity to explain what he has learned, acknowledge that life can be difficult and offer encouragement without requiring an immediate answer.

A letter gives both generations room. The writer can take time to say what matters. The reader can return to it privately, ask a question later or discover a new meaning years afterward.

For Michael F. Schein, founder of MicroFame Media and author of The Hype Handbook, Riddle’s book brought his own grandfather to mind.

“I regularly think about quotes from my Pop Pop (yes, I called mine that too!) and I wish I had had this book back when I used to sit and listen to his stories and wise tidbits,” Schein said.

His response touches on something many adults recognize only after childhood has passed: the wish to hear a familiar story once more, ask another question or remember exactly how a grandparent used to say something.

Riddle’s book includes space for personal notes and photographs, allowing families to add their own voices and memories. A grandfather can write beside a lesson, explain why it matters to him or include a picture that opens the door to a family story.

Those additions can turn a shared book into a distinctly personal keepsake.

The name on the front need not be the name a family uses at home.

“Although my 18 grandchildren call me Baba, not Pop-Pop, John Riddle’s book is a helpful and down-to-earth guide for children to develop a healthy and helpful attitude which will bless them throughout their lives,” said Dr. Ted Baehr, founder and chairman of Movieguide.

For grandfathers considering letters of their own, Riddle’s collection offers a place to begin. Read a letter together. Talk about its subject. Share a memory it brings to mind. Then leave a few words in your own handwriting.

You do not have to fit a lifetime of wisdom onto one page. One honest story, one useful lesson or one expression of pride is enough to start.

Someday, a grandchild may open that page looking for advice. What they will also find is evidence that someone thought about the life ahead of them and cared enough to put it into words.

Letters From Pop-Pop: Advice For Grandkids Everywhere by John Riddle is available on Amazon.

John Riddle Bio:

He is a Delaware author of 44 books and has worked as a ghostwriter on numerous projects. His byline has appeared in major publications across the U.S., and he has written articles for over 200 websites. In 2002 he launched “I Love To Write Day” as a grassroots campaign to have people of all ages spend time writing every November 15th. Learn more at ilovetowriteday.com 

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