One Generation to Another

AI is everywhere. It answers our customer service calls, drowns social media in weird (sometimes funny) videos, and can customize our schedules for the next month. And family history? It’s not immune to the AI takeover.

There are programs that promise to turn a family’s history into a polished book. Some families feed recordings of Grandma and Grandpa straight into a chatbot, hoping to score a sentimental Christmas present. AI can be a great tool for gathering and recording your family’s details. But that doesn’t make it a good storyteller.

Beyond getting facts wrong and missing the emotional weight of a story, AI simply can’t do what a human can: listen closely enough to find the story worth telling. In this episode, Melissa and Dave explain what’s at stake—and what can be lost—when families hand their stories over to machines.

Resources:

We reference the following two episodes in our latest release. Be sure to give them listen below!

How Can We Uncover the Meaning Behind Our Family’s Stories?: https://www.journeysixty6.com/blog/one-generation-to-another-how-can-we-uncover-the-meaning-behind-our-family-s-stories

How Do We Uncover the Stories Our Family Never Told?: https://www.journeysixty6.com/blog/one-generation-to-another-how-do-we-uncover-the-stories-our-family-has-never-told

Do you want to capture your family story but don't know where to start? Check out our process: https://www.journeysixty6.com/

Take a spin through some of our published Legacy Keepsakes: https://www.journeysixty6.com/published-family-business-books

If you’d like a conversation with Dave and Melissa to learn more, please visit: https://www.journeysixty6.com/schedule-a-15-minute-consult-

Human stories are what bring a family history to life. But when a family leader first starts on the journey to capture and tell their family’s history, they drift towards collecting facts: how the family business started; who led it; what the major milestones were.

Those details matter, but on their own they lack the meaning that transforms a historical retelling into a legacy story. That meaning, the kind that carries real lessons for future generations, is often buried beneath the facts. 

So, how do you uncover those deeper stories a family has never told?

Melissa and Dave answer that question in this episode of One Generation to Another.

Do you want to capture your family story but don't know where to start? Check out our process: https://www.journeysixty6.com/

Take a spin through some of our published Legacy Keepsakes: https://www.journeysixty6.com/published-family-business-books

If you’d like a conversation with Dave and Melissa to learn more, please visit: https://www.journeysixty6.com/schedule-a-15-minute-consult-

Most families collect their history the same way. Someone sits down with Grandma, hits record on their phone, asks a few questions, and hopes something lasting comes out of it. Usually, families walk away with a handful of stories they’ll never forget.

But a collection of great stories isn’t the same thing as a legacy. Without context, those stories are mere events—things that happened. They may be vivid, but they’re disconnected, and don’t convey meaning.

That is what Melissa and Dave dig into in this episode. History, as they explain, tells us what happened, but it’s legacy that helps us understand how experiences shaped beliefs, values, and purpose. To get you from history to legacy, Melissa and Dave share five questions that will help you turn a routine family interview into something that pulls meaning out of memory.

Do you want to capture your family story but don't know where to start? Check out our process: https://www.journeysixty6.com/

Take a spin through some of our published Legacy Keepsakes: https://www.journeysixty6.com/published-family-business-books

If you’d like a conversation with Dave and Melissa to learn more, please visit: https://www.journeysixty6.com/schedule-a-15-minute-consult-

When families begin capturing their history, they often are overwhelmed with decades of stories and dates of events, hundreds of photographs and documents to sift through, and dozens of people to interview. Knowing where to begin can feel daunting.

One of the simplest ways to organize your family story is to identify the moments when something shifted—within the family, the business, or both. We call those defining moments tentpole scenes. Often families have five to seven of those pivotal turning points.

In this episode of One Generation to Another, Melissa and Dave explain what tentpole scenes are, how to identify the defining moments in your family’s history, and how supporting stories further bring those turning points to life—so you can create a history that is readable, memorable, and meaningful for the next generation.

Do you want to capture your family story but don't know where to start? Check out our process: https://www.journeysixty6.com/

Take a spin through some of our published Legacy Keepsakes: https://www.journeysixty6.com/published-family-business-books

If you’d like a conversation with Dave and Melissa to learn more, please visit: https://www.journeysixty6.com/schedule-a-15-minute-consult-

When family businesses first set out to capture and preserve their story, they expect to end up with a physical product—a memoir, a documentary, a coffee table book. That final product is part of the process, but what we at Journey Sixty6 actually create is something lasting: a Family Legacy Keepsake.

In this episode of One Generation to Another, Melissa and Dave get to the heart of what a Family Legacy Keepsake really is. They explain how it’s fundamentally different from a regular, historical record. A Legacy Keepsake can take on many different forms, depending on the story the family wants to tell.

Do you want to capture your family story but don't know where to start? Check out our process: https://www.journeysixty6.com/

Take a spin through some of our published Legacy Keepsakes: https://www.journeysixty6.com/published-family-business-books

If you’d like a conversation with Dave and Melissa to learn more, please visit: https://www.journeysixty6.com/schedule-a-15-minute-consult-

Many family history projects begin with curiosity. The family project’s leader sifts through photographs, journal entries, newspaper articles, piecing together whatever they can find. That research is the bedrock of the entire project. But most family project leaders don’t know what type of research they actually need, or how much of it is enough.

In this episode of One Generation to Another, Melissa and Dave break down the three main types of research that go into a family history project. And they share the signs that tell you when you’ve gathered enough to start telling your story.

Do you want to capture your family story but don't know where to start? Check out our process: https://www.journeysixty6.com/

Take a spin through our published books: https://www.journeysixty6.com/published-family-business-books

If you’d like a conversation with Dave and Melissa to learn more, please visit: https://www.journeysixty6.com/schedule-a-15-minute-consult-

No family story is without its hard moments. There is conflict between generations, disagreements among siblings, and frustrations over business decisions. Most families who begin capturing their family story recognize this. They get stuck, though, figuring out what role conflict should play in the story handed down to future generations.

In this episode of One Generation to Another, Dave and Melissa explore how families can acknowledge conflict honestly without allowing it to define the family’s legacy. They cover:

The goal of a Family Legacy Keepsake is to create a story that is honest and useful to future generations. It shouldn’t erase conflict, but it shouldn’t memorialize it either.

Do you want to capture your family story but don't know where to start? Check out our process: https://www.journeysixty6.com/

Take a spin through our published books: https://www.journeysixty6.com/published-family-business-books

If you’d like a conversation with Dave and Melissa to learn more, please visit: https://www.journeysixty6.com/schedule-a-15-minute-consult-

Most Legacy Keepsake projects are a lengthy process. You would think that, after multiple reviews and revisions, the family would be eager to publish their Keepsake. Yet we’ve noticed the opposite to be true. As the end draws near, families tend to slow down. They nitpick over sentences, second-guess the stories, and wonder if they’re getting the overall story right. Letting go of the project often makes families feel vulnerable.

On this episode of One Generation to Another, Melissa and Dave explore why families struggle to let go of their Keepsake. They discuss:

Do you want to capture your family story but don't know where to start? Check out our process: https://www.journeysixty6.com/

Take a spin through our published books: https://www.journeysixty6.com/published-family-business-books

If you’d like a conversation with Dave and Melissa to learn more, please visit: https://www.journeysixty6.com/schedule-a-15-minute-consult-

Most families assume their Legacy Keepsake is simply for the family.

It’s a way to help future generations understand the sacrifices, values, and moments that shaped the family business and family wealth. Through story, those values become tangible—and motivating.

But once the process of capturing a family legacy begins, something unexpected often happens: the Keepsake starts reaching a much wider audience than originally imagined.

In this episode of One Generation to Another, Melissa and Dave explore the different audiences a Legacy Keepsake can serve, including:

A Legacy Keepsake may begin as a gift to future generations, but its impact can extend far beyond the family itself.

Do you want to capture your family story but don't know where to start? Check out our process: https://www.journeysixty6.com/

Take a spin through our published books: https://www.journeysixty6.com/published-family-business-books

If you’d like a conversation with Dave and Melissa to learn more, please visit: https://www.journeysixty6.com/schedule-a-15-minute-consult-

Most families come to us with something they want to preserve for the next generation. Sometimes it’s a book or a digital archive. More often it’s just a feeling that something matters and shouldn’t be lost. What they don’t expect is how much the process itself gives back. 

In this episode of One Generation to Another, Melissa and Dave explore the deeper outcomes families experience when they begin capturing their family legacy.

In this episode, we explain: 

Do you want to capture your family story but don't know where to start? Check out our process: https://www.journeysixty6.com/

Take a spin through our published books: https://www.journeysixty6.com/published-family-business-books

If you’d like a conversation with Dave and Melissa to learn more, please visit: https://www.journeysixty6.com/schedule-a-15-minute-consult-