Advisors
I've linked the Art of Manliness article on "the five-second moment" in the "What makes a family story worth retelling?" section, where the term is first defined. Here's the full post again with that link added. Copy everything below the line into Framer. The podcast embed code still goes in a separate Embed component.
The short answer: Advisors can help families keep their legacy alive by encouraging them to capture small moments as they happen, find the meaning in them, and tell them often. Storyteller Matthew Dicks suggests a simple starting point: one sentence a day about the moment you don't want to lose. It costs clients nothing, and it gives you a human way into legacy conversations.
Most legacy work starts late. Alex Kirby, founder of Total Family, put the usual approach bluntly on the Visionary Advisor podcast: "wait until you're 85 and then try to write down everything that you could possibly think of."
Your clients don't have to work that way. In this episode, Alex talks with Matthew Dicks, an author, storytelling consultant and retired elementary school teacher, about how families can hold on to their lives as they live them.
Key takeaways
Stories carry what documents can't. Context, values and meaning travel through stories. Research from Emory University associates family storytelling with children's well-being, and many families have already lost basic details such as grandparents' names.
Small beats big. A one-sentence daily note keeps moments from disappearing. Most won't become full stories, but all of them become part of a family's record.
Meaning matters more than detail. A photo or text message fades without the thought or feeling behind it. Encourage clients to record what they felt and why it mattered.
Honest stories connect families. Sharing difficult chapters, with consent, builds closeness. You can help clients move beyond the "we rose from nothing" story toward one that includes setbacks and recovery.
You can start with one question. Story-first questions give clients a way into legacy conversations that documents alone often can't.
Why should advisors care about client family stories?
Because stories carry what documents can't: the context, values and meaning behind a family's wealth. Alex believes advisors are "the keepers of legacy" because they've already earned the trust needed to talk about values and family history. Stories give that trust somewhere to go.
Alex opened the episode with a story that shows why this matters. Marjorie Findlay was a Memphis-born singer who toured as an opera performer, then chose a quieter family life. As Alex told it, she wasn't wealthy "by wealth management standards," but she passed a love of music to her granddaughter, who became the musician Taylor Swift and later wrote a song called "Marjorie." Alex's takeaway: "We'll never know which part of ourselves will carry the next generations forward." Your clients' legacy isn't only what's on the balance sheet.
The research supports treating this as real planning work. Psychologists Robyn Fivush, a previous guest on the Visionary Advisor podcast, and Marshall Duke developed the "Do You Know?" scale, 20 yes or no questions such as whether a child knows how their parents met or where their grandparents grew up. In their studies, adolescents who knew more family stories showed higher emotional well-being and a stronger sense of identity. These are correlations, not proof of cause, but they're a strong reason to bring stories into the conversation.
Many families don't hold on to them. A 2022 Ancestry survey of 2,113 Americans, conducted by OnePoll, found that 53% couldn't name all four of their grandparents.
Matt adds a human reason. While researching a book, he interviewed hospice workers, who told him that one of the greatest regrets people share at the end of life is not feeling they lived a full enough life. His response: they probably did, but they can't remember much of it. Capturing moments along the way lets people look back on "a long road filled with memories and experiences and triumphs and tragedies," as he put it.
What this means for you: Clients who can tell their family's story are more likely to articulate what they want their wealth to do. That makes your planning conversations richer, and it builds the kind of trust that extends across generations.
How can you help clients find stories worth keeping?
Introduce them to Homework for Life, a daily habit created by Matt. Each day, the client asks which moment they'd tell a story about if they had to and writes one to five sentences in a spreadsheet or notes app. They're not writing the story. They're marking the moment so they can find it later.
Matt began the practice in 2012. His early entries averaged about 1.1 moments per day because he was looking for finished stories. Today he captures almost eight a day, because he now looks for moments of meaning he doesn't want to lose, knowing most won't become stories but will become part of his legacy. His life isn't more interesting now, he says. He's just paying closer attention.
Three ideas from Matt make this easy to recommend.
Don't judge what's worth recording. It costs nothing to add a line to a spreadsheet. Matt points out that people are often in the middle of a story without realizing it, and they'll never recognize it if they don't record the moments leading up to it.
Capture thoughts and feelings, not just facts. Matt recently copied a friend's text message into his log. The text already existed on his phone, so why copy it? Because he's curating his life, and what mattered was how it made him feel, not the message itself.
Keep it small. Alex has done the practice since he read Matt's book. One entry came from his five-year-old son, who finished moving trees in the backyard and reported, "good news, bad news." The bad news was that he and his brother both needed the bathroom. Alex says he never would have remembered it without writing it down.
Share with your clients: Try Homework for Life for two weeks. One shared spreadsheet or notes app, one line a day, and everyone in the household can add to it, including the kids.
What makes a family story worth retelling?
A story is worth retelling when it centers on a moment of change. Matt calls this the five-second moment: an instant when you realize something or when you become different from who you were. It might take years to get there, but the change itself happens quickly.
Matt says most people report on events instead of telling stories. A vacation summary, a dream, a dinner menu: none of these is a story unless something shifted. "Stories are about moments of transformation or realization," he explained.
This is where family progress gets lost. Matt says: "There's no evolution if you don't know where you once were." He gave an example from his teaching career. He could see a student's growth in math over time, but parents often can't, because every day feels like the same struggle. Looking back, a child who once couldn't add and is now struggling with long division has clearly made progress. Alex sees the same pattern with families who improve a relationship, such as between siblings, then forget there was ever a problem.
What this means for you: Families often make more progress than they realize. When a client says a family conversation never goes anywhere, ask them to look back. Recorded moments give them evidence of change, which helps them keep going.
Share with your clients: When something shifts, jot down where you started. A short note like "first time we all talked about the will without an argument" becomes a marker you can return to years later.
How can clients tell stories so the next generation remembers them?
Open with a place and an action, give the story something at stake, and avoid announcing what's coming. Matt says this works because the brain recognizes it's hearing a story and pays attention. Instead of "my name is Alex, I'm 32 and I have two kids," try "I'm sizzling salmon in a pan when I hear a bang in the basement."
Matt believes that once the brain recognizes a story, it releases chemicals that help attention and memory. Research gives partial support. Paul Zak's studies found that stories with a dramatic arc raised cortisol and oxytocin in viewers, which he links to attention and empathy. Separately, Princeton neuroscientists found that a listener's brain activity aligns with the storyteller's, and that stronger alignment goes with better understanding.
Here are the techniques from the conversation that clients can use.
Use names. Saying "my friend Chris" is more vivid than "my friend," because listeners picture a real person. Matt says the goal is vividness, not accuracy. Don't over-describe, either. Say "kitchen" and let listeners use their own kitchen unless the details matter to the story.
Build in stakes. Stakes are what the storyteller wants, needs or fears. "I cooked dinner and it turned out great" has none. "My girlfriend is coming over and it's the first time I've cooked for her" does.
Skip the preamble. Don't say "this is the funniest thing you'll hear today," because humor depends on surprise. Don't say "this is the story of how your mother and I had our first kiss," because you've already told the ending. Matt's least favorite opener is "guess what," and he says the right response is "no thank you" and to walk away.
Use second person when telling someone else's story. For stories about parents or grandparents, Matt suggests guiding the listener's view with "you." Matt also says it's fine to tell other people's stories, but they rarely land as well as your own because they lack vulnerability. A family history story gets stronger when the teller adds what they thought or felt.
And one reassurance clients may need: Matt says, "I'd rather hear a story told poorly than no story at all."
What this means for you: Clients often say they're not storytellers or that their kids aren't interested. Matt's view is that kids don't dislike family stories; they just haven't heard them told well, since they happily watch movies and television that are told well.
Share with your clients: Pick one family story about a grandparent. Tell it to a child, starting with a place and an action, using real names, and leaving out the "guess what."
How do you bring storytelling into client meetings?
Make it a small, repeatable part of the relationship instead of a one-off project. Alex notes that retreats costing thousands of dollars and days of time don't work for most families, who don't have the money or the time. Small habits fit around work and parenting.
Here are ways to bring this into your practice.
Ask story-first questions. "What's a moment from this year you wouldn't want your grandchildren to miss?" opens a different conversation than "Who are your beneficiaries?" Matt's own prompt also works: "If I had to tell one story about today, what would it be?"
Help clients attach meaning to what they keep. A short note explaining why an object, photo or decision mattered can be worth more than the item itself.
Introduce legacy letters or milestone records. Help clients give their stories a place to live. A legacy letter can pass a story's lessons to the next generation, while a milestone record can capture a meaningful turning point and a saved quote can preserve a loved one's own words. Total Family's platform keeps these pieces together with the context that makes them meaningful.
Live it yourself. Alex says authenticity matters: if you don't love this work and live it in some way, it falls short. Starting your own Homework for Life is the quickest way to find out how it feels.
Point families to Worth Keeping. At the end of the episode, Alex announces a new podcast for families hosted by Matt and Medley DeLeonibus. Matt says every strategy on the show will be inexpensive or free, quick and easy, and often something kids can do. It's a ready-made resource when a client asks what they can do themselves.
Frequently asked questions
How can advisors start a family storytelling conversation with clients?
Start with an open question about a moment or memory instead of a document or account. For example, ask which family story the client most wants their grandchildren to know, then ask why it matters to them. The reasons often reveal their values.
What is Homework for Life?
Homework for Life is a daily practice created by storyteller Matt Dicks. Each day, you record one moment worth remembering in a few sentences, usually in a spreadsheet. The goal is to capture moments, not write finished stories, so you have material to draw on later.
What is a five-second moment?
A five-second moment is Matt's term for the instant a story turns on: a realization or a change in who you are. A story might cover years, but it hinges on one moment of transformation or new understanding.
Do clients need to be good storytellers to preserve their legacy?
No. Matt says he'd "rather hear a story told poorly than no story at all." Capturing the moment matters most, and techniques like opening with a place and action and using real names can improve the telling over time.
Listen to the Full Episode
The full conversation with Matthew Dicks is available now on Apple Podcasts, Spotify, and YouTube.
If this episode gave you a new way to think about starting family wealth conversations, subscribe to Visionary Advisor and share it with another advisor who wants to help families do legacy better.
