Advisors
The short answer: Advisors can help clients start legacy work by making the first step small and imperfect: a draft to react to, a short letter, an afternoon with old photos. Economist cartoonist Kevin Kallaugher has met deadlines for almost 50 years with one rule: get something on the page. Add well-aimed humor and heavy family conversations get easier to start.
Most clients don’t put off legacy work because they don’t care. They put it off because it looks enormous and solemn: a blank page, a heavy subject and a nagging sense they need to get it right first time. Even Alex Kirby, founder of Total Family, admits on the Visionary Advisor podcast that “even though I love legacy, I struggle to look back at that stuff because I’m trying to go forward.”
In this episode, Alex talks with Kevin Kallaugher, the editorial cartoonist known to readers of The Economist as KAL. Kevin became the magazine’s first resident cartoonist in 1978, spent decades at The Baltimore Sun, and is a two-time Pulitzer Prize finalist. By his count he’s published more than 11,000 cartoons and 150 magazine covers.
Key takeaways
Start with a draft, not a blank page. Clients engage faster with something to edit, even something they dislike.
Small legacy letters count. Favorite movies and family origin stories are real first steps, and writing them changes the writer.
Look back together while you still can. The older generation holds the stories that make objects meaningful.
Use humor like a stiletto. Well-aimed, self-deprecating humor builds trust. Mean humor erodes it.
Connection needs a cadence. Regular, low-stakes contact keeps families and next-generation relationships from drifting.
How can advisors help clients get past the blank page?
Give clients something to react to. Kal’s rule from five decades of deadlines: “you just gotta get something on the page and it doesn’t have to be perfect.” A draft gives people something to edit, and editing produces ideas a blank page never will. For advisors, that means swapping open-ended legacy questions for small prompts and draft statements clients can accept, reject or reshape.
Try to work everything out in your head first, Kal warns, and “you’re gonna be thinking about a thing for about 100 times longer than you need to.” He also expects to miss. Behind every cartoon readers loved were “10 lousy sketches” he learned from.
Total Family’s purpose statement exercise works the same way. Clients answer six questions, are placed in a purpose category (builder, protector or connector, for example), then choose one of eight statements and edit it however they like. “Once you give someone a statement and they select it, it doesn’t matter if they love it or they hate it,” Alex said. “They now have something to work with.” Even “I hate it” moves things forward, because the next question is what they’d change.
What this means for you: Don’t wait for clients to arrive with a fully formed vision. Bring a draft, such as a starter values list, a sample purpose statement, or the first line of a letter, and ask what’s wrong with it. What a client rejects often tells you more about their values than a questionnaire would.
What should a client’s first legacy letter look like?
Short and ordinary. Alex points out that a legacy letter doesn’t have to be “the I’ll never see you again letter.” It can be the three movies a client loves, the books that changed their life or why the family ended up where they live. Lower stakes mean clients actually write something.
The writing also changes the writer. Kal’s mother, Barbara Kallaugher, wrote her memoir late in life over a couple of years. Some chapters weren’t happy ones, and Kal calls it “a healing process” for her. She went on to teach a memoir class at her retirement community, telling people the work would “enrich you” and “enrich your family.” As Alex put it: “I do also think this changes the writer.”
Research points the same way, with caveats. Harvard Health’s summary of James Pennebaker’s expressive writing research says writing about difficult experiences may help some people make sense of them, but it isn’t a cure-all. Offer it as an option, not a treatment.
What this means for you: A light first letter is easy to recommend and easy to finish, and it gives you a window into what clients value.
Share with your clients: Write a letter to your children or grandchildren that’s just a list: three movies you love, the book that changed your life and one line on why each one matters to you.
Why should families look back together while they still can?
Because the person who can explain the story may not be there later. Alex notes that most families go through old photo albums at a funeral when “the person that knows can’t answer.” Reviewing archives and keepsakes while the older generation is alive turns objects into stories and gives everyone a chance to ask questions.
Kal did exactly this. Before his collection went to The Ohio State University’s Billy Ireland Cartoon Library & Museum, which lists the donation as 114 boxes of original art, he and his family spent hours in an airless storage locker going through the cartoons. His children chose pieces for their own collections. Hearing them laugh was a rare reward for someone whose job, he says, is like being “a standup comedian with the audience in the next county.” And, he adds, “you learn a lot about yourself in this process.” Alex found the same at home: reading Kal’s retrospective, Daggers Drawn, with his six-year-old son bridged a 40-year age gap.
What this means for you: Photos and keepsakes are often the most emotionally loaded things a family owns and the least documented. A shared review preserves the context and shows who cares about what before anything becomes an estate question.
Share with your clients: Pick one box of photos or one collection and go through it with your children or grandchildren. Record the stories as you go, especially the names and dates only you know.
Should advisors use humor with high-net-worth families?
Yes, with care. Alex has noticed that advisors often avoid levity with wealthy families for fear of seeming to downplay serious matters. Kal argues that a well-placed bit of humor “can break the logjam” in tense or grieving rooms. Start with self-deprecating humor, which he calls “a safe place to go”: it signals confidence and makes you more approachable.
Kal sees his cartoons as visual columns: “My job is not to make people laugh, but to make them think, but using humor as a vehicle for a message.” Early in his career, an editor at The Economist told him “a stiletto is much more effective than a sledgehammer.” The aim is to engage people, including those who disagree with you, not to wound them. Alex agrees: the best roasts come from a place of love, and laughter in mourning can be “unbelievably cathartic.”
Research backs the stiletto. Bitterly, Brooks and Schweitzer found that appropriate humor that landed made people seem more confident and competent, appropriate humor that fell flat did little harm, and inappropriate humor lowered perceived status.
The head-of-state test for families
Kal judges a society’s freedom of expression by whether its cartoonists can draw their own head of state. One Egyptian cartoonist told him he could draw Hosni Mubarak any time, “as long as I draw him in a positive light.” Alex asked whether the same applies to families. Can the kids tease Dad about always burning the burgers? Kal’s answer: “Laughter to me is a bond.”
What this means for you: You don’t need to be funny. Start with yourself, aim at situations rather than people, and let the family lead in moments of grief. In family meetings, notice whether anyone can gently tease the patriarch or matriarch. It’s an informal signal of how safe people feel speaking openly.
How can advisors help families stay connected across generations?
Help them build a rhythm rather than waiting for a big event. “Relationships don’t happen,” Kal says. “You have to work at them.” Families drift when they take each other for granted, so he recommends scheduling regular contact, such as a monthly video call with all the cousins. Nor does anyone need a reason to call. “You don’t need to have anything to talk about,” Kal says. When Alex suggested calling someone just to say “I was just thinking about you,” Kal called those “magic words.”
What this means for you: In reviews, ask how often the whole family connects outside holidays and money matters. The same principle applies to your relationships with clients’ adult children: check-ins that ask for nothing build a different kind of trust from a meeting invitation.
Share with your clients: Set up a monthly family video call. Keep it short, invite everyone, and let quieter relatives simply listen in.
How do you bring these ideas into client meetings?
Make them small, repeatable parts of the relationship rather than a one-off project.
Ask legacy-first questions. “What would you tell your 25-year-old self?” opens a different conversation from “Who are your beneficiaries?” Kal would tell his younger self he was “sweating too much.” Or try: “Which qualities do you hope your children say they learned from you?” Kal’s own list was being honest, straightforward, hardworking, kind to friends and generous.
Add an archive question to annual reviews. “If something happened tomorrow, who in your family could tell the story behind these photos, this collection or this house?”
Give stories a place to live. Total Family’s platform keeps legacy letters, purpose statements and milestone records together with the context that makes them meaningful.
Use humor on yourself first. A self-deprecating line is the lowest-risk way to lighten a heavy meeting.
Frequently asked questions
How can advisors start legacy conversations with reluctant clients?
Lower the stakes. Offer something to react to, such as a sample purpose statement or a short letter prompt, then ask what they’d change. Their edits reveal their values.
What is a purpose statement in legacy planning?
A purpose statement is a short statement of why a person or family does what they do, a North Star for decisions. In Total Family, clients reach one by answering six questions, choosing a suggested statement, and editing it until it fits.
Do legacy letters replace estate planning documents?
No. Wills and trusts transfer assets. Legacy letters pass on values, stories and context, so they complement the legal plan rather than replace it.
Listen to the Full Episode
The full conversation with Kevin Kallaugher 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.
