Episode Transcript
LAUREN: I'm Lauren Ferrara, journalist and TV anchor turned legacy film producer at Why Wait Stories. I help families capture the stories that are important to them and turn them into a film. So as you can imagine, I love a good conversation, and I love asking questions. And today we're talking about combining financial planning and mental health counseling to transform outcomes for families. In this episode of Purposeful Planning Podcast, the husband and wife team of Sean and Jill Maher share how their interdisciplinary approach transforms outcomes for families and business owners. Our hope is that this conversation will be valuable for fellow advisors, attorneys and family office professionals about how embedding relational connection into the financial planning process leads to more meaningful results. So Sean Maher is a financial planner, and Jill Maher is a clinical mental health counselor. Sean and Jill have a beautiful perspective on why financial planning must include both technical precision and emotional clarity. They also wrote the book The Greatest Gift: 9 Principles for the Transfer of Your Legacy, along with your wealth, which kept me up all night in the best way possible. Jill and Sean, you're I said this just offline, but your book felt like the guide to a good life. So thank you for writing that. Thank you for being here today.
SEAN: Well, thank you for having us and thank you for the compliment. I usually tell people it's a good bedtime story, meaning it will put you to sleep. So
LAUREN: I loved all the really good stories woven in, great advice, and actionable steps that I think I’m going to implement in my own family.
JILL: I love that this is fun, just like it was Sean’s baby—Sean’s kind of brainchild—that evolved naturally out of an experience he had with the family, which I’ll let him share. It was fun to witness and then be able to collaborate with him on this. It was a fun project. Thank you.
LAUREN: I love the word takes. At the end of every chapter, there was still your voice, and it was such an interesting and different take that was so complimentary.
JILL: Thank you. I think it’s an important combination and a little kismet that we bring naturally as a couple.
LAUREN: So, can you describe your purposeful planning journey to us?
SEAN: Well, I’ll start. As you mentioned, I’m a financial planner. I’ve been one for 30 years, and about five years before the book was written, I had an experience where I had been working with a family for 20 years and got really close to the mom and dad, the patriarch and matriarch. Unfortunately, even with the best financial planning, legal structures, and tax structures, when they died, the three children started a war with each other and, to this day, are still not talking to one another. Of course, coming home to Jill and telling her how upset it made me, she said, “You know, you got all the tactical parts right, but you missed the relationship.” I don’t know if Jill said it quite so succinctly, but she suggested that maybe I ought to write it down and journal about it. That really became the genesis of the book. In the process, I was very fortunate to find the Purposeful Planning Institute and all the resources it offers. It became a journey of realizing there are other people in this world feeling the same way, and asking how we can find resources for our clients. That’s really how we got here and how I discovered PPI.
LAUREN: What about you, Jill?
JILL: Yeah, it’s so interesting. I feel like the Purposeful Planning Institute represents what Shawna and I evolved together with our careers—to grow each other and push each other in various ways. I was like, “Oh my gosh, there’s an organization out there already exploring this and navigating this.” It really is what you all are doing—intentional, purposeful, holistic planning. My journey is kind of cool because of my background. I started in business out of college and studied marketing, then went into sales and spent many years in the corporate world. I stayed home with my children for a long time, then went back and got my master’s in mental health. It’s a neat blend because Sean and I can talk business and relate to each other there, and I can bring a new perspective around relational and mental health to what he was already dealing with. That combination really brought us to where we are, along with that experience he had with that family. Lauren, it was so heart-wrenching to watch him grieve for this family and feel so helpless after working so hard to do all this really well-done planning, only to see it still imploding. I was glad we could work through that together.
LAUREN: And you guys, the big takeaway from the book for me was that this is about so much more than money. Can you go into more detail about this family—any amount you’re comfortable with?
SEAN: Yeah. We talk about it in the book, and of course, everyone’s names are changed for confidentiality. Each of the three children received over $50 million in inheritance. Someone might step back and look at that big picture and say, “How could they be upset at all?” But that’s when you realize it’s not about the money. It’s about, “Am I worthy? Am I included? Am I connected?” A lot of this journey of writing the book represented that—it’s so much more than money, to your point.
LAUREN: What do you both see as the biggest missed opportunity in traditional estate or financial planning?
JILL: You want me to start here, Sean?
SEAN: Yes.
JILL: This is your business. I’m so glad that now you aren’t missing this opportunity and that you’re working toward it and spreading the notion that the system is changing. You’re looking at passing on a vehicle—the system, which is the money—yet the system itself, the family, changes with death. There is an incredible opportunity to help families navigate change and loss proactively. Where else are these conversations happening other than estate planning? We typically avoid the topic of death in other arenas, and here financial planners have a great opportunity to do something really helpful and holistic for families—to help them intentionally and proactively navigate a changing system that will happen with death. None of us are getting out of here alive; death is inevitable. So why not begin to normalize and regulate conversations around the topic of death and changing family systems? A healthy family is a major focus now across religious and social institutions, highlighting how important family is. You have access to help families stay healthy and maintain that for generations. I see this as an incredible, meaningful opportunity for planners.
SEAN: Yeah, and when you think about the amount of time spent, as financial advisors, it's easy to talk about wealth, forecast future retirement income, or update your will and estate distribution diagram. But without talking about relationships, that’s the missed opportunity. I like to say, when conflict comes up, I run away. Joe runs to it. We have to be in a position to ask the hard questions and stir up some of the controversy while mom and dad are alive.
LAUREN: Yeah, conflict is inevitable, and you mentioned that in your book. You also used a great analogy—so many of us think about a family tree, but you guys think about a wheel and spokes. Can you explain that a little bit?
SEAN: Sure. That concept comes from;, and we gave them credit. David is one of the founders and very influential in PPI. The idea is, if you think about mom and dad in the middle, everything else spoke out from there. When mom and dad are gone, the glue holding the family together really disappears. You see this pattern repeatedly. Jill mentioned being deliberate about relationships, about roles, and identifying who will do what—not just who will be the trustee or executor, but who will get the family together regularly. If that was dad’s role and he’s gone, who will do it? Being proactive and preparing for that is key.
JILL: I’m going to jump in. What a great, clear explanation of a system. I usually speak in a professional language, but the wheel analogy is perfect—it’s a system. The wheel rolls and is strong because of that setup. Remove the matriarch or patriarch, and the system becomes unstable. You practice a changing system while mom and dad are alive through family meetings. By taking mom or dad out of the leadership role with the financial planner and relational expert, you let the family practice a new system where mom and dad aren’t the middle spoke anymore. This helps the family navigate: What will this look like when they’re gone? What are our roles? How will we communicate? How will we relate to one another in a new way without them present? It’s like practicing.
SEAN: Yeah, and if I can tell a quick story—principle number four of the book is to develop roles. We had an experience where mom and dad were changing their will, and we were involved in some of that conversation. I’m not an attorney, but I sit in on a lot of meetings. Mom and dad chose their second and third children as co-trustees and co-executors. The oldest child got very upset and was on non-speaking terms with his parents for almost a year. That’s healthy conflict. Mom and dad are still living, and everybody’s fine. The oldest son realized he might be too busy to take on this role. But imagine if that conflict happened with mom and dad not in the picture—there would be fighting among the siblings. We encourage families to be deliberate and intentional, to stir these issues up and create consistency and succession while everybody is alive and able to talk to one another.
LAUREN: How do you think advisors benefit from your approach?
SEAN: The depth of relationship is unparalleled. We’re talking to the Purposeful Planning Institute community, so this is somewhat table stakes for this audience. The traditional financial model of “we’ll outperform the firm down the street” is irrelevant. Families are savvy enough that they’re not just looking for traditional wealth advisory or estate planning—they really need and want this holistic approach.
JILL: And it’s multi-generational. You’re building relationships with the next generation in a very intimate way. It’s not just the surface numbers or logistics of planning; it’s about showing that the family is important to us. Of course, that benefits the advisor, because they start relating to the family in a different way.
LAUREN: Love that one big theme, and I hadn't really thought about it until I read the book, but was fear? Talk about the role that fear plays in estate and financial planning. It's a big one.
SEAN: Yeah, and I want to direct you, or listeners, to page 212. There's a great chart that I give Jill all the credit for in the book. And it's really the full summary of how we look at emotions and how those emotions can dictate behavior. And so when, when, when you look at what we call, what I call dis—destructive emotions. Jill will tell you there are no all emotions, maladaptive, maladaptive, maladaptive emotions. But fear, fear of the unknown is what we were attributing to a lot of maladaptive behavior because people don't know. So out of fear, conflict will exist. Principle number nine is over communicate, and with that, we're talking about family meetings, intentional conversation. Fear of the unknown is really what we've seen as a common thread for many conflicts. There's also fear that I don't belong, fear that I'm not enough. If money is tied to love, then fear that I'm not loved if I'm not getting the money that I expect. So it's a complicated emotion, but it shows up quite a bit.
JILL: I'd love to add some brain science here too, because when we're regulated, i.e., we're not afraid, we're regulated, we feel safe. That's when you're in your prefrontal cortex, and that's when you can connect relationally. That's where executive function lives. That's where creative decision-making lives and problem-solving. So as soon as we get afraid or feel unsafe, we move out of that prefrontal cortex, we go back into our prehistoric brain, and we can't access all those great things. So just for the purpose of having effective estate planning, we need to be regulated. We need to not let fear drive the train. And the parents have such a big influence on that, or the matriarch, patriarch, whatever that looks like, because they're the ones that probably created the wealth. So they're going to be more regulated around the wealth. They're going to feel safer around the wealth, so they can actually impact that regulation state with their children. Like, our systems talk to each other. When I'm dysregulated, you'll feel it, and it will spur your nervous system into dysregulation. So it's like a shared state that parents can do by providing that safe, regulated environment.
LAUREN: And of course, we never want to wonder or say the phrase, “Mom and Dad would have wanted the other,” right?
SEAN: Now, I know you read the book.
LAUREN: That phrase—my dad passed away about 10 years ago, and I hear my sister say, “Well, Dad would have…” and sometimes I don’t think so. I mean, mine is so different than yours that that part really resonated for me. So tell us more.
SEAN: About that. Yeah. I mean, it's again just the ability to communicate. Jill and I have been playing around with this with our children. Our children are 27, 25, and 21, and it's uncomfortable. I mean, we wrote a book about it, and it's uncomfortable for us. It is not easy to talk about what happens when we're gone. It's just not something we're wired for.
JILL: We're doing it over Thanksgiving. We're playing the Purposeful Planning Institute suggestion, the Death Deck. Oh, nice. Yes, we're going to play it as a family.
SEAN: And we learned about the Death Deck on the Purposeful Planning podcast. It's just a great resource. All the resources in this community are so helpful to spur on these kinds of conversations.
LAUREN: Well, that leads me very nicely to this question: at what point should parents disclose their net worth to their children?
SEAN: I want to take this one, Jill. I have a client, and it's become a running joke with us now, because all he wants to do is tell his kids and grandkids how much money he's created. And look, he should be proud. He's created a huge estate. He’s reluctant to have a family meeting. Last summer, he called me and said, “All right, we're ready. We're going to do the family meeting, and let's tell the kids about the trust, how much is there, how it can be used, and all the rules and regulations around how the money will be spent.” I said, “No. Stop. Let's talk about values. Let's just do a values meeting, really level setting.” We talk about it in the book: the first family meeting should give everyone an equal voice, practicing talking to one another, engaging in negotiation and conflict resolution around a simple topic, which is: what are our family values? I explained that to him, and he said, “Okay, great, and at the end, we'll tell him about the trust and all the money.” I said, “No. We're talking about values. We'll get to that, but first we need this first family meeting.” So, you'll know when the time is right to tell your kids about money. But let's not make it about the money. Let's put that in the backseat so the emphasis is on connection and family values first, then we can talk about the money.
JILL: What a great highlight example of that. Someone had an agenda. He had an agenda with the family meeting of wanting to share that amount because he was so proud, which is not a bad thing. But if we lead with that agenda, the focus of the meeting becomes all about the money. There's no hard answer at what point or what age—it could be anywhere from 12 to 21 depending on the family, the children, and their ability to process and talk about money. I would say start with you first, as the matriarch or patriarch. What’s your state about sharing that? Why are you wanting to, and why are you hesitant? Explore where you are with it, because you're the leader. The whole regulation piece and the no-agenda piece start with: where am I with my views on money and what motivates me either way? The healthier and more aware you are, the more you will pass that on to your children and the way they navigate it.
LAUREN: But you also don't want it to be a surprise at the end, right? Estate planning shouldn't be a surprise.
SEAN: Right. I love doing this sort of informal poll. It's part of the first family meeting when Jill, I, and the rest of the team host these meetings. Jill, along with three of her other counselor colleagues, are now regularly involved with our family meetings. So we have four counselors on call, so to speak. The first thing we do is a “views on wealth” survey up front: how do you view money? One of the questions is, “I view myself as lower class, middle class, upper class.” Within the same family, you have different expectations, which illustrates the point you made about not wanting surprises. Most people expect they’re going to inherit either more or less than the actual number. If you're expecting 10 million and you get 8, you're going to be upset. But $8 million is a lot of money.
JILL: Yeah, clearly you definitely want to talk about it. It's just not necessarily leading with it. It's setting a foundation to talk about what naturally people are going to gravitate to, which is how much, how much?
LAUREN: Well, let's talk about how charity factors into these conversations. And would you consider charity a meaningful part of family relationships? I already know the answer to that question.
SEAN: Well, yes, you're right, and it's one of the principles. I want to be careful because not everyone's charitable, and I've learned this over the years talking to families. A lot of people say, “Charity begins at home. I am not interested in giving to nonprofits,” which I respect—people have different views. But charity serves a couple of different purposes that we write about. One is to develop a common purpose, which is principle number one—the idea of having a reason, a purpose for everyone to get together on a regular basis to talk about charities that can be benefited along the way. The other purpose for charitable family work is just the education that comes with it. I love the idea of young people learning about rate of return, markets, asset allocation, all the things that happen in investment meetings when you're talking about maybe a donor-advised fund or a family foundation, where the risks are really low. It's not about me; it's about this fund that's been put together so that when they're in their 20s and 30s and starting to deal with their own wealth, they've got a foundation of experience. These aren't new terms or new concepts.
JILL: I'm going to jump in too with another motivator, which might encourage some of these families—who, I respect, aren't interested in charity—to consider it once again and revisit it. It's a great way to create an association for a family. When you do charity work, it produces serotonin—brain science. It literally releases that serotonin chemical. Serotonin is your primary component of antidepressants. It's the contentment chemical; it's the feel-good satisfaction chemical of our brain. So when you give charitably, and this isn't theory, this is proven now with PET scans—whether it's with your time, your talent, or your resources—it produces serotonin in the brain. If the family is doing charitable work around the estate, money, and death, there's a whole association that starts happening of calm, contentment, and connection around these topics. You're kind of doing a little backdoor way of associating death and money in a positive way through charity. So you don't have that natural reaction that happens when grief takes hold or money is being discussed—that protective, dysregulated response. You've actually created an environment where serotonin is associated with it, so I like it as a little backdoor way to rethink death.
LAUREN: Yeah, and you guys also described it as the antidote to entitlement, and I thought that was—but another thing that jumped out to me in the book was transformative tourism, I think, are the words you use, where there was somebody who went to Costa Rica, spent a year there, and then the awe of her family's wealth and the appreciation of what she could do with it was pretty interesting.
SEAN: Yeah, and we've experienced that with our children as well. Fortunately, they've each had an opportunity in high school in those really formative years around money and identity, understanding—sorry.
JILL: About you, identity, money, and identity, yeah, yeah.
SEAN: And the transformation that happens when they get back. One of our sons broke down crying when he pulled into the garage and said, “This is bigger than some of the homes where I visited, and this is where we were keeping our cars.” It really affected us as well as it did their perspective.
LAUREN: Yeah, we started a couple of years ago doing this in my own family. We spend a month in a different country every year. We've done Mexico City, and we spent a lot of time in Guatemala this past year. My kids are young, so I don’t really expect that they think, “Man, we have it so good.” But just for them to know there are places in the world where they don’t have access to clean water—it really changes their perspective.
JILL: Yes, yes. Gratitude and perspective go a long way.
LAUREN: So what tools can you suggest for advisors to create an environment that prioritizes trust, candor, and emotional safety, especially in these multi-generational settings?
SEAN: Jill, your favorite—curiosity. Go.
JILL: Wow. So, I mean, the greatest tool is the family meeting. Just having the meeting and leading with curiosity is one of my favorite taglines. Starting with questions with a family about their views on wealth: what is your perspective, what would be a healthy inheritance, what are you hoping for, what are your concerns and fears—all that curiosity. Because what you're setting in that environment is: you matter, I'm curious about you, it's safe to have an opinion, and it's okay. We're going to communicate about difficult things. Leading with curiosity shifts the whole conversation and approach versus telling, teaching, or designating how money is to be used. Having these meetings with mom and dad alive, that whole regulation piece we talked about, makes it safe for everyone to have these conversations. I say, use the stability of the system while the parents are there.
LAUREN: What percentage of families—family meetings make so much sense. Do most families actually have these, or is that first one kind of awkward, like, “Hey, don’t have a family meeting?”
SEAN: Yeah, that's a great question, and it's really hard. Since the book came out earlier this year, we've really been talking about it at every meeting as a firm. We have 12 reps, and we're talking to families all the time. It's hard. People say, “Oh, that's great. We'll do that someday.” But pinning them down to a date is very difficult. Unfortunately, two weeks ago, Mother was diagnosed with terminal breast cancer. They rallied and said, “Let's get a meeting together.” We booked it four weeks out; she died three weeks later, the week before the meeting was to occur. That’s the inspiration for me—to just get people to the table. Everybody's nervous. We shared that story in the book: even Jill and I, when we have that with our children, are nervous. The kids are all nervous. They're asking, “Who's dying? What bad news are you about to tell us?” It’s not that. It's just getting everyone around the table. It’s an insightful question: how many families are actually doing it? It's hard, but families appreciate that we're bringing it to their attention. The second or third time you ask, they take out their calendar and say, “Alright, let's get serious about this.” And a lot of these meetings happen around Thanksgiving, the Christmas holiday season. We have one family that meets every Fourth of July. Those are natural times when families get together, and we say, “Look, we just need three hours. Carve out three hours. We promise it will be worthwhile.”
LAUREN: You're speaking my language because I have those similar experiences in what I do in legacy films. I've had so many heartbreaking conversations. By the time families call me, it's usually because Dad's not feeling well, and we talk about a legacy. So often, painfully often, the next time I get the call is, “Oh, we're interested, maybe later,” and then Dad passes away.
SEAN: So that's interesting. You experienced the same thing. People say, “Oh, that's a great idea,” but it's often too late. And yeah, I just have to stay ahead of it.
LAUREN: Yeah. So you also talk a lot about, and I think this is one of your principles, about sharing your story—sharing this story, the origin story, the story of the wealth. Share a little more about that.
JILL: You were reading my mind, because as you brought up your legacy films, I thought, that's exactly what you were doing. It's exactly one of the principles and such a great resource for us to incorporate into the family meeting. But go ahead. Sean, what was it?
SEAN: Two things. With each principle, we have a proposition. The proposition is that perspective grounds you. When you share your story, you give perspective, and perspective grounds the person who's receiving it. We write about a client who is a complete workaholic. He's never around, and he shared with me in a very vulnerable time that he has this huge fear around money and not having enough. I asked him, “Have you ever told your kids?” He started bawling. He just started crying, saying they don't know. They just know that I work really hard. It was freeing for him to share his story with his children about his upbringing and the scarcity of money when he was younger, to give them a perspective that it's not that Dad doesn't love them or that he's not around; it's that he has this fear he's working on and trying to get over. That's one perspective. The other perspective is that inheritors often come with guilt. They inherit these huge sums of money, and they don't really know where it came from. There's this suspicion that maybe it's dark money or there was some sort of impropriety along the way that created it. Knowing the family story—how it came about—is really important to create that perspective.
JILL: I'm also hearing you're creating meaning—there's meaning behind the money. So it's not just a number being passed on. It's Mom and Dad's blood, sweat, and tears, their struggles, their sacrifices. It puts so much more meaning into it, and therefore the inheritors probably approach the money differently because they have more compassion for the story behind it and the sense of belonging that's created. There's modeling of failures and struggles that you're providing for your kids. There's so much benefit beyond just the financial and planning aspects. As I'm sure you found in your business, it's really healthy for a family.
LAUREN: It's very healing, I would describe. I don't think people watch these films together and realize that that's going to happen. But so many good conversations happen after the viewing.
SEAN: Yeah, that's great. It's just true.
LAUREN: So what is one mindset shift you'd recommend to advisors who want to start integrating these ideas but aren't sure where to begin?
JILL: I would suggest don't look at it as all or none. It doesn't have to be all or none. Things start small. You can simply encourage the topic and lead with curiosity, bringing five or six questions that might pertain to the family to open up and begin discussing a deeper viewpoint or perspective about wealth and money. That's my suggestion. Sean, I'm curious to hear from your vantage point.
SEAN: I agree—start small. Find resources. If you're part of PPI, there are plenty of people that can help with these kinds of things. I struck gold by marrying Jill in a lot of ways. Having a partner who's also available to bring this type of guidance to families is just so easy. But there are plenty of other firms, counselors, and professional facilitators that can help with this. If you're wired for rates of return and financial advising in the traditional sense, partner up with somebody.
LAUREN: So what's a moment you'll never forget when this work made a difference—not just in planning, but in a family's life?
JILL: You want me to go, Sean? Tell them. Yeah, I left one of these meetings with a co-worker of Sean's, and he turned to me and said, “I've been working with this family for 12 years, and I have never known them so well as I do now, and been more confident with asking them to participate in private equity, asking them this or that, because it's deeper, it's more holistic, it's more relational.” He's like, “That really shifted the way I'm relating to this family.” I was like, “Wow, that's really cool.”
SEAN: Yeah, the story I love talking about is this: we can meet for three hours, four hours, five hours—it doesn't matter. The last half hour is always the most significant, at least in this one particular case. Jill and I and one of my colleagues did a values meeting with a family. Three hours in, we had some other content, and as we were wrapping up, the patriarch said, “There's one more thing.” You hear about this doorknob confession when you're with a therapist: as you're leaving, you grab the door and say, “Oh yeah, one more thing.” It's sort of the same concept. The patriarch looked to his daughter and said, “I want you to run the company.” The daughter had at one time worked at the company, she's now raising their children, and her husband works at the company. She started crying and bawling. The emotions just couldn't be covered up. This was a conversation he'd been holding on to for probably two years. He was tired, wanted out—he either had to find his successor naturally in the business or sell the company. Without this family meeting, I don't know how much longer it would have stayed bottled up. Now they're working on succession and identifying the people in the company who can take over. It was really meaningful and unexpected in a lot of ways.
LAUREN: You guys definitely keep people from being a Dateline episode or the next season of Succession. I took that from your book—such a funny line. This has been such a great conversation. We are so lucky to have your perspective here at PPI. My big takeaway is it's about so much more than money. You guys talk about trust, love, and belonging, and I love it. So thank you, Sean and Jill.
SEAN and JILL: Thank you for having us.
JILL: So fun, so fun.
