S1:E30 | Estate Planning as a Doorway to Family Healing

Guest Speaker(s): Catherine Hammond, President, Hammond Law Group, PC
Host: John A. Warnick, Esq., Founder, Purposeful Planning Institute


Explore the profound connection between estate planning and family healing in this thought-provoking podcast. Join us as we delve into the significance of estate planning as a catalyst for addressing generational challenges within families. From navigating difficult conversations to fostering healthier relationships across generations, discover how estate planning serves as a doorway to healing familial wounds. Whether you’re a baby boomer seeking tools for bridging the gap with younger generations or a professional aiming to integrate family healing into your practice, this podcast offers invaluable insights into leveraging assets and businesses for the greater good of family harmony. Tune in to unlock the transformative potential of estate planning in fostering familial connections and building a legacy of understanding and unity.



Catherine Hammond is an award-winning attorney, life transition guide, and the author of Hope-less: The truth about hope and where to find it. The experiencing of multiple devastating crises brought her to understand the true nature of hope and dedicate her life to supporting others through the ups and downs of real life. Today Catherine’s primary focus is helping individuals, families, and executive teams navigate challenges and thresholds of all kinds. Mother of two, and “Mimi” to four precious grandchildren, when she’s not spending time with her husband and other loved ones you’ll find Catherine hiking near her Colorado home, traveling, or writing her next book.

JOHN A: Good day, everyone. This is John A. Warnick, founder of the Purposeful Planning Institute and your host today for this Purposeful Planning Podcast. Our guest today is Catherine Hammond with the Hammond Law Group, and the title of today’s conversation is going to be estate planning as a doorway to family healing. And this is really a result of a conversation I had a year ago with Catherine. We’ve been delaying a lot of stuff going on in both of our lives but we’re here now. And the conversation was magical a year ago, as I discovered the tremendous heart that this woman has, and the way in which she views estate planning as really a pathway or a doorway, as we’re calling it, in the title to family healing. And I would say, Catherine, just as a further introduction, that this topic of reconciliation, a strange moment, family fracturing, it’s been weighing deeply on my heart and my mind for at least three or four, maybe five or six weeks now. And I’m trying to make sense of it. And I think this conversation today will provide hope, and some new insights for both me and for everyone listening with us. It is our tradition in these podcasts to ask our guests if they would share what we call their purposeful Odyssey, the story of how you’ve arrived where you are today. You can make that both professional and personal both. But we’d love to hear if you could give us a two to three minute purposeful Odyssey, that’d be awesome.

CATHERINE: John A, it is such a pleasure to be in your presence always. I’ll start by sharing I think a mixture of the personal and professional things that brought me to where I am at this moment in life and in my professional world. I grew up as the daughter of a single mom who was clinically and suicidally depressed. And that obviously has a huge impact on how we come to see the world. With my mother, her depression eventually morphed into Alzheimer’s disease. And when I was a teenager, she was put on disability from her job as a Special Ed teacher when I was 22. She was no longer able to live on her own. And so I had to start the process of setting up a conservatorship and guardianship. And I was lost, it was overwhelming. And I happened to be referred to one of the lawyers who was a founder of the Elder Law Movement. We were living in Denver at the time, she held my hand and walked me through that process of taking care of my mom at the initial stages. And the way that she held my hand and guided me through that really overwhelming and that tragic situation was my inspiration for going to law school. I wanted to help other people navigate the legal system, in the event of incapacity and at the time of death. And so I went to law school and became a lawyer. My journey went in different directions. And eventually 19 years ago, I ended up starting my own estate planning and elder law firm Hammond Law Group. And what I discovered was number one, that we don’t always have to go through the legal system in the event of incapacity and at the time of death. So I became passionate about educating my clients and helping them meet their goals in terms of making things as easy as possible. But the longer I have practiced, the more I started to see the unique position that I am in and that we are in as trusted advisors. When we are invited into a family’s world, as I am when I’m invited in for an estate planning conversation. When I sit down with a couple and you mentioned estrangement, and that’s something that I know we touched on in our original conversation. And that is just heartbreaking to see the way that that happens through the generations and the impact that has both on, if it’s a parent and child estrangement, both on the parent and on the child, on the grandchildren, and that carries through the generations. And so I have been looking for ways over the years to serve my clients more and more deeply. And because I’m also trained as a coach, and work as a coach, I have brought coaching into my law practice. And it’s been very interesting and exciting to see the ways that we can, in a regular old initial estate planning conversation, open up the door that the clients have opened for us even more widely, to touch on the things that will have a lasting impact for them, and for their family.

JOHN A: Beautiful. I couldn’t have asked for a better purposeful Odyssey story to launch this conversation. You captured so much there. I’ve heard you say, Catherine, that true wealth is what you have when all the money’s gone. I remember that I used to surprise clients in an estate planning design conversation by asking them, “Now, in what currency do you want your estate plan denominated at?” And this was back in a period when the dollar was in a freefall and a lot of people would go, “Well, I still believe in the US dollar not Swiss francs.” And I would turn that around and help them understand that I wasn’t talking about financial currency, I was talking about emotional currency. And so as you point out, our clients when they come to us for estate planning conversations really are opening a door. And another point I just want to affirm, I think it’s marvelous that Catherine has obtained coaching credentials, and that she’s applying those in practice. That’s lawyers, CPAs, CFPs, all of you who are working on the technical side, please pay attention to Ctherine’s example. But Catherine, I’m going off too far here. Let me take you back to help us understand what you mean, when you say, “True wealth is what you have when all the money’s gone?”

CATHERINE: The center of the Purposeful Planning Institute and all of your work, that the money will only get us so far. And just in terms of even if it’s managed incredibly well, over the generations, you can leave a large chunk of money, but just by virtue of dissolution and dilution, as it goes through the generations, there’s going to come a point where there isn’t any meaningful amount of money left for almost every single family. And in those moments, we have to remember that our true wealth is who we are. It’s our beliefs, it’s our values, it’s our wisdom, it’s our attitudes, it’s our stories, it’s our practices, our rituals, the things that we do in our family, that’s our real legacy. And most of us aren’t looking to leave our children and grandchildren enough money that they can just sit back and do nothing. This side of your legacy, the emotional legacy becomes even more important if we want anybody to have a satisfying and fulfilling life down the generational lines.

JOHN A: I’ve got to believe that intergenerational wholeness, did I get it?

CATHERINE: That’s right.

JOHN A: Okay, I have to believe that intergenerational wholeness is really the essence of this emotional legacy. Or maybe we’d say that the result of the emphasis someone would place on creating an emotional legacy. So I think you’re unique and I’d like to think that most, if not all, of the members of the Purposeful Planning Institute are similarly unique no matter what their professions. You’re unique in terms of the mindset that you bring to working with families around legacy. And tell us a little bit about your thoughts on leaving financial legacies, be they large or small. How do you kind of help clients understand the connection between emotional legacy and financial legacy?

CATHERINE: There are some specific exercises that I use to help clients look at those things. One of them is a life map. And this is not for every client who walks in the door to do estate planning. But for those who are interested in going more deeply, we use a life map to map out the major highs and lows of their lifetimes and see the threads through those years, see what are the themes, what are the core values that have carried you through, and use that to starting to think through when it comes to your grandchildren or your great grandchildren, what is it you most want them to have received from you apart from the money and have you left that yet? Because most people don’t think about the fact that in addition to whatever financial legacy you’re leaving, you are leaving an emotional legacy. We have a responsibility to do that intentionally but most people just never think about it. And the thing that I have seen, I just had a client who has an estranged child. And I invited this client to write a letter to this estranged and soon to be disinherited child, letting her know why she was being disinherited. And my challenge to her was to only do that in a positive way, from a place of love and healing, what is the thread of love and healing that you can pass on in writing, because the written word is so powerful. And she started to write the letter very enthusiastically right after we had the conversation. And then a month later, she said, “I haven’t been able to finish that letter because all I can think about are my disappointments and my failed expectations and all of the things that my daughter has done wrong.” And what she wanted to do in that moment was pushed daughter farther away, when in fact, to what most of us need our deepest longing in the world is to belong. And being able to step back and see where this daughter fits in the family story, because she belongs in the family, no matter what road she has traveled now, as an adult, she belongs in the family. And bringing back that our sense of belonging in the world, comes largely from our parents and our family of origin, but also from our grandparents and our great grandparents, and we don’t typically think about those things. I had lunch with a client yesterday who was talking about how his father served in World War Two, and that completely defined who he was as a father, his horrible experience in World War Two and the Battle of the Bulge, and he never spoke about it. But he carried it and he carried it to his children who then passed it to their children without having ever really processed it. And so, the importance of doing this intentionally rather than haphazardly on the emotional side, as well as the financial side is really really deep. It’s a deep responsibility. I believe that we have as humans, if what we want to do is create more intergenerational wholeness for the coming generations.

JOHN A: I’m inspired by these conversations you’ve been having with clients. I love this idea of starting the conversation in introducing the life map and this concept of belonging. So powerful, Catherine, thank you for sharing that. And I get the disappointment, the heartache that your client was experiencing, and understand that she was having trouble writing a letter that was entirely positive. But so important what you were trying to help her come to the realization that everyone belongs. And we should never exclude what we want to accept. I also am inspired by, I’m going to call this professional shouting. It’s kind of a proclamation that I hear from Catherine that we as advisors, and I want the advisors and consultants who are listening to today’s podcast, to understand that this applies across all the disciplines and professions. But you really have a vision, Catherine, for the deeper impact that advisors consultants can have and working with families, and that that impact can potentially be transformative, and can affect generations. Could you share a little bit more on that?

CATHERINE: I have seen it. I’m thinking of a client who came in and was talking about her estrangement from one of her sons completely and partially estranged from another son and estranged from one set of grandkids. And as we were talking, she wished to hear about some of the things that she had said to them in specific situations, and told me stories. And as I was listening to these stories, and the things that she said, I was cringing, I felt myself, my body contracting and feeling terrible. And I finally asked her, “May I share a little feedback with you?” And she said, “Okay.” And I said, “You’ve shared some things with me that you’ve said to your children and grandchildren. And honestly, if I were in their position, I would feel very judged, and criticized if you said those things to me.” And she said, “Well, good. That’s how I want them to feel.” And she was older and I don’t know where this question came from. But I ended up asking her now, “Is that how you want them to feel even after you’re gone or is that just while you’re alive?” And she said, “It’s just while I’m alive. I want them to learn how to behave.” And that’s the old model of parenting and so that was the inspiration for me. And we have an annual maintenance program for our clients, it’s optional. And so in the annual maintenance program, we offer monthly education, and probably half of those are more substantive. And half of those are more on the coachee side of things. And so I did a workshop that you and I had talked about early last year. I did a workshop last July. And I called it how to enhance your relationships with your adult children on the theme that I had seen from this client, because she clearly had no sense of boundaries. And she was doing what she thought her job as a parent was, and she was doing it very well. And there were a lot of folks in previous generations who were taught and even still today that judging and criticizing your children into proper behavior is the way to do it. So I had this class on enhancing your relationships, which my secret name for it was boundaries for boomers. And I took it easy on them. I offered just a few insights and a few suggestions. And two months later, at the class that I was teaching then, one of my clients came up to me afterwards and said, “I have to tell you, Catherine, that class two months ago, completely changed our relationship with our son. You taught me how to zip my mouth.” He came home with this new laundry hamper. Son’s wife has passed away. Son is living at home in their basement, trying to get his life back together after having it completely blown up by the loss of his spouse. So they’re trying to navigate this together. And he went out and he bought a new laundry hamper. And she said, “When he came home with this new laundry hamper, he was all excited about it. And I wanted to say, that is the stupidest thing ever for you to be spending your money on laundry hampers, we already have a laundry hamper. And I thought of you and what you said, and I closed my mouth. And he was so excited to share the laundry hamper with me. And that has happened over and over and over again.” We get these moments with our clients and they are precious precious gifts. And we have the opportunity to point people towards what we all want. Most of us would love to pass money to our children and grandchildren. But what we want more than that is to pass emotional well-being and wholeness to them, and we get to be part of that as trusted advisors.

JOHN A: It’s such a privilege. And I kind of humorously tell people that I’m a recovering tax attorney. But I’m really inspired as I listened to you, Catherine, to reframe that and say I’m a peacemaker. This opportunity, it’s just these are fabulous. Your question about how to tell the client, the woman that, “Is this what you want them to remember you by now or after you’re gone?” That question is so powerful. And what you’ve done here with the coaching, broke the maintenance program and the influence you had on this woman and her son to change their relationship, it’s just inspiring. So I’d love to have you close, by helping us understand how we become aware, how we help our clients become aware of what family legacy is, and that it isn’t just something we pay lip service to, but it requires some work. So could you kind of share maybe this metaphor of legacy as a garden? I love the power of that metaphor.

CATHERINE: Yes. I’ll say I think it starts with us, it has to start with us. And I am in the middle of this myself, I have two adult daughters, they both have children, they both have spouses. And we’re in it in the same ways that any family is in it in terms of working out the things that need to be worked out in our family, it starts with us, and then we can bring it to clients. So we have to be brave enough to start exploring these things ourselves. But I see it as a garden. And so we can choose what in our family legacy, what we inherited, we want to fertilize and help grow and what that we inherited, and what that we’ve cultivated up until now in our lives. We want to cut back and weed out. And so in my world, this means it’s helpful to look back over our own lives, and see where we have been and the themes in our own stories. But it’s also helpful for those who are brave enough to look back another generation or two, at the stories that built our parents and our grandparents because those are also the stories that built us. So we are seeing where our ancestors have been where we have been. We know where we belong. There’s a deep sense of belonging that comes from knowing our grandparents. And in seeing all of this, we can see where we want to pivot, where do we want to cultivate, where do we want to weed, and that’s how we move towards intergenerational homeless and passing on the things that we rather than just by default, passing on what we were given, passing on intentionally with words that last forever. When we’re born, I think most of us feel a great sense of freedom as tiny infants, and then life happens and we start to feel all of this darkness and heaviness and then life is about moving kind of on a spectrum like a scale from that darkness and heaviness through liberation and into freedom. And we, as grandparents or future grandparents, have the ability with our own processing and integrating and our words, to help our descendants push a little bit farther, stirred out a little bit farther on that spectrum of darkness into freedom by knowing who they are. And by cultivating and cutting out some of the weeds so that the weeds don’t have to be quite as weedy for the next generation.

JOHN A: As you’ve been sharing these thoughts with us, Catherine, I’ve been thinking of a law office, it could be the conference room in a financial management firm, but having pictures of beautiful gardens. It just to inspire people to understand that legacy really is a garden, and the choices that they make on both the fertilizing, the planting, the nurturing, and then the weeding, and cultivating and has to be done, all of these intentional choices will eventually result in something as beautiful as the inspiring picture of a garden. This has been truly inspirational. And you’ve helped bring a precious bone to me, because I’ve been carrying this heaviness worry. I have one client situation right now, where a father and son are deeply estranged, and it is getting worse, not better, despite my efforts. And I would just say, “Let’s never give up. Let’s always carry the hope.” And be willing to ask the courageous questions and put the promising metaphors that, Catherine, has shared through her actual experiences with the clients today. I can’t thank you enough for this. It’s been wonderful, Catherine.

CATHERINE: Thank you so much for having me. And if I could leave you with anything, if I could leave your client with anything, if I could leave your listeners with anything, it would be just a starting place: have a very simple exercise, take a piece of paper, draw a line down the middle, and on one side, write down where my family is complete, and on the other side, right down where my family is not yet complete. Where are we whole and complete? Where are we not yet whole and complete? Just to start to take inventory and see where it is that needs some fertilizer in your life and your family. 

JOHN A: Well, what a wonderful way to end this podcast with that suggestion. Thank you, Catherine. And thank you everyone for listening.

CATHERINE: Thank you.

Subscribe Now!

A Better Way, A Better Process, A Better Practice Is Within Reach!

A Supportive Community & Tools You Need

Thought Leader & Industry Innovator Webinars

Purposeful Planning Resource Center

Online Directory of PPI Members

And So Much More, Don't Miss Out!