Breaking the Pattern: How Self-Awareness and Choice Transform Family Wealth Dynamics

Welcome to Legacy Builders, strategies for building successful family enterprises. Brought to you by Beacon Family Office at Assante Financial Management Limited. I’m your host, Cory Gagnon, Senior Wealth Advisor. And on this show, we explore global ideas, concepts, and models that help family enterprises better navigate the complexities of family wealth.

Today, we welcome Kristen Heaney, Founder & Coach of In Three Generations, LLC. With a deep understanding of family wealth challenges, Kristen has established herself as a unique voice in the wealth management space. Her authentic approach as an “unprepared inheritor in recovery” has made her a trusted advisor to financially successful families navigating the complexities of wealth preservation and transition. As both coach and consultant, Kristen focuses on bridging the gap between the gratitude of wealth and its inherent burdens, particularly through her practical work helping families implement effective strategies while supporting professional advisors in connecting with their clients’ complete family dynamics.

My goal is to be the most curious person in today’s conversation with Kristen, where we explore her insights on listening to life’s patterns and breaking free from unconscious behaviours. Our discussion focuses on how wealthy families can honour their legacy while allowing individual expression, particularly for the rising generation navigating stewardship responsibilities. We’ll examine how families can redefine success, create role clarity, and build governance frameworks that balance collective purpose with personal autonomy.

Now, let’s dive in!

Cory: Welcome, Kristen. We’re excited to have you here today to share your wealth of knowledge and experiences with us. Let’s dive in, shall we?

Kristen: Thank you, Cory. I’m so excited to be here.

Cory: Kristen, imagine you’re delivering the commencement speech to the graduating class of 2025, and you have the chance to inspire them with your story. How would you begin your speech to convey the incredible lessons and expertise that you’ve gained along your career?

Kristen: That’s a big question. And I have my youngest graduating from high school this year. So it sort of is hitting close to home, and hopefully your listeners are going to have ears open to hear whatever this is, because they think that we really can be inspired by those moments when a transition is happening, like graduation. And I think all of us have the opportunity to really think seriously about our lives. And my advice, I think, would be just that, to listen to your life. And if you really pay attention to the themes that are emerging in any chapter of your life, I think what I’ve noticed is you’ll find that those lessons are lessons that you’re going to need in the next phase of your life.

So as I look back upon both, I’m a unique person where the personal and professional parts of my life have sort of merged together. And so it’s very clear to me how if you’re listening to your life, and I think especially if you’re listening to the challenging parts and the lessons learned within that, Life is just much more of a fun ride. Life has much more meaning, and more opportunity for you to bring the fullness of yourself to the next thing that you’re moving into. 

Shared the story before, but for me, that was having lost my dad while I was still in college. Certainly, one of the most challenging things that I’ve been through. But I’ve been able to take the challenges that I experienced moving through that to help other people who are going through similar situations. But really more than anything, it’s less about me telling other people how to get through their life like I got through mine, and more about the fact that it builds the passion and the motivation for me to do the work that I’m doing, and to do it in the in the way that I’m doing it. I think it builds empathy for other people and the situations that they’re in. And so I think my advice would be to listen to your life. Because if you move through on autopilot, you miss the magic that’s there, and you’ll miss the beautiful lessons that life is meant to teach you for the next chapter that you’re moving into.

Cory: I love that autopilot. So many people are in autopilot. And thinking about that, listening to your life, how do you recommend people do that? There’s a lot of spiritual and religious ways that people maybe would associate with that recommendation, and it might be that. But how do you think of that when you think of really listening?

Kristen: I think it requires some introspection. And maybe, you know, I don’t know. You think introspection, you put yourself right into, I don’t know, therapy on a couch or meditation. What I’m talking about is taking sort of an objective narrator’s perspective on your life. Like, if you could watch your own life on a Netflix show, what types of things would you be noticing from the external that maybe it’s difficult to notice from your own internal experience? So watching the patterns that are emerging. Do you keep making the same mistake over and over again? The term I use for it is sacred serendipity. Is there something that is a ridiculous coincidence that just happened that is more than a ridiculous coincidence? It’s a lesson that life, God, you know, whatever, is trying to teach you.

Number one, I also say learn that lesson. Otherwise, you’re going to keep bumping into it. And I also think it’s worth getting curious about what is behind that. What is the force behind that? Because if you’re really listening to your life, it’s pretty remarkable, and I think can make you feel there’s something comforting, to know that your life is starting to feel like a story, and that parts of the story are coming together. It’s a really beautiful thing. And in the times of my life when that has happened, it leaves you with a sense of awe and also helps you to feel like it all sort of makes sense, especially in the moments that it doesn’t make sense.

Cory: Right! And so in some of the work that you do and the lives that you get to witness, those lessons where people keep bumping into things. You made that comment, and sometimes people don’t see it even if they’re being smacked in the face. So what are some of those things that you see where people finally get that this is actually that recurring theme or pattern that you talked about?

Kristen: I think coaching is a space where people often have that moment, because coaching can be an opportunity to have someone else reflecting back to you the story of your life. And so it does hold up a mirror. I mean, counseling does the same. To be frank, sometimes a really good friend who’s a good reflective listener can do the same. But getting yourself into a space where you can see yourself and your life in a mirror because you have that person going, “that’s interesting.”

Now that I think about it, you were dealing with the same situation last year, and I noticed that you handled it this way or whatever. So I think the opportunity for people to have some space in their life where they can get objective feedback, where they can look into a mirror. Sometimes it’s taking a course, taking an assessment, or reading a book. But to make that space intentionally, it is so easy to lose five years of your life on autopilot, and time just goes by so quickly. And to miss those lessons learned by not having intentionally added something in your life to put that mirror up, I think, is where it ends up happening. And I think it can feel a bit exhausting to always be in developmental mode and needing to grow yourself. Maybe there’s a space where that sort of becomes an addiction of itself. But I also think that it takes intention, and it takes courage to put yourself in those spaces.

Cory: And so when you think of that addiction, and oftentimes and you made mention of that five year period. And sometimes it’s a longer period. Sometimes people look back and say, wow, where did those twenty years go? But if you think about that concept, where is that flip? Where do you see people really say, wow, this coaching or this introspection that I’m doing, this feeling that I really now understand my life or understand more about myself. Where do you see that switch?

Kristen: I almost feel like it starts before a person gets into that kind of a relationship, you know, coaching or what have you, because there was a reason that they signed on to do that. So it’s always kind of standard thought that a person changes whenever the pain of staying where they are exceeds the pain of changing, because we all like homeostasis. So I think that there’s something about whatever the precipitating moment is that makes you connect to a coach, or makes you call a friend to say, like, “hey, can you talk me through this?” That is an important moment.

And I also think that the move into getting beyond the present moment, into thinking about your life as a story, incorporating the past and the future and not just being stuck in the every, I mean, we hear a lot about the importance of presence, and being present in the present moment, but I also think that there’s something to be said for seeing the story of your life and the trajectory that you’re on. And so I think that is the sort of, like, getting meta about your life that when you can shift into thinking that your life is not whatever’s going on this week, and the stress of the day, and whatever problems that you’re in, if you flip into that, like, when I’m on my deathbed, does this actually matter? Or in the whole trajectory of my entire story, this is just one page, and I can see the broader future. I think when you can move out of the present moment to begin thinking that way, that’s also an important shift.

Cory: Absolutely! And so as you talk about that narration of the story of one person’s life, when we think of families of wealth, sometimes that rising gen maybe feels like their story is being told for them, or their story, maybe that plot line has already been developed, and they feel that pressure. How do you find that people can get that freedom? How can we help, and how do you help people find that freedom in their story?

Kristen: There’s insight even in your question, and I think that that is similar. So what we were just talking about is an individual sort of being stuck in the present moment and the limitations of that, sort of not seeing your life as a full story. And I think that families get caught into the same trap. And that’s what you’re describing there where the decisions that they’re making, and the approaches that they’re taking in in their decision making are really focused around the present generation, not mindful of the needs of the next generation, their iteration of the family enterprise being quite different.

And so it’s interesting to me how, you know, especially for those who are functioning in a family business, they can easily make decisions regarding their business thinking ten years ahead with regard to innovation of the product that they’re selling or what have you. But when it comes to their own family governance, that’s much more difficult for them to say, how can we be making decisions today mindful of when, you know, these cousins, it’s not siblings anymore. It’s cousins who are making the decision. And so it’ll be quite different because, gee, there’s 27 of them. That seems to be much more difficult for them to see the whole story and trajectory of their family’s life than it is for them to do in the business realm when they’re talking about a product rather than people. So it’s the same problem, different application of it, I think.

Cory: Right! And what about the pressure? I think of how magical that sounds, the “we’re we’re thinking about that third generation.” We’ve got 27 people, and they’re all happy and thriving. And oftentimes, that story is told, and sometimes people are sold the idea that this is what it means to thrive as a family. I think that there can also be the pressures as it relates to that, that we need to get to this definition of success. So as people are thinking about, and families are really building that governance, how do you think of it as it’s not a failure if individuals are thriving, but they’re not maybe thriving together?

Kristen: I do think about that a lot. There’s certainly a lot of pressure for rising generation family members to succeed. Sometimes that manifests often. That manifests in academic success early on. You know, mom and dad went to these schools. Everyone in our family has gone to these certain schools, and so I need to do that. Or regardless of the school that you’re attending, I need to be in the top 10% of that. These families often have a culture of uber success in whatever they’re putting their hand to. And so never mind that pressure, but it can often be the pressure of thriving in your career role. And, you know, everyone’s expected to go make a contribution.

But then also thriving as a parent, once people are having kids and raising their own next generation that you need to raise them so that they’re not entitled, and then thriving in your stewardship role. And so you need to come to these family meetings and make time for all of this, and educate and prepare yourself as a future beneficiary of these resources. And then it begins to be more things on your plate than you actually have room for. And so in addition to that, we’re also wearing the hat of we have these family relationships, and we also have these business relationships, and all of that needs to be humming along beautifully. And there’s really then no space for someone to have a struggle. It feels like it’s high stakes to have a struggle because what happens if I don’t go to the family meeting? What happens when the many roles and responsibilities that I have begin to clash? And it means that being at the family meeting means that I can’t be at parent-teacher conference, and I have to take time off of work, and there’s an important meeting, that this all starts to feel challenging to figure out which priority is the most important priority. And no matter what I’m doing, I’m disappointing someone in one of these roles. That can feel like a lot of pressure. How can you be winning at all of those things all of the time?

Cory: Absolutely. And so when we talk about that culture in families, how do we redefine some of that? When you think about thriving and what that has looked like in the past versus what it might look like in the future. Like, everyone going to those those certain schools, being in that certain quartile or decile of what they’re doing scholastically or career, those choices, how do we define that for what it means to us so that maybe we can be free of some of those pressures, but still feel proud and and have that culture?

Kristen: Well, in coaching, what we often discover is that some of that is pressure that we’ve put on ourselves. I’ll often ask the question, who told you that? So people will make an assumption. Well, I, you know, I have to do x, y, and z. Who told you that you have to do x, y, and z? And sometimes that reveals that, well, no one told me that. I just sort of read the tea leaves, and I feel like everyone else has done that in my family, and so I have to do it too. So it’s pressure that we’re putting on ourselves that maybe no one ever intended to put on us, and that’s actually not an expectation.

Then sometimes they’re unwritten rules that the family does actually have an expectation around that we’ve never written down overtly, but it sure would be helpful if we would because it is, and we encourage our rising gens, if they don’t have these unwritten rules written within their families, to try to inspire this as a means of of change and innovation, to codify some of the minimum expectations of what it means to be a good enough steward in their families. And I started calling this the MVP Standards.

I don’t know much at all about the area of technology and websites, but I do know that I learned along the way that when you’re building a new website, they will say, like, just give it to MVP, which doesn’t mean most valuable player, but minimally viable standard. And so we’ve got this minimally viable product. We’re going to put it up, and then we’ll work out the kinks. But at least everyone knows it’s what the good enough standard is.

And so I was in this meeting, and with my mind wandering, because I wasn’t most interested in what we were talking about, thinking that what rising generation family members really need is the opportunity. Like, somebody just tell me what the minimum standards are so that when I’m up against parent-teacher conference, missing an important meeting at work, or missing this family responsibility, I can know if I’m in compliance or not. Because often, they’re desperate to know what the expectations of them are. Almost like the rubric, if I can apply it to school. Like, what do I need to do to get an “a” here? What would I have to do to get kicked out of even being a beneficiary in this family? And then so that I can, in my own life, be making decisions about all of the different priorities in a way that’s informed.

And so this is something that we like to encourage families to do. Literally write down what are the roles that are in your family. One of them certainly is being a stakeholder, and that applies even if you’re a spouse, because you have stakes in the game of this family, and there are benefits that you receive, and there are expectations. Certainly in complex family enterprises, there are certainly expectations for married-ins.

And then if you’re a shareholder or a future shareholder, you know, future beneficiary, what are some of the minimum expectations that are expected of you? These are often unwritten. And so only when someone kind of breaks the rules is there then an intervention, but people are pretty desperate to understand what are some of the expectations that we have. And if there are two family meetings a year and they’re in-person, are you expected to come to both of them? Does your spouse need to come too? Can a spouse stay home to watch the kids? It seems silly to get into that level of detail on one hand, but people are really desperate for it so that they can know and be clear with each other, not unlike a job description. I mean, much of what we’re doing in a family enterprise is some aspect of a business role. And if we can create more of a job description about what it means to be a good enough beneficiary, that would be really helpful to people. And it would also be helpful to know, what do I do if I want to be really kind of a rock star beneficiary and I’m interested in being a leader in my family enterprise? What types of things can I be doing then to show that I’m interested in sort of moving up in this family organization?

Cory: I love that, because some of these roles, they’re not defined, and some people don’t even know that they hold that role. And so, as you mentioned that culture in the family as it relates to exterior roles or perceptions of society, there’s also those perceptions of the family and the perception of oneself. And so you made mention of some of those roles. Where do people start to understand this? If you think of the families that have come to you and they’ve said, you know, we feel like we have the success, but we’ve got all this pressure. Where do they start to really define those roles and get those MVPs?

Kristen: I think part of where the insight for this is happening, and it sort of speaks to what we were talking about earlier. So we educate rising generation family members as well as the leading gen, but focused on the rising gen now in peer groups. And it’s interesting to see how that’s another means by which we can begin to see outside of our own current reality. And so it’s helpful for them to hear the experience of one another so that they can go, “that’s interesting.” It reminds me of when you were, like, eight years old and you went to sleep over at a friend’s house, and you were like, “that’s interesting.” They have a whole different approach to eating dinner together, or bedtime, or whatever. I think that that’s what it offers. You know, this is an isolating experience being from a successful family.

And so when they have the opportunity to hear each other’s stories, they go, “that’s interesting. That’s not how we do it, but I can see value there.” And if nothing else, it gives them the opportunity to see their own opportunities for development, their own strengths. And that seems to be a point at which they start to go, what we do is not what everyone does. There’s some magic to what we do, and there’s some opportunity for development in what we’re doing. And I think that can help propel them to begin to codify in whatever way you can their approach to doing things.

And there’s a structured way that we in our rising gen cohort curriculum, that we teach people to kind of think about concentric circles of different roles. So everyone is a stakeholder, and then some of those stakeholders are shareholders. Maybe it’s not the married-ins, or bloodline. For a lot of families, that’s how they draw the difference between a stakeholder and a shareholder. And I bet there’s different expectations for how much financial knowledge you need to have between being a stakeholder and a shareholder. But I bet you there’s a similar expectation around privacy with regard to the family wealth or family enterprise for both. And then if you go in another circle, some of those shareholders are also in leadership. They’re on a family council, or they’re in the family philanthropy in some way. And so then there’s this different set of expectations about what you need to know, and how you need to interact and show up there. And then you get into an ownership circle, like an active ownership circle, and there’s probably the longest list of expectations.

But to be able to define all of that, and then importantly, also describe or define a path to being in any one of those circles. There’s often a lot of confusion around “what if I’m interested in being on our foundation board?” Is there a path to getting that job or is it like, I’ll just get tapped? That leads to a lot of confusion as well. So the more all of that can be defined, the more helpful it is. And I think probably people worry about doing that because they feel like they’re writing it in concrete, and we don’t know what will happen. And that’s okay. I think agility is one of the most important aspects the family enterprise can have. And so you expect that that will change, but it often brings a lot of comfort to people just even to have the conversation. And often you realize when you’re having the conversation with those families that I’ve been able to witness having it, there’s not always clarity. Like when you have the discussion, you realize we’re not necessarily all on the same page about this. No wonder we’ve been confused and sort of stepping on one another’s toes. So that’s an important conversation to have.

Cory: Right! So Kristen, as you talk about path, it makes me question, as well, autonomy of that path. So as a family, we might lay it out and say, if you want to be in this role, here’s what this looks like. But sometimes the family council has said, well, this is our expectation. We think that this rising gen member is going to take this path to this role. And maybe that member doesn’t even know that the family’s thinking that. And so when it comes to autonomy and that freedom of choice, how do we think longer term and think development while also being flexible enough to allow that person to say, this isn’t for me?

Kristen: Because that’s important from the standpoint of understanding the emotion behind being a beneficiary. Often, a beneficiary who thinks, I don’t know if I have the capacity for that role, or I don’t know if I have the interest in that role. To say no can feel like disloyalty and ingratitude, and no inheritor wants to feel that way. And at the same time, to do something and to engage in a role that you don’t feel equipped or interested in out of obligation also does not feel good either.

So I think for families to begin having these conversations much earlier than they often do, I remember I remember one client, but it’s not one client that I’ve had this conversation with. It’s been many of our rising gen clients who have this as kind of a theme in their lives where mom and dad kind of even though the rising gen knows that there’s wealth there, it sort of, how does it apply to me? I don’t know. So mom and dad really weren’t talking about it, and they encourage their kids to get the best degree you can and the best industry you can. And then they do that, and then it’s around, like, I don’t know, 27 because there’ll be distribution starting at 30, for example. But they sit them down and say, by the way, you’re going to have a ridiculous amount of wealth in this trust that you have access to and many of these stewardship responsibilities. And this person is going, I became an estate planning attorney, or a doctor, or an engineer, and I don’t really have time for that in my life. Like, I chose a life where my career takes up a big chunk of my plate of time and energy. And you’re telling me that I basically am going to have a part time job now, and need to meet with advisors quarterly. And that would have been helpful to know because I might not have gone down the same career path that I chose if I had known that I have this other responsibility. It’s a very significant responsibility in my life. And so that can feel very disorienting to people.

And while I understand the leading generation’s concerns about not wanting to derail the life interest, passion, profession of the rising generation, I think we are doing them a disservice in withholding that information from them. And this applies most to the families where the stewardship role is a really time intensive role, or requires a lot of preparation or what have you. But at the same time, for them to understand, and I’ve had clients who’ve said, I’m literally going to leave my career now and go do the thing that I always would have wanted to do that still making a contribution in some important way to the world, but is much more aligned with my areas of passion. So in that regard, we’re not doing right by our rising generation family members if they are really struggling to plan their life course now as a second phase, now that they have all the information.

Cory: Right! And so, shifting gears slightly to that leading gen, we’ve talked about a lot of the interaction between the leading gen and the rising gen, and what they can do to help prepare the rising gen. But what about the leading gen in their next phase? Some of that territory where our rising gen is now, the now gen. They’ve really taken a lot of the lead. They’ve developed into those roles. And now we’re a little bit more mature, now we’re thinking of our roles differently. Where does some of that that peer group work that you do, or or does some of the peer group work that you do, really touch on that of now we’re we’re transitioning to this other part of our life, and and some of the work that’s equally as important, but we’ve now developed that next generation and they’re taking a lot of the the leading control?

Kristen: I think that’s tricky. And I think we have a long way to go in the industry in preparing people to be, what I’ve started thinking about is middle gen, and I’ve heard some other people in the industry call sandwich gen, which I think is interesting, because in the culture at large, there’s a lot of conversation about the challenge of being sandwiched between caring for older adult parents, and caring for kids who might still be in the home. And how can we apply that to the field of people who, in addition to career and personal responsibilities, also have family stewardship responsibilities as well? So your question is an important one.

And for the middle generation, they often, especially when it’s transition from the previous leading generation having a style of leadership that was different than how their style of leadership will be. And an example of that is, we have a lot of rising gen clients whose mother or father is doing self directed investments. And so as leadership moves to them, they really need to have a whole revamp of their family enterprise, because now this is not centered around making direct investments anymore. It’s going to be centered around more of connecting to someone who’s running managed investments for you. And it’s really a whole different style of running your family enterprise. And now you have a management role over advisers, but we don’t necessarily prepare that generation to be able to run that leg of the race uniquely.

And so often, how we prepare them is for the gen to fill in the shoes of the generation that is currently leading, we prepare them for those responsibilities. And, really, what we need to be doing is, as much as possible, looking into the future and preparing them for the leg of the race that they will uniquely run. And it could be that the family enterprise is changing as I just described, but it might also be that that generation or that individual has a really unique approach to leadership based on their own passions and strengths. I’ll use the example of, maybe the incoming generation is really passionate about impact investing and being really mindful of how their investments can do good in the world, in addition to making good returns. That’s a completely different approach to investing and completely upends your investment policy approach, and probably what advisors you’re working with. And so preparing the next generation to lead for their unique leg of the brace, I think, is an often missed approach.

Cory: Right! And thinking of some of that in the sandwich generation as you mentioned, it may or may not be called. But thinking about it as that generation gets older and their needs change. So now we’re talking about caring for the elder generation. How can we, as a family enterprise, be thinking about that in some of the emotional burden, but as well as some of the time that it requires families to pay attention, and still paying respect and honor to those people as where they’ve they’ve come from, how they’ve helped us get to where we are, and ensuring that they’re cared for and honored?

Kristen: I love your question, and I think it’s another one of the big mountains that we need to climb as practitioners to help families navigate through this, because this is some of the toughest stuff. I have walked my own mother through a diagnosis of Alzheimer’s and passing of Alzheimer’s, and that is some of the hardest stuff that you will ever face in life. I look ahead to my own future, and I’ve done what I can to incorporate into my own planning. I’m doing what I can to avoid an Alzheimer’s diagnosis. And I know that there’s a risk for all of us, that we could end up in this position. And so both from a technical planning standpoint, but also from the standpoint of the more emotional side, as you mentioned, it’s really important for us to be having conversations about this as a family before, and hopefully, we never get into that position, but before we’re in that position.

So if we can normalize more of those conversations as a standard, I don’t know. Did we start talking about this at 50 and that’s just on the agenda before we can get out in front of it? Because of the experience that I have had both with my father passing early, and my husband’s parents also passed rather young, and then walking my mom through the situation that she was in with Alzheimer’s. For us, it’s given us permission to be able to have these conversations as a family more proactively. But I think it’s important for everyone so that you’re not navigating through the emotions and the planning in the midst of the whirlwind of the situation. So all of that’s important.

And another point that’s really interesting with regard to all of that, often when a situation happens where a family member needs caregiving, physical caregiving, or they’re dealing with a dementia diagnosis, you often see the family member who’s been sitting on the sidelines at the investment focused meetings becomes the leader of coordination of care, and taking on some of those more human roles.

And there was one family in particular that I watched really honor the person who in their family, the rising gen family member, who sort of hadn’t stepped into a role in the past. And all of a sudden, she becomes the rock star, the shining star of the family when a situation like that happens where it’s more of a human need to care for. And so it’s really easy to say, okay, who’s going to run the family philanthropy? Who’s going to run the investment, the approach to our investments? But it’s important to plan for who’s going to be the person who’s going to coordinate the care of older adults, and who’s going to coordinate the life crisis that inevitably, sadly, families find themselves in from time to time. That’s often your family champion type person, and that’s often the person that has felt historically like they didn’t have a place in the family enterprise.

Cory: Right! And so much,  I don’t know if this is a North American thing, but really within our culture and our society, it’s uncharted territories often. there’s not a lot of storytelling or examples of how families have done this and done it well. And so I think, as you mentioned, as advisors, and as we go forward, that really needs to to be considered. We do risk-planning for business. What about that risk-planning for family? Is it 50, or when is it that we start bringing that conversation into those family council meetings and family meetings? But it’s so important that we do.

Kristen: It’s interesting that you brought up culture. I don’t know if it’s North American culture or if it’s just humanity that makes us think that there’s certain things that we want to save other people from knowing about in our own personal experience. But I think that there might be something there to consider.

For example, when I was going through, especially the end stages with my mom, I would hop on a work call. And when someone said, how are things going? Instead of being like, good, thanks for asking, I would say, it’s pretty bad over here. And, we’re doing everything we can to keep it together, and here’s how we’re handling it. And what I noticed that did, that authenticity in helping people to have a glimpse of what we were dealing with did, is that, you know, for example, when my my work friends that understood what I was going through, when two years later they were dealing with the same thing with their parent, would share with me, I’ve really taken strength in getting through this knowing that you two went through it. So it’s less about me even telling them how I did it. It’s really just solidarity of knowing I’m not the only one who’s going through this. Kristen got through it. I can get through it. And so if we don’t share with each other just bits and pieces of that, and we feel like we need to shove it down or hide it because gee, no one wants to hear about that, or that’s too scary and upsetting, we’re really doing a disservice to one another, because they do think there’s some solidarity. And of course we need people to say like, how did you navigate finding a caregiver, you know, professional caregiver or whatever?

Cory: Absolutely! Kristen, as we near the end of our conversation, and I very much appreciated our conversation. And unfortunately, we do need to wrap it up. There’s a few questions that I ask each guest. Are you ready for the tough ones?

Kristen: Let’s do it!

Cory: Alright! What is one key strategy that you believe is most essential for building a successful family enterprise?

Kristen: I think having a beginner’s mind is surprisingly essential. One of the ways that we feel confident in our approach, especially in the arena of business, is by moving ahead with authority and boldness. And I think there’s a way in family enterprise that we can move forward with boldness and confidence while keeping a beginner’s mind, knowing that there is a lot to learn and be aware of, because things in a family and in a family enterprise, they’re constantly changing. So as soon as you think you’ve got it nailed, all of a sudden you realize your next generation is a decade older than they were in what seemed like five minutes ago. And so to keep adapting, sort of like the business or industry side of things, and to always be ready to adapt to your changing family. Now you’ve got in-laws who are coming in. How are you going to adapt to that? To not not assume, well, we’ve been doing it this way for so long. Like, we know exactly how to do this. To have a beginner’s mind with each stage of that so that you can get ahead of the innovative thinking that you need to succeed in the next iteration of your family’s story.

Cory: Fantastic! And what is the most common challenge that you see family enterprises encountering when it comes to wealth transition and generational continuity?

Kristen: I think it’s functioning today as if the dynamics of your family enterprise are going to remain as they are today. Really, you need to be doing your planning today for tomorrow’s world, and that tomorrow might be five years from now.

One of the strategies that I use to help people have this is really about vision, to help them have this vision is, I will say, imagine that I could give you a pair of magical binoculars. If you looked in them, you could see what your life and family looks like in ten, fifteen, or twenty years. And then like, look at what your family members are doing. Like, see your kids in their parenting role. See as they’re raising the next generation, see your kids juggling profession alongside stewardship responsibilities. What is your role? How are you showing up as a grandparent? And then take those binoculars off and say, okay, what are your hopes and dreams for their thriving and well-being in that moment?

And then what are some stepping stones that you can put in your family’s path to get you closer to the vision that you hope for? Because it is really hard to see outside of the moment that you’re in. And the more you can help yourself see the vision of the future that you’re hoping for and try to just, you know, no guarantees. We don’t know what the future will actually hold. I can’t give you those magic binoculars. But to be able to set some stepping stones in the path to make you more likely to get there is just what we try to do.

Cory: I love that! And, yeah, that visioning, how much more prepared you can be if you just even have had that awareness at some point. And those binoculars, I’m sure, do wonders for people. So that’s fantastic.

Now in your experience, what are the top three key qualities that successful family enterprise leaders possess?

Kristen: I think an openness to the idea that how they’ve been doing it and have found success in doing it might not be the only way to be successful. So I think when a founder can see and acknowledge I’ve had, and they always have, I mean, this is truth. I’ve had some incredible success in life, and what I’ve been able to do is extraordinary. And when they can recognize that menu of how I did that, or that plan that I had to accomplish that, is not necessarily the plan for what it’s going to take to be successful at growing this, or rocking this life in the next iteration of it. So I think that that really requires a humility, and an openness, and an agility to know, okay, we can shift the plan and still find success. Being able to hear the next generation and be open to them in that, I think, is a really important approach to take and maybe one of the most important approaches to take.

I also think that because this is, like, you know, family and business, it’s layered, that forgiveness and empathy are really important. We spend a lot of time in our rising gen peer groups talking about the importance of knowing that our parents did not get a manual of how to do this, and they are still trying to figure it out. They’ve never done this before either. So to be able to have empathy for the situation of our family members, whether it’s your sibling, or whether it’s a parent or whether it’s your child, to have a lot of empathy to know we don’t know, we all don’t know what we’re doing. We’re just trying to get through this in the best way that we can, and thrive alongside of each other. And then when we don’t get it right, to be able to turn around and have forgiveness for them and really try to make repair, and know that we’re not always right, and everyone has their own experience of life.

And then it’s hard to not after the conversation we’ve had to really highlight vision and being a key component and strength.

Cory: Fantastic! So many good things there. And I think of your three qualities, we could have a whole another podcast on that. So we’ll leave it there because I could ask you lots of questions. But as we conclude our conversation, I’d like to highlight where our listeners can engage in more of the conversations that you’re having, as well as maybe some of the conversations that others are having as it relates to the conversations we had. Could you kindly provide our guests where they could find you and some of those resources?

Kristen: Yes, they can definitely find me at www.in3generations.com. You can use the number three or the word three. We are also on Instagram. So I’m working hard to try to get some of the information and resources that we deliver in our peer groups to the general public. And so we roll a lot of that on Instagram and on LinkedIn. So we hope that you will look for our page there.

As we were talking, I found myself thinking about the book, The Quest for Legitimacy by Jamie Weiner. I think a lot of the rising gen topics that we were discussing reminded me of that. So I think that that’s kind of a good launching place for anyone who’s sort of intrigued by the topics we were talking about, and ready to learn more.

Cory: Fantastic! And I wanted to make sure that we covered everything today. Is there anything else that you’d like to share with our audience that maybe we didn’t get a chance to touch on?

Kristen: It’s a good question. I think I’m an advocate for family members resourcing themselves and beginning to think, I think there’s a risk in this stewardship role. I think it happens to leading gen too, where all of this can feel complex and overwhelming. And because of that, it can be really easy to sort of put it in the “to think about” bucket and then never get there. And what I’m really trying to do is to help the world integrate all of this and not compartmentalize it, and make it something that can feel really achievable. So I think that there’s a way to kind of hack all of what feels very complex into kind of small digestible bites of learning and development. And so I guess if I have a message for people, it’s just all of this doesn’t have to feel so daunting. I think there’s a way to make small incremental steps that make an enormous difference in the lives of your family members and in your own growth and well-being.

Cory: Amazing! And what a great message to leave us on, Kristen. Thank you so much for taking the time to share your expertise, experiences, and all those great stories with us today. Your insights have been incredibly valuable to me. So thank you so much for providing your contribution to our episode. And I know that our listeners will be grateful for everything you’ve shared.

Kristen: Thanks for the opportunity to be here, Cory.

As we wrap up this episode, we invite you to reflect on Kristen’s approach to listening to your life, breaking free from autopilot, and creating intentional spaces for growth and self-discovery.

Whether you are part of a family enterprise or provide consulting to family businesses, Kristen’s insights remind us that true development isn’t about meeting external expectations, but rather about having the courage to define our standards and create authentic conversations about choosing our own story.

Throughout our discussion, we explored how families can break free from unwritten rules and self-imposed pressures that keep them stuck in patterns of expectation. Kristen emphasised how genuine development requires moving beyond the assumption that everyone must follow the same path to success. We also discussed practical approaches to family dynamics, from creating MVP standards that define “good enough” participation to fostering early conversations about wealth responsibility. These perspectives provide families with thoughtful frameworks to navigate role clarity, honour individual autonomy while maintaining connection, and build governance structures that balance collective purpose with personal freedom.

For those seeking expert guidance on family development, Kristen Heaney from In Three Generations, LLC is ready to support your journey. You might also want to pick up copies of her books, “In Three Generations: A Story about Family, Wealth, and Beating the Odds” and “The Super Special, Altogether Ordinary Day,” both available on Amazon. We’ve also included additional resources and contact information of Kristen in the show notes.

Disclaimer:

This program was prepared by Cory Gagnon who is a Senior Wealth Advisor with Beacon Family Office at Assante Financial Management Ltd. This is not an official program of Assante Financial Management, and the statements and opinions expressed during this podcast are not necessarily those of Assante Financial Management. This show is intended for general information only and may not apply to all listeners or investors; please obtain professional financial advice or contact us at BeaconFamilyOffice@Assante.com or visit BeaconFamilyOffice.com to discuss your particular circumstances before acting on the information presented.