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Our Family Office is proud to announce the launch of the Our Family Office Podcast. Throughout the course of the inaugural season, host Adam Fisch speaks to various guests from across our firm, offering insights into the areas of focus for an integrated family office, and the ways that a Shared Family Office™ can help Canada’s wealthiest families.
Welcome back to the Our Family Office podcast. I'm your host, Adam Fisch. This season, we're talking about the rising generation and what makes them unique. On this episode, you'll hear a conversation I had with Jess McGawley, a qualified psychological consultant and mediator who works with ultra high net worth families focusing on the rising generation. Jess is the founder of Dallington Associates, a London based firm that provides discreet, highly tailored mentoring and psychological consulting for young inheritors, helping them step into adulthood with confidence, clarity, and a deeper understanding of their role within the family system and the wider world.
Adam Fisch:As you'll hear, Jess's work is really different. She focuses on young people as they're figuring out their identities and she helps wealthy parents navigate those challenges alongside them. It's true hands on work with a group that's often misunderstood and I think it's so important. In this conversation, you'll hear us discuss the unique challenges that wealthy adolescents face, the importance of failing well, and some success stories from her work at Dallington. I hope you enjoy it.
Adam Fisch:Jess, thanks so much for being here.
Jess McGawley:Thank you for having me.
Adam Fisch:So to start with, can you talk a little bit to our listeners about your background and how you came to build Dallington to meet a specific need among high net worth families.
Jess McGawley:Absolutely. So my my background is sort of twofold as to why I got into this. On the one hand, I come from a family business where that fell victim to the now disproven saying of in three generations. So I grew up a lot around hearing those stories about what went wrong, and they weren't they weren't technical matters. They were relationship community matters.
Jess McGawley:And so I've always grown up knowing that they are so important. But the other side is that I worked in a family office advisory for about seven years whilst I was at the Tavistock Mental Health Hospital in London doing some training in consulting psychology. And I just kept on seeing this gap for young people in the family office advisory and I said, look guys, I really think we are missing a younger cohort, 16 plus, you know. They're at school or the ones going to college and university and they need a slightly, you know, they need a bit of a curriculum and a bit of support just for them because the average client we have is a beneficiary of a trust but none of them know what that means, what that word means, and none of them are prepared for it, and that seems like a real disservice. So ten years later and a 150 families later, it's proven to be- to work.
Adam Fisch:Yeah. And it is as you said, it's meeting such a specific need because the challenges that are faced in these families and for these inheritors, other people really wouldn't necessarily understand or be able to relate to.
Jess McGawley:No. Not at all. And it's about having that space that's very empathetic, but also increasingly, I think is important, straight talking. You know, there is a lot of really wonderful research and theory around these families, but what is often missing, I find, is just that very direct, look, if you're a 16 year old, things probably feel a bit topsy-turvy anyway. This is some straightforward advice and equally to parents.
Adam Fisch:So when you are working with those young inheritors, how much of the work is around, like you said, just the normal topsy-turvy stuff versus those unique challenges that are specific to ultra high net worth families?
Jess McGawley:Such a good question, Adam. I think it's so important. I would say 75% of it is normal adolescent stuff. And nearly every single mentee that comes through our door, young person, they say this line, which is, I just wanna be a normal kid. Just wanna be a normal teenager, a normal 20 something, but I know I'm not.
Jess McGawley:Now they are all the sorts of things that they're bringing into sessions are their friendships, their relationships, the fact that they're struggling in a class, they're on the wrong university programme, etcetera, those sorts of things. And they're issues that a lot of young people go through. But then there's that added lens, of course, of the wealth, and and I'm sure we'll we'll talk about this later, but the difference of coming from a wealthy family and a family business wealthy family. Yeah.
Adam Fisch:So let's talk about the unique challenges. So the things that aren't just regular teenage stuff. What are some of those unique challenges that you've found are the most common among this demographic?
Jess McGawley:Okay. So I think the biggest let's start with the biggest misconception, which is that coming from a wealthy family, a prominent, you know, family business family makes adolescence easier. Now, of course, of course, wealth brings privilege. We're not denying that. I think that would be, you know, very risky to do that.
Jess McGawley:At the same time, for anyone listening to this, I think we all remember our adolescent years are all about identity formation. It's all about, you know, in the different hats that you wear during that time. I myself had multiple personalities and identities during the ages of, you know, 15 to 20, I'm sure. But if you are growing up and people are telling you who you are, be that: family, friends, society, the media, and they're saying because you come from this background, you have this net worth, we have decided who you are. That is really tough. And then we see a lot of young people really pushing against that. So I think that's one of the main misconceptions that we we should all have a little bit more empathy for, frankly.
Adam Fisch:Yeah. And so it sounds like what you're describing is this idea of, in this period of time where young people are forming their own identities, they're having an unusual amount of expectations placed upon them of who they should be. And working through those two things, like, it makes it even harder to find your own identity when the world is also telling you a specific thing that you should be.
Jess McGawley:Exactly. And then, you know, I think we have to remember that the average parent who is observing this didn't grow up with, you know, social media in the same way, and so it's just so much more magnified and reinforced. And, you know, that message will be reinforced by maybe their friendship group, but also just externally. I've had so many young people get to college and their first week, they're freshmen or freshers as we call it in The UK, and they've had people who have, you know, googled them, looked them up on social media, they know who they are, they know who their family is, and they have not been given a beat to just find their way and to find their people and, you know, that that's really tough.
Adam Fisch:Yeah. Well, like you said, to to your point about between fifteen and twenty, you tried on a bunch of different identities. Well How much opportunity do you have to do that when people have already looked up who you are and made assumptions about who you are, who your family is, all that. Right?
Jess McGawley:Exactly. Exactly. And you know, a lot of the families, certainly for family businesses that I work with, the parents' generation or the grandparents maybe who who started the the business, maybe the business is in something that isn't as favorable today for a younger generation, you know, an industry that, now has a more critical lens on it, and maybe the right reason, that is not the inheritor's fault. That's not their they didn't decide it. They didn't, you know, design that industry, but yet they really pay the price by their peers judging them for it.
Adam Fisch:Yeah. I wanna talk a bit about the parenting angle of it. So you've spoken before about how parents in an effort to help their children sometimes remove opportunities to overcome challenges and build resilience.
Jess McGawley:Mhmm.
Adam Fisch:In your experience, what are some of the downsides of making things too easy for the next generation?
Jess McGawley:So I would flip that on its head and say, are the upsides?
Adam Fisch:Mhmm.
Jess McGawley:Because I'd say some of the not just resilient, but the most content, happy young adults, you know, normal levels of up and down that I've seen, are the ones where they have had to work things out for themselves, and they've had to pick themselves up. Now the reason why specifically G1, certainly, first generation wealth creators are so resilient is because they are such excellent problem solvers. They would have had to have solved a million problems every day through that whole transition period of building what they've built. And inadvertently, with love, with best intention, they sometimes remove that, because they now have these resources and the ability, frankly, to fix a problem. If their child comes to them and says I have a problem, they've got an answer. I guarantee it.
Jess McGawley:Does it mean that they should act on that answer? Not always. I would actually say unless it's an emergency, we should all try and hold back a little bit. And, again, this is just based on my experience, is the average young person is far, far more capable than we think they are and give them credit for. At the same time, they themselves will think they can do far more than they can, and it's about meeting somewhere in the middle.
Adam Fisch:Right. And I guess that's it's natural really at any level of wealth, but as you said, right, at very high levels of wealth, there's just more resources to step in and solve whatever the problem is.
Jess McGawley:And it's not just them. I always say, you know, if raising for anyone who's listening who has a child or is in any way a caregiver, you know, it's a group effort. Right? It's hopefully, raising children together, but less so that now that maybe there wasn't a as you know, in the past or in our in our grandparents' generation perhaps. But the rising generation's village today is all of us, you know?
Jess McGawley:It's advisers, it's tutors, it's coaches, it's, you know, their school, other parents, your peers. So we somewhat have to collectively decide that we're going to allow this younger generation to stumble a bit more. It's about saying, well, you know, if I fix every problem for my child, but Jane over the road doesn't, what does that mean? We all sort of have to agree together that we're just gonna try a little bit harder to step back and allow our children to step up.
Adam Fisch:And it could be hard as a parent, obviously. Like, we're parents and you know, to to watch your kids stumble and have you know, there is that instinct. Right? It's a biological instinct to come in and help your child and caregiver, but it's almost fighting against that evolutionary push to say, like, no. This is actually longer term for their benefit to figure this out.
Jess McGawley:Adam, that's 100% it. I always just think you are thinking about future, you know, name of child. So I always my son's name is Flynn, my eldest, and I always think I'm doing this for future Flynn. This is not right now. And I should also add that everything I say on this call with you and on this podcast in general, I promise you I have got wrong myself, and that I'm not perfect at and I've tested.
Jess McGawley:But my husband and I sat down a couple of years ago, and, you know, both of us are also, you know, busy working, have our own businesses, really enjoy that, want to be there. And does it come the weekend or a holiday? And do we maybe step in a bit too much and gift a bit too much? Absolutely. And I was like, we need to collectively do this together, and let's just see what happens. And it was amazing. He just steps up more. Absolutely. And then when I step in, he knows I mean it. There's a reason for it.
Adam Fisch:One thing that I think about in this way is, is it your job to raise a happy child, or is it your job to raise someone who will be a well adjusted adult? Because what makes you happy as a child is not always going to be the things that set you up for success longer term.
Jess McGawley:I completely agree. And I think it's a really difficult one to find the balance, but it is important to try and find the balance. What I hear a lot from parents, especially again if they're first generation wealth parents, is that really, if we're talking quite frankly here, there is an element of trauma sometimes in their childhood, and they've had a really tough time. And they they want to find the balance between, well, I don't want to put my child in such stressful situations as I grew up in. At the same time, I'm over gifting. I'm overcompensating. I'm over fixing. Where's the middle ground? And so I think it is you're absolutely right. You're thinking about that future child, and the word I always come back to is capable. We just want to make capable young people, and you can do that whilst also having a good time.
Adam Fisch:Right. And one of the things that I think can interfere from the child's perspective in their own development in that way that I think you often see in very wealthy families is a fear of failure. Right? Whether it's just because their child their parents have stepped in a lot or because they see their parents as these massive successes, and how do I keep up? What have you seen in your experience of that fear of failure in the next gen and kind of how have you helped them work through that?
Jess McGawley:Okay. So I think it's, two things that I've seen repeatedly. They tend to go hand in hand. One is a genuine let's say, they haven't practiced failing.
Jess McGawley:You know? You can get really good at failing. And I'm sure all of the parents who are the, you know, the wealth creators or who run successful businesses know that know what I mean by that. You can get really good at going, right, this one I learned from. I'm not gonna dwell on it too much.
Jess McGawley:I'm still a decent human being. Let's carry on. So there's practicing failure. That's one thing. But then there is this added pressure, which the parents' generation might not have had so much if they're G1, which is fear of living up to expectations.
Adam Fisch:Right.
Jess McGawley:Now people often misconstrue that as thinking that's parents' expectations, but it's actually a lot of the time it's also their own, that young person's expectations of themselves, it's society's, it's even their teachers. You know, they're going, look at who your parents are. You know? They're exceptional human beings, therefore you must be. Now, I think the thing where we do go wrong is that we tell young people that they can be anything.
Jess McGawley:You can do anything. If you can think it, you can dream it, you can do it. Now it's a tough one because in some ways that is true of their parents, if they're super successful. You know, they have done that. That doesn't always mean it's going to be the case for their child, and it's a hell of a lot of pressure to put on somebody.
Jess McGawley:So I think it's important to encourage young people to dream big and to have big ideas. Absolutely. But don't push them against what's actually realistic, to some degree. And if they have something that they feel really passionately about, you know, empower them on that journey. Encourage them.
Adam Fisch:Yeah. And I think what you said there is so insightful. And the idea of, you know, you could do anything and the pressure that that can put on
Jess McGawley:Mhmm.
Adam Fisch:I think it's so important to couple that with the trying and failing and getting good at failing because it's this idea of, yes, you have lots of opportunity. We're not expecting you to get it perfect the first time. Like, you can do anything doesn't mean you have to go and immediately find the perfect thing, and you're perfect at it, and everything's amazing.
Jess McGawley:Exactly.
Adam Fisch:No. What it means is you have the opportunity to try and fail and do different things and move on to the next. And the most important part is the moving on to the next. Right? And not stopping and dwelling.
Jess McGawley:Exactly. And just, whilst moving on to the next experience, I'd also say just the discipline of sticking at something as well. Like, if whilst moving on to the next, I hear the narrative you're talking about. But something I also see is parents going, well, you tried that. You didn't like it. Don't worry. There are resources. You can try a new business. You can go to a different college. That really should not be the fallback.
Adam Fisch:Yep. No. I think that that's a great point. And, again, as you were alluding to a few minutes ago, it's about balance. Yeah.
Adam Fisch:Right? Is that there should be there is room for try different things. If it doesn't work, you go to the next. And there's the idea of and also, we finish what we started.
Jess McGawley:Exactly.
Adam Fisch:Right? Absolutely. So important to to pass on.
Jess McGawley:Mhmm. Agreed.
Adam Fisch:So you were talking earlier about wealthy families, you know, with and without a family business. So when there is no family business and maybe the children are third generation, the second generation isn't working now, you know, maybe there's been a liquidity event. How does that second generation who is not working or early retired, how do they teach their children about hard work and finding their own sense of purpose?
Jess McGawley:It's a really tough one. And frankly, unless the second generation themselves have done that work, really thought through it, I think it's a bit risky. So I would always encourage that generation to think about it as well. Mhmm. And you know what?
Jess McGawley:Before I answer your question, I think the difficulty of it being, when we say just wealth, of course that's still amazing that they have created that, maybe there has been a liquidity event. But the benefit of a business, even if it's a very small one, kept there, almost as a container, is it something to kick against? It's something to say, I do or I don't want this. And when you're young, being able to say, oh, I, you know, I disagree with the way that this this being run, therefore, I'll do it my way. It can be really helpful.
Jess McGawley:It can be really inspiring. So even if that business is no longer alive as it were, it is up to those previous generations to keep the story of it alive, explain how that money was created because at some point, it would most likely have come from a business. So, I think that part's important. In terms of engaging them, I always think community is really important. Now people assume that I'm gonna jump straight to philanthropy.
Jess McGawley:Now, of course, philanthropy is wonderful, but I think it's more important to get young people just engaged with other people in anything they're interested in. Be that in sport. Be that in a level playing field. I'm a big, big believer that young people of affluent families should, if they're up for it, get engaged in some kind of team sport. The reason I say this is because you can do everything right. You can train really hard. You can eat well. You can sleep well, and you can turn up on the day, and it just doesn't go your way. And it's not just on you. It's on the whole team.
Jess McGawley:Equally, you know, you can do everything wrong and you turn up and you just have some luck and you still win the match. I think it's a really important lesson in life, so I really encourage that.
Adam Fisch:Yeah. I think that's such a unique piece of advice to address that type of issue. But it totally makes sense that as you frame it that way. You have said before, I think, that parents tend to be better at preparing the assets for the child than the child for the assets.
Jess McGawley:Mhmm.
Adam Fisch:How would you like to see parents do a better job of that?
Jess McGawley:Well, firstly, as I've learned over the years, you really you can't say things like that without backing it out to parents, you know? They really want, they want the stats. They want something. So I say to them, okay, I want you to go and look at your role models. Who are the families of wealth who business or no business anymore, even if they've had a liquidity event, who are the ones that still seem to be together, you know?
Jess McGawley:Are they the ones that still spend time together? Maybe they've done retreats or they're in therapeutic work, are more relationally intact, let's say, and they will always come back after doing that homework and show you the ones that they've genuinely found role model families that have done that sort of work. And then they will find you the opposite, families who are maybe even more successful financially but have numerous lawsuits against each other. There've been numerous mental health problems, within the family. So the minute you get them to do their own homework on that, I find that's not me telling them.
Jess McGawley:That's them doing their own research and finding the importance of family role models, not just individuals. Family role models I think is so, so important. So that's one thing. I then just say, you know, if you spend even a quarter of the time that you invest in tax legal financial advice, in just understanding how wealth affects the psyche, how it's going to affect your children, you will soar, you know? You will just be so much better prepared.
Jess McGawley:Because a lot of that technical advice that, as you will know, you know, better than I do, a lot of that technical advice is also about risk mitigation. It's about understanding, okay, these are the potential issues that you're most likely gonna come up against because you're a family of wealth. Well, the same applies in emotional health and in family dynamics. So being able to say, look, guys, over the coming years, these are the sorts of things that might come up for you and them being better equipped with the language to use and the resources to go to, they're just they'll feel more confident.
Adam Fisch:Mhmm. And thinking about how parents and children communicate, because I know that's a big part of what you do, How do they strike a balance between communicating about the wealth and not keeping it a secret versus setting them up to they know a trust is coming. They're just waiting out the clock, and they're disincentivized from working hard.
Jess McGawley:Yes. It's a really, really tough one. And over the years, I've found that, you have to be very mind so I'm mindful of giving this advice because culturally, it will massively differ from one culture to another. And that's, of course, each their own. But I think it's a too much secrecy creates anxiety.
Jess McGawley:And as we know, the majority of secrets aren't good. People don't typically hold secrets for a positive reason. So if you are holding a secret about your net worth or where the money has come from, is that because there is some shame around it because you are worried about what it's going to do? If so, you as the parent should really address that with yourself before you bring it into conversation with your child, for sure. At the same time, absolutely too much information is demotivating.
Jess McGawley:Unfortunately, however, we live in a world where we don't necessarily have the privilege of restricting that information because the average 16 year old will find out if they if they want to. So I think a progressive sort of small drip feed, age appropriate way is best. And I know, you know, Adam, we've talked about this separately, but sort of from the age of seven, you can start having these conversations around what's the difference between, you know, net worth, self worth, getting a, let's say, a give, spend, save box, just introducing these topics to them. But as they get older, you know, really thinking of instead of thinking about it as money, thinking about it as values and as a tool for good.
Adam Fisch:So I wanna talk a bit about Dallington before we wrap up. So can you describe a little bit about what this program is like for young people? Because is such an unusual offering. And then maybe give some examples of some success stories of of young people that have gone through the program.
Jess McGawley:Definitely. Thank you. So, I should add that everything about Dallington, the way it runs today, is due to the feedback that we've had from our mentees and their parents. So when you set up a business, I'm sure lots of parents who are listening to this as business owners know, you set up a business thinking you know what your client wants. But if you're smart about it, you will find out quite quickly if that's true or not, you should pivot.
Jess McGawley:So I had a really good idea of what I thought people wanted ten years ago. And over the first couple of years of running Dallington, changed things quite rapidly because actually, number one, parents need to be involved. Even if their child is 16, 18, 22, and they want their independence, it's really important to involve a parent in some of the discussions that you're having so they do not feel, siphoned out, that they are aware of what's going on for their teenager, their young adult. Equally, it's important to have group work to get young people together so that they have that sort of peer network because the average mentee that we work with has friends from all walks of life but to sit in a room every so often with other people from similar backgrounds, similar sort of networks, and be able to, without shame, say, you know what? It's really tough.
Jess McGawley:Every time I accomplish anything, people tell me, well, that's because of who your mum is or who your dad is. And I think it's really important that they have that space every now and again to share that. So some examples of Dallington. So our mentees are typically with us for about eighteen months and we see them once or twice a week, either online or in person. But we really encourage in person for those who are obviously in London.
Jess McGawley:And the reason for eighteen months is that we are very, very big believers at Dallington that aren't like technical support. So by that, I mean, you know, financial, tax, legal, who you might have for your whole life and beyond, into the next generation. Our role is to empower you to stand on your own two feet. We are not supposed to be there for a significant amount of time. So we always say to them about eighteen months and then you should graduate our process because we believe you can do this.
Jess McGawley:So I think that's important. The way that it works is both practical and personal. We have a very practical curriculum, and that includes everything from how to manage conflict and how to have a difficult conversation with your siblings and cousins around wealth and who's working in the business, but also things like your ecosystem, beneficiary education. I should add we are not interested nor do we ever give any financial or legal advice. What we're saying is, like it or not, you are a beneficiary of a trust.
Jess McGawley:Therefore, do you know what that means? Do you understand what a trust versus a multifamily office, a single family office, a wealth manager, etcetera, is? Because most teenagers don't, but they have access to them. So we think it's really empowering for them to understand that ecosystem. On the other side, like I said earlier, really majority of it is just normal adolescent stuff, that they're all going through, and they need to have a place to share that.
Jess McGawley:Some good examples, I can think of is I have, these are both past graduated mentees. So, one female mentee from a Southeast Asian family, very, very bright and sort of fit into that, dare I say it, the good girl. She did everything right. You know? She got all the best grades.
Jess McGawley:She went to all- the right degree at the right college, then the right masters. She did exactly what her parents said and when. And then she found herself back home in the family business really quite frustrated that she didn't feel like she'd ever had her freedom years. She didn't feel like she'd ever found her voice. But she was never going to be the young person to, you know, walk away from the family or have huge conflict, and we wouldn't expect her to or encourage her to.
Jess McGawley:But what we did want her to do is find that bit more independence and so we hosted some family sessions, some mediated sessions to get her to speak up about this. And what happened eventually was that she ended up becoming what I think is the right term, an intrapreneur. So when you have your own sort of entrepreneurial
Adam Fisch:Right.
Jess McGawley:Umbrella within the family business.
Adam Fisch:Within the yeah.
Jess McGawley:Exactly. And and in her own building, it was still in the same complex, but her own building with her own team, and, you know, she also found her place there. So I think that's that was really a special case. Another young man, a situation where we get this a lot, when a parent comes to us and they say, we just don't understand, you know, our son, our daughter, for example. They are they're being very entitled.
Jess McGawley:We don't understand why they're not grateful for everything we've done for them. So the first part of that is always to say to a parent, let's take accountability because, you know, typically young people don't entitle themselves, so they have got here because for whatever reason, we have paved the way and made things easy. So before we get upset with them, let's just understand why this has happened in a non judgmental way. But let's do that first. But it was that.
Jess McGawley:It was for them. There was a lot of guilt about not being around a lot. They'd moved, I think, you know, five, six times, different countries. And their way of managing that was to maybe over gift a little bit and to say yes a little bit too much and not have consequences for when things went wrong. And so suddenly they're looking at this, you know, near 20 year old young man going, you know, when I was your age, I was running a small business.
Jess McGawley:I don't understand how this has happened. So taking that accountability first. But we found the best thing for him other than family sessions was to volunteer, to offer volunteer mentorship at a academy school, near us in London where he would basically do tuition, math tuition, but he was very, very bright, very good at maths, with a young man from a less privileged background. And it just really it did the work, you know. It showed him just how privileged he was without us saying it, without his parents saying it. He needed to hear it in his own way.
Adam Fisch:Yeah. It's a wonderful thing, and I love in the examples you gave, you know, it sounds like the program is also so adaptable to what the individual's needs are, which is such a wonderful thing.
Jess McGawley:Thank you. No. It really is. We've found that's the best way because don't get me wrong. There are lots of commonalities between the young people we work with. But like I said at the start, this is all about their identity forming years, and you have to meet them where they are no matter where that is on the journey.
Adam Fisch:Jess, thank you for such a wonderful discussion. We'll link to Dallington in the show notes. You know, it it is a unique offering. I hope at the risk of it maybe being competition for you that it becomes less unique in the future because
Jess McGawley:Absolutely. I agree.
Adam Fisch:Such an important, addition to the space. So, it's really wonderful. And, yeah, thanks for taking the time.
Jess McGawley:Thank you so much.
Adam Fisch:Thank you so much for listening. Our Family Office is Canada's first purpose built shared family office, and the Our Family Office podcast is produced by Henry Shew. Please visit ourfamilyoffice.ca for more information about our firm. And don't forget to rate, review, and subscribe so you don't miss an episode. And of course, share it with your family. See you next time.
Adam Fisch:The information in this podcast is presented as a general educational and informational resource only. While certain participants in this podcast may be registered to provide investment advice as a representative of Our Family Office, Inc, itself a registered firm in certain Canadian jurisdictions, this podcast does not provide individualized investment, financial planning, legal, tax, or insurance advice, nor is it meant as a recommendation to any listener to buy or sell any specific securities or otherwise take any other investment action? Any action you may take as a result of the information presented in this podcast is your own responsibility. Our Family Office Inc.
Adam Fisch:And each of its representatives that participate in any podcast disclaim that any listeners should rely in any way on any of this content as investment, tax, legal, or insurance advice. Listeners are encouraged to consult with their individual investment advisor and other financial professionals prior to taking any potential investment actions or making any insurance or tax decisions.