Still Yours to Shape: Reclaiming Identity in Times of Transition

Welcome to Legacy Builders, strategies for building successful family enterprises. Brought to you by Beacon Family Office at CI Assante Wealth Management Ltd. 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 Amy Stein, Chief Impact Officer at Generations Trusted Family Business Advisors. For over 20 years, Amy was a vital part of her family’s 4th-generation business, Henry’s, Canada’s largest independent imaging retailer, where she gained firsthand insight into the realities of family enterprise. Most recently, she led the launch of the Foundation for Henry’s, using creativity as a powerful tool to support and promote mental health. Now, she helps family enterprises design philanthropic strategies that reflect their values, engage the next generation, and leave a lasting impact.

My goal is to be the most curious person in today’s conversation with Amy. We’ll explore how transition feels from the inside, when leadership, legacy, and personal identity all converge. Amy brings a perspective shaped by decades inside a family business, a foundation built with purpose, and an unexpected shift that raised bigger questions about what’s next. Together, we’ll look at how experience becomes its own kind of preparation, and why resilience, reflection, and voice matter in moments of change.

Now, let’s dive in!

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

Amy: Great!

Cory: Amy, imagine you’re delivering the commencement speech to the graduating class of 2026, 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?

Amy: I think that’s a great question, and a loaded question. But I think I would start my speech by saying, well, we all have our own experiences, everything that we’ve learned in university and graduation, and while we’re sitting here, looking into the future, is making sure that you apply your skills. You can apply them to any job that you do. And that is professionally, personally.

I think the idea that the job that you have today or the job you’re about to get, it may not exist, and that you sometimes you need to be ready for the unexpected, because you can be doing a job one day, and maybe the next day, you’ve got something else, and it’s totally different. And so I would really encourage people to use their transferable skills, and really understand why they’re doing the things that they’re doing. I think it’s not enough now just to go through a textbook anymore, that you really need to understand what you’re doing and how to analyze. And I would say probably the most important piece is building relationships. I think without that, it’s pretty tough, and I think the importance of building relationships can’t be underestimated.

I also thought that coffee would never be part of my job, and it’s a huge part of my career. And it’s sort of where I’ve gotten to today, is because I’ve had a lot of coffee, and I’ve talked to a lot of people. And it’s sometimes a great conversation, sometimes they’re not, and that’s fine. But you might see them a couple years later saying, remember that conversation that we had? Let’s talk about that again. And it’s happened a fair bit. And I just think the idea of just being personal, and having people know that you’re approachable, and the human side of it, I think is really the most important to me.

Cory: I love how you positioned those transferable skills as something that isn’t just a career skill. It’s something that’s used across our entire lives and in different roles and different scenarios. And so as you think about some of those skills, and maybe even how some of those skills are developed, what is it that really resonates for you, that you’ve been able to acquire along your career?

Amy: I think for my career, it definitely has not been a straight line. It’s probably been the windiest road anybody’s ever seen. My resume does not follow a normal pattern by any means. But I think that’s actually the joy of it, and all the different experiences that I’ve had. So when I’m dealing with a problem, or there’s something going on, there’s usually a way that I can relate to taking a piece out of the many jobs I had, to say, okay, a lot of the jobs actually that I had in our family business were because we didn’t have anybody to do it. And I’m like, okay, let me figure this out. And there was a lot of that.

And because the company was sort of, we were entrepreneurial but pretty scrappy, small budgets, okay, how are we going to get this done? And it still has to look professional, and it still has to be sort of the Henry’s, or I’ll say the Henry’s way. But you learned a lot of determination, and how to think creatively about how you’re going to solve the problems, and how are we going to do this. So I think a lot of that is sort of what I’ve taken with me.

Cory: And so when you think of young individuals in family enterprises who are thinking about that textbook that they’re about to read, or all those textbooks that they did read, what is it that really stands out for you in those learning structures that we have, that really pulls us to the future with some of that?

Amy: I think for me, the piece about it, you’re always learning. There’s always a better way to do something. Nothing is ever going to be perfect. You can spend your entire life trying to be perfect, and you’ll never get there. It sort of is, is it good enough? I think what I’ve taken away from my learnings when I was reading textbooks and all of that, I’m aging myself by saying, those are the days when you had to memorize things. But I think it’s the idea that you want to learn. You always want to do better. It doesn’t mean you’re not satisfied with what you’re doing, but there’s always a way that you can do it better. And I think, for me, it’s also the idea of, you know what? I keep taking courses even though, sure, I did a graduate degree, everything. I’ve got twenty years of experience, everything. There’s still a lot of things I don’t know. And the idea that I decided to take my family enterprise adviser course. That was a huge step. I sort of hummed and hawed about it for probably easily six months deciding, is this what I want to do? Even after I exited the business, I took the governance essentials program from Rotman. And the ICD is on my list. So if there’s always something coming down the pipeline that you’re looking at, and there’s always things that you’re reading about that you’re interested in, that you could maybe apply to your position and your job.

Cory: And, Amy, when you say that it needs to be done the Henry’s way, what does that mean as a family brand to you? And how do you see other families developing their way of doing things?

Amy: I would say, the Henry’s way, I mean, there’s no real definition of it. We weren’t that formal, especially in the early years. But I would say the Henry’s way was whatever you were doing, you did it properly. And you did it to the best of your ability, and with all the information that you had at the time. So you make the best decisions you can. I also said we did things with smaller budgets. It wasn’t a massive conglomerate where you had massive marketing machines and all these other things where it was a million dollars, like, that’s fine, I’ll do it for one campaign. We didn’t do that. It’s, okay, I’m going to print a coupon. I’m going to do it this way, then we’re going to have the vendor show up. We organize it. And we all rolled up our sleeves to get things done. And whatever you needed to do, you just did it. It didn’t matter what your job was. and what level you were, you just did it. And you made sure that things were organized so you weren’t wasting people’s time, and you weren’t wasting your own time.

And I think that you wanted the customers to come in, and you wanted them to be happy, relaxed. This is supposed to be a happy place where it was a trusted brand. It is a trusted brand. We’ve been around for a long time, and people knew us for the product, the customer service, and our product knowledge, and that’s sort of what we lived by.

Cory: If you think back to your earliest memory, and as you were explaining that, I thought of the word resourcefulness. And if you think of that, where was that started to be instilled in you in the earliest days?

Amy: I think for as long as I can remember. I don’t remember ever not trying to be resourceful. I think also, my dad, Andy, who was third generation, he’s very methodical. We always call him the human calculator. He could spot a mistake from a mile away. We called him eagle eyes. And he knew that. So we said that to his face.

I think that you made sure that whatever resources you had, or maybe you know somebody who knows something about this, you’re like, well, I’m going to give them a call, and let’s chat about it. I’m going to tell them my idea, and maybe they can poke some holes, or tell me, is there something I should be doing differently? But you sort of use the resources and the people that you knew to help guide you if you didn’t know all the answers. And everybody does not have all the answers.

Cory: And, Amy, when you mentioned about the job that you’re about to have might not exist, tell us what that really means to you, and some of those curveballs along the way, because I know there’s a few.

Amy: I think that’s a very good question. I think the idea that you don’t always know, like, you think you’re going down one path. I started in the family business long before I was in university. There’s a picture of me when I was, I think, 10 or a month old, in our church street location, which was the flagship in 1974. So everybody knows how old I am now. And I’m 51. And it was in the middle of the construction. So they just put down a baby blanket for me, and there I was. I guess that’s what you did with your kids at the time. We would wrap them in bubble wrap, and they would never be there. But at least they gave me a blanket.

So that was sort of the good part of it. I feel like I had the luxury. I was in a playpen at the same age in the family business. That was fancy. And I think, sorry, can you repeat the question again for me?

Cory: Yes. So, curveballs.

Amy: And so I think you start off on one path. I was really interested in sports marketing, sports in the business, and sponsorships and events. That was my thing. I volunteered at the ‘96 Olympics. I was in the sponsor village. It was fantastic. It was a volunteer job, and it was the best job I ever had. I sort of went down that road, and I had a bachelor of recreation and sports marketing. I think my dad was like, what is that? Couldn’t figure out what it was.

I worked in New York for a summer. I did a whole bunch of stuff, and I think I still take the same skills that I had then today. I was still determined. I was still stubborn. It was all the same skills. But I think when I graduated, it’s just like, I don’t think I like the jobs yet. So I’m going to go back and I’m going to do my MBA. And I looked at a few different programs. And I was at Dalhousie in Halifax, and I got in right out of undergrad. And I decided I’m just going to take the opportunity because it might not come up again. And so I took it, and it was another two years. But I’d say I’ve learned more in those two years than, I mean, I learned a lot in my undergrad, but I really learned, what I would say the more formal side of the business was about. We’re making deals, and my dad went on buying trips, and I’d hear about stuff at the dinner table all the time, which, by the way, it’s amazing what you can learn at the dinner table.

So, I sort of did that, and I said, okay, great, I’m going to go and get my MBA. And it was something that I was really happy that I did. It was a lot of work. I still remember when I graduated, my parents were sort of hanging off the balcony like the Muppets, cheering. So, probably because I called them every day and I was like, is this over yet? And I think that set me up for being able to do the jobs that were sort of coming to me, and being able to say, if I don’t know how to do this, I’m going to figure it out. Because I had the formal training, the formal background, the processes, and the educational side behind me. But then I also had the entrepreneurial side where you could actually do stuff.

And yes, there were some curveballs. There were a couple times, my job changed about every two years. So I moved through the business and learned how every department operated. I did know how IT operated, but you didn’t want me fixing your computer at the time, and I was the one who broke the photocopy machines when you did have them. But I sort of went through, and even in accounting and finance which was not my background, we were changing banks. I learned how to do all of that piece. So you learn how to read the financial statements properly, what’s normal course in business and what’s not, so you’re not making these crazy decisions.

I think the curveballs come with changes in the industry, changes in the economy, tsunamis, you know, fires on boats on shipping containers where you have inventory. I’ll say the last curveball was when we sold the business. And that was June 2023. And at that point, I was leading the foundation, which was the Henry’s Foundation then, which is now called the Pixel Foundation. And I was a Henry’s employee. and but still very much ingrained in the business. And that was my passion. That’s what I knew. And then a few months later, all of a sudden, June 30 is your last day. And all of a sudden, you know, the foundation becomes a labor of love. It can’t be your full-time job anymore. It’s a labor of love, but it’s still something that I absolutely love, and so I still keep it.

I’d say the next curveball came out six weeks later. I had a heart attack while I was riding my bike about forty-five minutes north of Toronto by myself. I think that was definitely a curveball. That’s probably the biggest one I ever had. I had to slow down, and I just needed to take time off to take care of my health and figure out what I was going to do next. And that’s where it became a longer process to say, what’s next now? A heart attack at 48, I would say is definitely terrible, and it’s one of those things that’s totally unexpected. But you deal with it. You go to rehab. You do what you need to do. And I was insanely lucky to be sitting here today. So I think just trying to take things in perspective.

Cory: And, Amy, going back to the stories at the dinner table. So thinking back, what did those stories sound like, and how did they influence your relationship with the business?

Amy: I’ve been hearing about them since I was a kid. And because my dad worked six days a week, probably more when he was home, we always had dinner, usually around 07:00, which was later, because my dad had to close the shop. It was a one-store operation then. And his real passion is a merchant, the deals and the purchasing. And he’s good at it. He’s still really good at it. So if you need him to negotiate anything, that’s where I learned. He would come home, and him and my mom would talk about it. They talk about stuff. It was the normal course of conversation. It wasn’t anything special. But I think his kids, for my sister and I, it was just normal. This is what we heard. So you’d hear about whether there was a buying trip, or what happened, or what this person said, or there was something going on at the store today, or my dad got called in the middle of the night because the alarm went off. There was always something.

Christmas back then, that was the busiest time of the year. You didn’t see anybody in my family for at least a month or so. And I would go in and pile the boxes high, because you didn’t have big warehouses then. And that’s how it worked. My whole family was involved, even my grandmother on my dad’s side. So I would also learn from her at the table. And my uncle was in retail. Everybody was sort of part of it. So there were no boundaries.

Cory: Let’s talk about that moment when that announcement came about. What did that look like in the family? And then we’ll talk about a little bit of the impact on you. But what did that look like as everybody who had so much of themselves and the family tied up in that business?

Amy: You’re referring to the exit, like the announcement of the purchase of the acquisition?

Cory: Exactly.

Amy: I think by the time the acquisition came, there were very few family members left in the business. So my uncle and I had retired. I did have some cousins in it. They had also either moved on or retired too. And so it’s my parents, my sister, and I. And my sister was a CEO at the time when we were selling. I still had a few cousins in the business as well, but it was really the four of us.

I think that you always know the day is coming at some point, but it never really occurs to you that it actually might happen. And you just keep going. At the time, I was 48. I was like, this is my career. This is what it’s going to be. And I was happy with that. I was quite happy with my identity and who I was, and the people I was able to speak with, and people that I had met, and sort of all the different levels of the company that I had worked at, which I think also gave me a unique perspective on just sort of how companies run. And so I think, sort of taking that, I think it was a big shock. I knew it was coming, but it was still a big shock to me. And it was a very big shock, I think, to a lot of our employees, we had 300 employees at the time, and also to my family as well. So, like, my extended family, because it had been a part of us. It was my great grandfather that started in 1909. So it had been in the family for a hundred and fourteen years. So it’s really hard then to say, okay, this is what’s happening. And all of a sudden, I’m not going to be there. We’re not part of this anymore. It’s a very strange feeling.

Cory: For sure. And so, Amy, when you say I knew that it was coming, was that inferred, or were you actively part of those conversations that the business would be sold?

Amy: So I was part of the conversations, I guess, the family deciding that we’re going to do this. I was not involved directly with the private equity group that purchased us. I think my sister, my CFO, and my dad were more involved in the details of it than I would have been. I heard all about the details, most of it, but that was sort of after effect while it’s going on, but I was not sitting at the table then. But I was well aware of what was going on. So I sort of knew that this was coming, and I knew I might be a part of that. Sort of going, okay, this is happening. We don’t know what it’s going to look like. It’s the transaction. But then there’s the piece that nobody talks about is, well, what’s next?

Cory: So it was a thing that you knew was coming, but was it really more everyone focused on the transaction? Was there anyone thinking about what’s next?

Amy: No. It was a transaction. So everybody was very focused on, okay, this is the task at hand right now. Whatever happens after, we won’t deal with it. And we had talked to a few potential purchasers. One, I think, wanted to sort of rip the business apart, and there would be nothing left of what it was known for. We also had 300 people. And that was something that was very important to us, that they don’t lose their jobs. And so we went with somebody, obviously, who kept the business intact. And so as a customer today, I don’t think he would know that it’s different owners. So it’s still the same people running it. And it’s a lot of the same staff.

I think you sort of have it in the back of your mind saying, it’s coming, but I’m going to deal with that later, but it’s just it’s in the back. You’re sort of so focused on what you need to do right now to get to that point.

Cory: And the preparedness, what did that look like from the advisers and professionals around the family and the business?

Amy: I think it was a lot around the transaction. My job was sort of up in the air, and sort of how the foundation was going to work, and what was going to happen after, and I didn’t know. I mean, nobody buys foundations. It’s not part of a sale.  It’s really unfortunate, but it’s not. And so what was that going to look like? You start thinking about it. Well, okay. It could go this way. It could go that way. But it was really about the transaction. It was okay. Obviously, there’s the due diligence. There is all the paperwork. There are all the other pieces that go with it, but it’s always the human side that sort of gets lost. And I don’t think a lot of acquisitions actually always go that far. So it’s sort of the piece that nobody really talks about. Sure, they’ll give you resources for transitioning out, but leaving a family business as a family member after twenty-five years, after your entire life, and leaving as an employee are two very different things.

And so, a transition specialist, I think the majority that I would have been referred to at the time, that’s not their specialty. And so a corporate executive at a public company, or even a private company, but it’s not there’s no relation. So it’s it’s it’s a lot different, I think. And I think the skills to sort of move through that piece and through that progression, are very different.

Cory: And coming to your decision to become a family enterprise adviser, what if you were to take your magic wand and say, what I know now from education and experience, what could there have been in 2022, 2023, in preparation for this big event?

Amy: I think knowing what I know now, and we did have an FDA with us. But I think as we got sort of closer to the end, probably not as much. And I think just because we were all so busy with the transaction, none of us had been through this before, so we just sort of kept going our merry way. But I think knowing what I know now, and with the FDA, I think there are times where I would have spoken up more, but I think I would have spoken up with more confidence about what I was talking about. And I think sort of knowing some of the people that I have met through the FDA, and yourself and the symposium, and all the other people that I have met in the courses, I think just about, yes, this is how it works. Here’s the process and what happens. There’s some anomalies, and this is also what happens.

But even having I think, somebody says, I’m an exit specialist. This is sort of what I do. Or having people there and just going through the framework to say, these are all the things that you really need to think about. But I think for me, it was saying, no. This is why the governance piece is so important. This is why this is important. And it’s not that I think that we did anything wrong. I think it is just me thinking now. And I said this to my dad. I remember saying we missed a couple things. If I would have known this, this is what I might have said, or this is maybe how I would have advocated.

So I think there are definitely things that I know now that maybe I would have done differently. And that sort of comes back to the, well, you keep learning. So I say with you know, I’ve got my new advisory firm that I launched, Generations. And I know I’m jumping around here. But that’s sort of why I’m doing this, to say, hey, I’ve been through this. I’ve been in my client’s shoes, and I’ve been on the family side to say, here’s some of the things that I would have liked, and where I could have used support, so let me help other people do the same. And I think that’s really one of the main reasons why.

Cory: And I think about the three circle model. There’s always these conversations of, is there a missing circle? And I’m thinking about that individual circle and where that plays. And so thinking about that, what do you think could be done if somebody was really thinking about the individual as going through an exit or transition?

Amy: I think it’s the three-circle model because, I think the first time we sat with my family’s FEA, that was the first thing that they showed us. And then when I sat down in the class the first day, I was like, I know this. So I was like, I get it. I understand it. I mean, I obviously understand a little bit more about it now. You talk about the family and the business and the ownership side. There’s the family. But you’re right. There’s the individuals within that, within each of those circles. And I think how each individual contributes and how they feel about a certain decision, I think being part of the process of the decisions is way more important than what that actual decision is.

And I think because there are so many, there are feelings and there’s emotion, you remember something about your sibling from grade two, and because they bothered you then about something, somehow this all comes back to you, whereas you wouldn’t have that in a normal business conversation. But these are sort of the things that they’ve sort of formed your opinions and sort of who you are and how you react to things. And I do think you’re right, that there is the individual within those circles. And maybe it’s a separate circle. I’m not sure. But within the circles, I do think there’s the important piece of the actual individual there.

Cory: And that progression of identity, what is it that you would tell your younger self as it relates to how your identity transitioned and shaped by experiences?

Amy: The loss of identity was probably the toughest part, going through the exit. And you sort of think, it’s going to be a little bit bumpy on the other side. It’ll be fine. And then all of a sudden, you get to the other side, and it’s like you were thrown off a cliff. And you’re like, what now? There you go. You’re on your own. But the loss of identity I think was my mistake. My identity was tied to the business, and it was tied up within it. Everything that I did, somehow revolved around it, or people knew me from Henry’s.

And when I told them what I did, whether when I was working on the corporate side or when I was doing the foundation, people knew the business. They knew me. It was trusted. It was something you’re very proud of. And it teaches you a lot about pride. You’re always on because you’re always representing the business and your family. And it’s something personal. And I would say maybe not having your identity totally tied to the business, which is really hard to do, would certainly be my suggestion. But it is a pretty tough thing to do. I did have other interests outside, and I did lots of other things outside the business. But that was my identity.

And so when you move on, is to say, okay, I was still part of this. It was still a huge part of my life, and now I’m going to go find something. I’ve got to find something else that will match that. I don’t think it’ll ever match that, but something pretty close to that.

Cory: And Amy, after the business had sold, did the way in which the family conducted business change? Did you feel that that identity of the family? Because I think a lot of families don’t realize there’s a lot of legal financial structures that are going to hold us together, that we’re still making decisions together after we sell and operate in.So, thinking about that identity and some of the actions, did that shift?

Amy: It did. I was also used to seeing my sister every day, and even though my dad was not involved in the business on a daily basis at that point, I still saw them a lot or talked to them a lot. So it’s because those conversations sort of dwindle, you don’t see them as much. You probably still see them a lot as a family member, but not to the extent of what you had before. And you don’t have those conversations with business because they don’t exist. But, yes, you’re definitely still tied together. And I think the impetus for that actually for me was the first day that I walked into the FEA course in Calgary, in May 2024. And I think it was David Bentall, he asked, what’s a family enterprise? Are you part of one? I’m like, no. We sold. Of course, I’m not. And then he starts going through all the things, and I’m like, wait a second. Maybe I am. You’re not totally over. It’s still there, in a different form. And I was like, okay. I guess I could still be a family business. It was sort of eye opening about how many areas the family touches, and sort of what’s involved there.

Cory: Absolutely! Amy, as we near the end of our conversation today, there’s a few questions I ask each guest before we wrap up. Are you ready for the tough ones?

Amy: I think so. Yes. I’ll try my best.

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

Amy: It is having, I think, one that has a shared purpose. You know where you’re heading. Having people going off in different directions doesn’t really help too many people. But it’s also knowing what your role is. And I’m always a big fan of sort of the clarity of your role and what those boundaries are, because I think you can sort of ruffle a lot of feathers doing that, going over the lines. But I think it’s sort of knowing what your lane is. Like, this is okay. This is what we’re good at. This is not what we’re good at. This is our purpose, and this is sort of what drives us forward. And I think that’s sort of the piece that I think is very important.

Cory: I appreciate that there’s so many things that go on undiscussed. Just defining those a little bit goes a long way for sure.

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

Amy: The first thing is, I think, being grounded, is that money solves money problems. It doesn’t solve other problems. It doesn’t solve relationships. It doesn’t solve other things. I still go back to having a purpose, that and the importance of having your kids grounded. And the parents too. All generations actually. Money is one thing, but I think it’s what you do with it, what’s the purpose of your wealth, and knowing what that is, because there’s a lot of good things you can do with it. The idea of treating people with respect, and really just having the qualities that makes being a good person. The money is one thing, but I really think it’s the people.

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

Amy: I always go back to this with the people and the purpose, and I know I’ve talked a lot about that. So I’ll leave that one aside, but I do believe that’s part of it. One is being open about your communications. You want to be approachable. I think the older style of leadership is sort of the command and control. I don’t think that’s necessary anymore.  I personally don’t think it’s the right way to go. And I think that there are so many different perspectives now, and there’s information coming from everywhere.

So I think it’s filtering out sort of the information you need, information you don’t need, and making sure you have got the right people in the room with you, because you don’t want to be the smartest person in the room. You want people who know more about certain subjects than you do. You will never know everything. I think it’s the idea of actually trusting your people and listening to them. So to me, I think that’s the piece. It’s the different perspectives.

Cory: Love it. Yes, if you’re the smartest person in the room, you might be in the wrong room, or you didn’t invite the right people.

Amy: You don’t need you don’t need anybody else, though. So I don’t know if you’ll get that far, but you’re not going to need anybody else.

Cory: Great! And before we conclude our discussion, I’d like to highlight where our listeners can engage in more conversations that you’re having, or maybe some resources that you think are important to the conversation we had today.

Amy: I would say in terms of the resources, I like to take a different approach to things, and I go back to the people. It’s about combining the business with the family, with the philanthropy side, and the purpose of your wealth.

I’ve got my new firm, Generations, which is launched. So there’s some information on my website about that as well. But I think in terms of resources, Family Enterprise Canada has a number of really good resources on there. I attend their events so I can meet people and hear other people’s stories, because it’s amazing when you hear people’s stories about how close they might be to yours. And until one person opens up, you’ll never know.

For me, the resources, it’s getting out and meeting people. It sort of goes back to the coffee, which I never thought was going to be part of my career, which is a huge part of my career.

Cory: Absolutely! And we’ll make sure to include links in the show notes to your website so our listeners can find you there. And, Amy, 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 just didn’t get a chance to touch on?

Amy: No, I think we’ve covered a lot of ground. I was really excited to be here, honored to be asked to be on your show. I sort of listened to a few of the podcasts that you have done and the people that you’ve interviewed, so I’m quite honored to be among them. I’m really happy to be here. So thank you.

Cory: Awesome! Well, I’m so glad that you are now one of those people. I appreciate you taking the time to share your expertise, your experiences with us, telling those stories, sharing with others. My hope is that there’s one key takeaway for each person who listens, and it’s not the same takeaway for everyone. So, thank you so much. I’m grateful for you to have joined us, and for all the contributions that you’ve made to this episode.

Amy: Great, thank you very much, I appreciate it!

As we wrap up this episode, we invite you to reflect on Amy’s perspective on transition as a moment where experience, identity, and uncertainty intersect. Her story reminds us that change often asks us to slow down, take stock of what we’ve learned, and consider how those lessons shape what comes next.

Whether you’re part of a family enterprise or work alongside enterprising families, her perspective brings attention to the human side of transition, where voice, lived experience, and personal identity carry real weight. It’s a reminder that meaningful preparation includes space for people, not just process.

Throughout our conversation, Amy offered a candid look at what it means to move through transition from the inside. She shared how experience, learning, and resilience are shaped over time and how moments of change can challenge identity as much as direction. From navigating uncertainty to finding meaning beyond a long-held role, her reflections invite us to think more intentionally about how we prepare for change, and how personal clarity plays a vital role in shaping what comes next.

If Amy’s story has sparked something for you, her new firm, Generations Trusted Family Business Advisors, offers a unique perspective at the intersection of business, family, and philanthropy. You’ll find more about her work, along with her contact information, in the show notes.

Disclaimer: 

This program was prepared by Cory Gagnon, who is a Senior Wealth Advisor with Beacon Family Office at CI Assante Wealth Management Ltd. This is not an official program of CI Assante Wealth Management Ltd, and the statements and opinions expressed during this podcast are not necessarily those of CI Assante Wealth Management Ltd. 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.