Designing the Next Chapter: Retirement Planning for Purpose, Identity, and What Comes Next

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 Susan Latremoille, Co-Founder and Partner at Next Chapter Lifestyle Advisors. With more than 35 years as a wealth advisor, Susan spent her career helping clients prepare financially for retirement, while noticing a consistent truth. Having enough money was only part of the equation. It was the non-financial side of transition that most often determined whether retirement was truly successful. Today, Susan focuses on supporting individuals, business owners, and advisors through those pivotal life transitions. As a Certified Professional Retirement Coach, Certified Exit Planning Advisor, and Family Enterprise Advisor, she helps clients look beyond the transaction or career exit and intentionally design what comes next. Her work centers on clarity around purpose, values, and lifestyle priorities, so retirement is not just an ending, but the beginning of a meaningful next chapter.

My goal is to be the most curious person in today’s conversation with Susan. We’ll explore what it really takes to shape a fulfilling next chapter beyond the wealth plan. From rediscovering old interests to forming new connections outside of work, Susan invites us to look at transition as a time not of slowing down, but of reshaping how we live and grow. We’ll also explore how curiosity and continuous learning can spark direction, meaning, and momentum right when life starts to feel wide open.

Now, let’s dive in!

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

Susan: Yes. I’m ready, Cory.

Cory: Susan, 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?

Susan: First of all, graduates of 2026, congratulations on achieving this educational milestone. And what this does is leads me to the first life lesson that I learned along the way that I’d like to share with you. And that is that just because you’ve graduated doesn’t mean you stop learning. I believe in being a lifelong learner and taking advantage of every opportunity that comes your way to add credentials, to learn something new, to explore in different fields of interest. And all of this, even though you can’t always see it at the point that you’re taking this course or studying something new, you may not be able to see the linkage right away. But looking back over my career, I can certainly attest to the fact that everything I studied, everything I’ve done has all added up then to provide a journey and a career path of success and hopefully significance. So just because you graduated doesn’t mean that learning stops, and I really encourage you to continue your education either formally or informally.

The second thing I’d say is that we need problem-solvers in this world. And so if you see a problem out there in society or in the workplace, tackle it. Try and find a solution to that problem. And that will give you purpose and meaning in your own life, and it will be of inordinate help to other people.

So let me just explain where these two main pieces of advice come from in my own journey. First of all, I graduated with a general BA from University of Toronto. And it wasn’t until I discovered the financial services industry that I started to get really serious about more specific education. That led me to do an MBA. Then I got certified in all the usual investment courses that people take. And along the way, then I also did became a portfolio manager and did the family enterprise advisor program, the ICD, when I was appointed to a board of directors of the parent company that I was working for, and then more recently became a SEPA, a certified exit planning advisor through the Exit Planning Institute, where I’m now on the faculty of the Exit Planning Institute, teaching personal planning.

So when I look back, if I hadn’t undertaken these courses and credentials, I never would have got to where I am today. So that’s been a bit of my life journey. As far as the problem-solving is concerned, like many of you, I was a financial advisor, in fact, for thirty eight years, a wealth advisor, in fact, going beyond just strictly investments, but also helping clients with wealth planning. And what I discovered in working with many business owners and successful professionals is that many of them were focused on amounting and amassing the wealth that they needed to retire comfortably. All the focus was on having the financial freedom to retire. But what I started to notice during my career was that many of them were not as happy as they thought they would be when they finally did sell their business or step away from their career or profession. And I thought there’s something wrong with this picture. If I’m priding myself on taking a holistic approach, why am I not tackling the issue of this major life transition that people call retirement, or we like to call it rewirement, because I really don’t believe in retirement if you’re going to be a lifelong learner.

So that’s what really prompted me to sell my wealth practice and focus on the nonfinancial side of this major life transition historically called retirement, now called next chapter or rewirement. So you can see the linkages then between the two main pieces of advice that I’ve given you and how they have helped me along in my journey. One is to be a lifelong learner, and the other is to see a problem and do something about it.

Cory: Amazing. And Susan, when you think of that lifelong learner, what is it that that truly makes somebody, have that curiosity to continue to learn beyond just the letters, or paper, or things that maybe traditionally in society, and in the formal education system that we find?

Susan: Now you mentioned the word right there that I was going to use, and that is curiosity, to be curious about a wide range of subjects. And sometimes not knowing what you’re going to be learning, how well it’s going to serve you in the future. But to continue to learn and experiment with new things, I mean, now we’re in the age of AI. So, again, we all have a learning curve to learn how to use artificial intelligence, ChatGPT, and so on. And so to be a continuous learner is to be able to tackle new technologies, new ways of doing things, and your word, curiosity, to keep moving forward.

Cory: And as you work with people who are approaching that next chapter, what is it that changes in the way that they’re learning at that stage of life?

Susan: I think that when people are employed either in a career or profession, or where they have their own business or working in business, there’s natural learning that takes place keeping up with the industry that you’re in, with the role, the position that you’re in. But when people transition away from that career business, that impetus to keep learning kind of drops away.

So we believe strongly in the work that we do, that self-development and continuous learning is still very much part of that next chapter. And it may be something completely different than people who worked in a field that they worked in, or what they studied in younger years. But as long as we keep moving forward, learning something new, exploring new terrain in terms of subject matter and opportunities, then I think we extend our longevity. We certainly become more interesting people, and it opens doors that may never have opened to us before.

Cory: And I think of people who have great hobbies and are actively involved in different parts of the community. What do you find when people have really been so focused on career and business that they really are stepping back and looking around and saying, I just don’t seem to have these hobbies or interests, where I can go and learn more about them?

Susan: Yes. I mean, it’s definitely an issue if people have been extremely focused on their career or business that they haven’t had time. They haven’t had the opportunity to explore other things. So this transition stage is a perfect time to experiment with different things, to try new avenues. And that leads me to the discussion of the philosophy that I really entertain, and that is living a rich life.

So really there are three elements that I believe people need to think about as they transition to this next chapter. One is how do you want to live well? What does living well mean to you? And it could be intangible things like family relationships, or tangible things like owning a vacation property, or taking trips or whatever, but living well is the basic.

Then we think about, and you touched on it in your comment a minute ago, about volunteerism. So giving back, give back is the second tenet of the rich life philosophy, and the giving back doesn’t have to be financial. It can be volunteerism. It could be mentoring, teaching, serving in some capacity on a committee or a board. Or if you’re very financially well-endowed, you can also donate a lot of money and make a difference that way. But I think we all feel better when we give something from ourselves to another person that benefits them. We receive it in return.

The third aspect of the rich life philosophy is to leave a legacy. And I find that as people get older, they start to think about that. They’re reading maybe obituaries in the newspaper about people they knew that have passed on, and they start to think about their own purpose and why they’re here and making a difference in the world.

So live well, give back, leave a legacy. And I think when people make this transition to keep that sort of philosophy in the back of their minds and adopt that rich life mindset is a real asset to them. But then a lot of people need more structure than just thinking about things or having a philosophy. And that’s where the work that we do at Next Chapter Lifestyle Advisors, we provide them with a framework, with a model to actually think about their next chapter in each of these eight areas.

Cory: Amazing. And so when you think of the transitional moments in people’s life as they’re really taking that time to reflect, where can that excitement be created? Because I think of some of the anxiety that many people feel. Where can we create that excitement? And that might be internal, or from people around us who are maybe supporting.

Susan: I think sometimes, people definitely experience anxiety around what they’re going to do with all this newfound time when they do make this transition. And that anxiety is quite normal. And there’s also a period of maybe confusion or lack of clarity, which for most people that have been successful in their careers, they haven’t experienced that for a very long time. So through the fog does become clarity, especially if you work with someone that’s going to help you and point you on the right path.

But I think in terms of excitement, we’re all different. And what excites one person and gets them out of bed in the morning is completely different from someone else. So for some people, volunteerism is where their hearts are, and they really want to dedicate themselves to giving of their time and maybe their resources. But for other people, especially entrepreneurs, they’re still wired to do something, to make something, to sell something. So for an entrepreneur to get excited, a serial entrepreneur, they have to get excited perhaps about a new business idea, a new business opportunity, or perhaps finding a balance between the other activities as well as carrying on in their careers or professions. But I do find that people that do something that’s somewhat similar or akin to what they did professionally, they have tremendous leverage of their knowledge and their network and so on to be able to continue to do that.

Cory: Right. And leaning into your comments around problem solving, I find that entrepreneurs are the best problem solvers around. What is it that you find that people are going like, what sort of roads are they going down after maybe there’s been a transition of the business ownership, within the family or externally, and now they’re they’re still excited, but maybe that pressure on that business legacy isn’t necessarily there, but now it’s more of interest. Where do you see people utilizing those strengths?

Susan: Well, it makes me think of my own brother. And my brother went through Guelph in agricultural mechanics, so learning how to fix farm equipment and so on. And so he worked for a number of several years doing that. And then he had the opportunity to get involved in a John Deere dealership. So he became the owner of a John Deere dealership, and he ran that business very successfully. And then recently, in the last few years, sold the business. Guess what he did? He’s back on the tools. So he built a great big shed, and now he fixes combines and tractors and things.

The mechanic was always in him, but then he also became a businessman with that. But for him, going back to what he was trained in initially is providing him with lots of satisfaction amongst other things. He does like biking and he’s a pilot as well. So he has lots of other activities and interests.

And then I think of another gentleman I know who was working in corporate life, but he always had a hobby of woodworking. And so when he transitioned away from his professional life, he turned his whole garage into a workshop. He started making furniture for the house, for friends, cutting boards, you name it, everything out of wood. And that’s giving him tremendous satisfaction at the same time that he’s got the time to play golf, babysit grandchildren, and just kick back a little bit. So those are a couple of examples of people that have one that stayed in their field, like my brother, but just went to a different part of it. And the other, somebody that always had this sort of sideline hobby, but really never had the time to take it on seriously and has now taken that up.

But for other people, it’s not as clear cut, and they need a guide to help them find that path, which is really a series of trial-and-error until you get it right. And I feel fortunate that I was able to be on that path for myself, as I told you with my career as a financial adviser, and then realizing that people need a lot of help as well on the nonfinancial side. So it is adjacent really or similar in the sense that we’re still dealing with building a better life. It’s just the vehicle now is not the money side, the nonfinancial side.

Cory: Right. And Susan, you mentioned your eight areas. I would love to dive a little bit deeper into that if we could.

Susan: Sure. Be happy to. So the eight areas we talk about, we call your Happiness Portfolio for your next chapter. And the eight areas, I like to think of them as asset classes. After all, if we’re calling it a portfolio, those familiar with financial portfolios will understand that there are, of course, asset classes in a good portfolio, and a good portfolio should be diversified and well-balanced. We all know that from the financial side of things.

The Happiness Portfolio is a way of looking at life in these eight asset classes. And just to give you an outline of what the eight are, the first one, that often, that people are just like I’ve talked about a moment ago, is professional. Do they want to stay working part-time on contract, start a new business? What is your ambition or not for professional?

The second is your primary relationship. So this would be your spouse, husband, wife, or someone that’s very close to you. Oftentimes, we find that when people are busy with their careers or business, they don’t have that time that they want to spend with their significant other or that loved one. So investing in that primary relationship becomes even more important.

Same thing holds true for family and friends. That’s the third area of the Happiness Portfolio, the third asset class. And that is, again, how many people do we know that had to sacrifice being at their children’s concert or school play because of work commitments. So now it’s time to really dive into family activities, and maybe rekindle some friendships from youth from earlier days and make new friends. So family and friends, the third asset class.

The next one we’ve touched on already is giving back. So that’s either volunteerism, mentoring, teaching, or providing financial help giving back.

Then, we talk about spiritual and emotional health. So, again, I touched on that with the idea of purpose, having purpose in your life, and maybe taking time to slow down a little bit, maybe start meditating, or do Yoga or Tai Chi, or some even maybe organized religion, but something that fosters that spiritual aspect of being alive.

Of course, self-development, and I’ve talked about that with being a lifelong learner, keeping the brain active and young. It could be learning a new language, a new skill, and many other ways to stay with the brain working really well, that’s self-development.

Health and aging is super important as people age. Stuff in the body tends to start to fail a little bit. So having a good exercise program, having good nourishment, good food, good sleep, that’s all part of it.

And then the eighth area and probably one that most people associate with retirement or the next chapter is leisure. All the golf games, the bridge games, the travel, the activities that you maybe consider to be what you do in your leisure time reading, etcetera.

So these are the eight areas of the Happiness Portfolio. And I believe that someone planning this transition should really look seriously at all eight and make a plan for each of those areas. Because after all, we do need everything we do to be anchored with purpose. So having purpose in what you’re doing, purpose in the learning, purpose in the activities that you undertake, purpose in the people you’re connected with. Purpose is the underpinning to the Happiness Portfolio. So I hope that gives you an idea of the eight areas of it.

And in the work that we do, we actually take people through a process to help them decide and build a plan for those eight areas. We have the Happiness Portfolio Workbook, which provides that guide. And then we help people through by coaching and working with them to build that next chapter in a way that they don’t spend and waste time sort of fumbling around in the dark trying to figure out what’s next.

Cory: Amazing. I’d love to maybe dive a little bit deeper into some of these eight. I’m not sure if time permits us to go into all of them. I’d love to talk a little bit about that primary relationship, because we’ve got this spouse. We professed our love at some point, and marriage was probably somewhere in history. We spent time maybe raising children, building wealth, and now we’re at this point where we’ve maybe got a little bit more time on our hands and we’re looking at each other. What sort of things do you see people do, or or how do you work with people in that sense to build that relationship up?

Susan: It’s a very good question, Cory, because, when things change, it affects a relationship for sure. So for some, it means that they have time together and they’re building on an already strong relationship. For others, it’s a difficult time. And there are really two reasons that I see for that. One is that if they were both busy with their careers, or one with the career, one raising a family, that any of the issues that may have surfaced in the relationship, there just wasn’t time or the necessity to deal with them. And all of a sudden, they rear their ugly head at this junction.

The other issue is that people sometimes have a very different idea of how they want to spend their next chapter. I think of one couple that had an RV, or wanted to get an RV, take it or buy it in Europe, and travel around Europe in the RV. And he had assumed they’d be just gone for up to a year. And she said, there’s no way I’m leaving for Europe for a year. We’ve got grandchildren. I want to see them every six weeks or so. So they had very different ideas of how they wanted to spend their time.

Another situation that I’m working with right now is, actually, she and her husband were in a financial advisory practice. They sold the practice thinking they would stay on. Things didn’t work out. They live on a farm in the countryside. He’s very happy tending to the property, hunting, being outdoors, and she’s lost. She’s saying, I miss my clients. I miss my team. And so for her, it’s been difficult, and they’re very much on different pages with this whole situation right now.

So, sad to say that there is the highest incidence of what we call gray divorce, and that’s people over the age of 50 splitting up. And it’s often because of this disconnect that’s either happened throughout the course of their relationship, or when they reach this junction in the road so to speak, and they take different paths. But we believe that all of that can be preventable through good communication, through good planning, starting early, and staying on the same course.

It’s not really funny, but remember the lockdown of the COVID era? Well, we look at this time of life as the retirement that you never want to live, COVID lockdown period. So in a way, COVID was a dress rehearsal for what you don’t want to have happen. So you touch on a very good point with primary relationships being critically important at this time. And we’ve got to do something about these high divorce statistics, which I think are very preventable with the proper approach to it before it all happens.

Cory: And, Susan, when you think of professional, what does the next chapter look like that includes professional? Is there an answer of here’s how much people step back, or what they’re doing to still maybe stay professionally engaged and, typically in family enterprises there’s a little bit more flexibility, to disengage in certain areas. What’s the answer there?

Susan: So I know it’s challenging for many entrepreneurs and patriarch, matriarch founders to step away from their baby. And really, that’s what it is. They’re giving up their baby to either their children or to an outside buyer. And this can be quite problematic for them because they go through a period of loss of identity of who they used to be. And nothing worse than going to a cocktail party and someone talks about “I used to, I used to be.” So they really have to redefine themselves in terms of identity.

But for sure, there’s an opportunity for people that have been successful to be able to share that wisdom and knowledge with younger generations. So whether it’s with your own family, in the case of a family enterprise, or whether it’s through teaching, mentoring, training, or some other vehicle. There is so much wisdom built up after many years that I think benefits the younger generation. But it has to be just in a way that works for both parties. So certainly, that’s one option for staying involved and using your professional knowledge and expertise. In my case, my work is associated with what I used to do before, but not exactly the same. We’re working with a client right now who sold this company, but he’s staying on the board of directors. So he still has some input, some oversight, even though he’s not involved in the day-to-day operation.

And then, of course, when you come to serial entrepreneurs, they’re not going to stop. They’re going to start a new business and get engaged. And, again, I think of somebody whose hobby was fishing, and then he found out about these fishing rods and fishing tackle. And before he knew it, he was back in business in the fishing industry. So he kind of combined his hobby of fishing with a new business opportunity.

So it can take very many shapes and forms. And I don’t think there’s one size fits all. And there are certainly people that say, I want nothing to do with anything professional anymore. I don’t want to work. I don’t want to work in my field. I’m not interested in starting something new. And so for them, their Happiness Portfolio has seven asset classes. No problem. It’s very individual.

Cory: And in that sense, Susan, have you seen people add other asset classes to their portfolio?

Susan: Such as?

Cory: I’m just thinking if we remove one, and that’s an option that you’ve seen, is there something else that maybe is individual, specific that you’ve ever seen anyone add?

Susan: I think if someone has been, I would put it under the category of giving back, but you could almost say giving back/professional. Because if someone has created a lot of wealth, philanthropy can be a huge area for them. So they could be basically full-time either raising money or helping to direct a not for profit, being part of a foundation, maybe having a donor advised fund, a family foundation, sitting on the board of a charity. So I would say it’s giving back, and it’s sort of professional, but it’s maybe on the non-paying side of professional. So that’s fine. That’s totally fine. But I would say if you were going to create a separate asset class, then maybe giving back slash/philanthropy would be the one.

Cory: Okay. And what does balance in the eight look like? What do you see that be?

Susan: It’s so different for each individual. I mean, some people are very happy with a life of predominantly leisure. You know? They may play sports. They may be involved in bridge, or some other kind of chess club or something like that. So for them, leisure is a big part of it. And I have a friend who curls. She plays tennis. She plays golf. She kayaks. I mean, leisure is a big part of her life, but that’s not for everybody.

And so it’s really a matter of each individual finding the degree that they want to have of each of these areas. Like some people would say to me, Susan, you work too hard. You’re so involved professionally. But it works for me, and I still have time for a lot of leisure activities, and family and friends, and taking care of my health and so on. So it’s really just finding a balance, which is a very individual exercise.

Cory: Right. And you made comment of that serial entrepreneur, somebody who’s maybe exited multiple businesses. In that sense, when do people start thinking about this? I think of the 42-year-old entrepreneur who just sold his third business, and what does next chapter really look like? Or is there a certain time in life where people really come to say I need to pay more attention here?

Susan: You know, I think of serial entrepreneurs. If you asked a room full of entrepreneurs when this started, when their entrepreneurial life started, and you ask them how many of you had paper roots when you were young, a high percentage of hands would go up. And that’s because that entrepreneurial spirit often starts in childhood, often starts at a very young age. And then it’s just part of who they are throughout life. So if a serial entrepreneur gets a big kick out of starting maybe a venture, a new venture, building a company, building teams, selling, finding resources with the idea that they’re contributing to society. Their field is something that is beneficial to a lot of people. They get satisfaction from that. They employ lots of people. They create wealth. I think that at 42, there’s still plenty of time if someone has that serial entrepreneur mindset that they can start all over again and do something new and different.

Having said that, we also know that entrepreneurs have what we call an achievement addiction. And addictions aren’t healthy after all. So if the addiction to achievement is the driving force, then at some point, they’ll become less happy. They’ll become less enchanted with what they’re doing.

Cory: Right. And where do you see the replacement of some of that achievement as it relates to business? Where can maybe somebody successfully replace some of that and find that purpose elsewhere in their life?

Susan: Well, I think if they’ve been really financially very successful, help a person graduate, become a doctor. I know somebody that does that. He provides scholarships for young people to achieve in medicine, and that gives him a lot of satisfaction. Other people may say, you know, I want to keep it all in the family and do things for my family members.

So I think along with being a serial a successful serial entrepreneur comes the wealth that’s being generated. But then I think it can be just as engaging to see that wealth do good for others, that give back piece of living a rich life, the legacy piece of living a rich life, not just the living well, because if they are living well, they probably have a very comfortable lifestyle as well.

Cory: Right. And from a family and friends perspective, one of the things you and I both have learned from Dan Sullivan over the years, and I remember one of the things that Dan said to me. Beyond somebody getting hit by the bus, there’s kind of three reasons that people die: losing purpose, running out of money, and running out of friends.

And so we’ve talked about the purpose component, but I think about the friends and relationships, Susan. What does that look like, in some of the work that you do with people, to really reinforce that?

Susan: A lot of people had good friends when they were young, but life has taken them in different directions. And they maybe haven’t been as close or as in touch with those early friendships. So I’m a big advocate of people going back to maybe childhood friends, school friends, and just touching base, see where they are today. Because when you have a conversation with somebody that you shared a piece of life with, a part of your life with, even though it was many years ago, you can always pick up where you left off.

So there’s definitely a place for old friends. But their interests may be very different than yours at this stage. They may be at a different stage of life or opportunity, and that’s where new friends come in. So people that share the same interests that you have. I hate to use a golf thing, but golf buddies or people that you belong to a service club with, maybe people that you volunteer with, maybe they’re neighbors and what you share is the neighborhood or people that make great travel companions.

So I think we can really, with a focus on friendships, look from the way back to the friendships we had at a younger age to new friends. And I think there is a place for both. As long as you share the same values and some of the same interests, I think that’s the real foundation then for friendships. Unfortunately, a lot of people when they are in their careers or in business, they feel that their friends are their work colleagues. And they haven’t really gone beyond that to cultivate other friendships. And unfortunately, a lot of those sort of colleague type relationships do tend to fall by the wayside unless there’s another reason for them to stay connected. So it’s just a bit of caution for people where their whole world is their work, and all their friends are people they work with. Some of them, of course, will stay as friends beyond the workplace, but many of them will fall by the wayside when the workplace is no longer there. So that’s why it’s so important to cultivate new relationships and new friendships at this stage.

Cory: Absolutely. I’ve heard that in my work, people not wanting to leave the workplace because that’s where all their friends are. And there’s a lot of time that we don’t really think about that, you know, that identity piece, the friendship piece. There’s many more than just the dollars that it provides in our lives. And I really appreciate that component of making new friends, what that looks like, and where maybe people can seek out those new friendships, because oftentimes people don’t think about that in their life.

Susan: And sometimes it’s accidental. I remember a few years ago, I went on a trip and it was a month long trip with a group. It was part of a travel group. And my partner and I didn’t go with the intention of making friends per se. We were there to enjoy what the place had to offer. But along the way, we did meet another couple. They happened to be from Toronto, and we hit it off with them. And since then, we’ve taken a trip to Alaska together. We’ve taken a trip to Sicily together. And we’ll probably do other travel with them. So these are new friends, but we share that love of travel and the sense of adventure that we all have, that we all share. So that’s an example of it wasn’t intentional to go seek out friends, but a lovely thing happened in making friends for sure.

Cory: Fantastic. Susan, 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?

Susan: Sure.

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

Susan: For building a successful family enterprise, to me, it all comes back to relationships. Unfortunately, family enterprise can often be the hotbed for disagreement and for difficulties in interpersonal relationships. So I would say the foundation of a successful family enterprise is to ensure positive, productive relationships with other family members, with team members that work for the organization, with all the advisors that are advising the organization as well. So really investing in the quality of relationships would be, to me, the foundation.

Cory: Fantastic. And what is the most common challenge that you see, or have seen family enterprises encountering when it comes to transition and continuity?

Susan: That’s a big one because the whole question of succession-planning is so topical and so important these days. A lot of people, I would say in the older generation, assume that their kids are going to take over the business. And it can be problematic, either because they don’t have the right skill set, or they’re really not interested, but they feel compelled because mom and dad want them to. And so it can create some hard feelings, perhaps some discord in the family and in the organization. So I think when people are really cut out, or want to carry on in a family enterprise, they should. But if it’s not for them, then everyone should have the freedom to find different choices.

One family that I worked with, they made a policy. It was a multigenerational family enterprise. And their policy was that before anyone could work in the family business on a full career basis, they had to go and do something else. Now that’s not to say they didn’t have summer jobs, sort of doing basic work. It wasn’t anything in head office that was in a leadership position or anything, but sweeping floors, filling inventory, whatever it is. But to actually then step into the family business in the leadership role, their policy was you have to go and earn your stripes somewhere else. The good news was they came back with lots of life and work experience. The bad news is that some of them decided I’m never coming back because I love what I do elsewhere.

So it’s a double-edged sword sometimes with that policy, but I do think it’s important to give people the choice of working in the enterprise, or doing something that might be more suitable for them long term.

Cory: Fantastic. Yes, I think that autonomy within the family is so important to allow people that freedom of choice, and be here because you want to be here, not because you have to be.

Susan: Exactly.

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

Susan: I would say vision. I would equate leadership with vision. That would be number one. Ability to delegate, important because it can’t be just a one-person show. And sometimes leaders have a hard time bringing people into some of the decision-making, some of the progress that the company or the organization needs to make. So delegation, vision, delegation. And then, I’m still an old-fashioned advocate of hard work. I think when the leader is hardworking, it sets the tone. It sets the example for everyone else to follow suit.

Cory: Fantastic. You know, it makes me think of that delegation aspect of having a great team. And when we talk about what it looks like after an exit, your example of the wife saying, my team, there’s also that aspect of I’ve become a great delegator in my life, and now I don’t have these people to maybe lean on their expertise to to support me. So I think that that’s also a bit of a challenge that needs to be addressed in transition planning.

Susan: And that’s where peer groups come in, being part of a peer group. If being super successful, then maybe something like TIGER 21, where it would be ultra high net worth, or a peer group that’s part of a mentorship program. But some kind of peer group, I think, is great for people.

Cory: Absolutely. And before we conclude our discussion today, I’d like to highlight where our listeners can engage more in the conversations you’re having, as well as any of the conversations or resources that might be applicable to our conversation that we had today.

Susan: Sure. Be happy to outline that. First of all, I’m on LinkedIn, and welcome anybody to connect with me on LinkedIn. Shouldn’t be too difficult because we probably share at least one connection somewhere in the world.

Secondly, I would recommend our website, which is nextchapterlifestyleadvisors.com. We have a ton of resources on our website, both for individuals, couples, business owners, as well as for advisors, namely wealth and financial advisors. Lots of programs there for for advisors as well.

And then, I’ve written a few books. The latest one was 9 Steps to a RichLife Retirement: Live Well, Give Back, Leave a Legacy. That book’s on Amazon in hard copy, in audio, which I recorded myself, and in ebook. Sometimes having lots of books to read is a bit daunting, but I purposely kept this short and sweet so it can be easily read on an airplane ride or a couple of evenings, on your bedside tape from your bedside table.

So those are three ways. LinkedIn, our website, and our books. For more depth on the happiness portfolio, my business partner, Mary Ann Osher, wrote your happiness portfolio for retirement. It’s not about the money. And that one also is on Amazon in those three formats as well. So I invite anybody who wants to follow-up with the conversation to reach out to me. My email address susan@nextchapterlifestyleadvisors.com or through LinkedIn. But I love to talk about this stuff, and really enjoy engaging with people on this, and a whole lot of other related subjects like this.

Cory: Great. And I wanted to make sure that we’ve 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?

Susan: I think we didn’t spend a lot of time on a lot of the challenges that people face. We talked about that sort of period of not knowing or lack of clarity about what’s next. And we touched on the issue of identity, and we touched on the issue of purpose. We also talked about social connections, so we covered a few. But for many business owners losing that status, losing that position of power, of being recognized in the community, of being the who’s who, is another challenge for many people. So I would say that this transition is a very important life change. People don’t give in enough credit for how challenging it can be. And I think it’s really important for people to admit that if they are struggling with, figuring out what’s next for them, or finding purpose that they reach out and talk to what we call ourselves lifestyle planners. We’re not life coaches. We’re lifestyle planners. We have a specific process to take people through to help them find what’s right for them in their next chapter.

So I know it’s not cool to admit that, when your friends say to you, you’re retired, you should be the happiest person in the world. It’s difficult for people to admit that maybe it isn’t also rosy. And areas where people want to achieve and progress, they need a coach. They need someone to help guide them through. And I think this life transition just supports that whole argument as well.

Cory: Amazing. I really appreciate the comment around that guilt of I’ve I made it. I’m retired. I got to that freedom point, and the happiness didn’t follow me. How come?

Susan: So that’s such a good point. Especially when others are saying things that maybe don’t resonate. It’s terrible. They’re looking at you with envy, thinking they wish they were you, retired with money and freedom, but only to find that inside they’re dying from the inside out, so to speak. They’re really not that happy with not having identity, purpose, connections, and so on. So that’s where it’s really important to recreate that. And that’s why we like the term rewirement, not retirement.

Cory: Amazing. Well, thank you, Susan, for taking the time to share your expertise, your experience and everything that you brought to us today. Your insights have been extremely valuable to myself, and I know that our audience will also be very grateful for your contribution. So thank you.

Susan: Thank you, Cory.  It’s been great to be here chatting with you.

As we wrap up this episode, we invite you to reflect on Susan’s insight that transitions are opening spaces where experience meets future possibility. In these moments, we’re invited to listen more closely to what excites us, what fulfills us, and what in us might be ready to grow in new directions.

Whether you’re part of a family enterprise or work alongside enterprising families, her perspective invites us to view transition as a meaningful form of planning, one that goes beyond structure and strategy to include identity, learning, and the relationships that support us along the way.

Throughout our conversation, Susan offered a thoughtful reframe of what it means to prepare for life’s next chapter. She reminded us that transition planning is about stepping into a life that still holds purpose and connection. From building new friendships to rediscovering long-held interests, we explored how the most meaningful chapters are often shaped by what we continue to learn and how we choose to grow. Her insights encourage us to think more broadly about fulfillment, and to recognize that our personal well-being is just as essential to a successful transition as any financial plan.

If Susan’s work has sparked something for you, Next Chapter Lifestyle Advisors offers a range of resources designed for individuals, couples, business owners, and advisors alike. You can also find her latest book, 9 Steps to a RichLife Retirement, on Amazon. You’ll find more about her work, along with Susan’s contact details, 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 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.