Andrea Carpenter and Elizabeth Ledoux, co-founders of The Transition Strategists, were mid-negotiation on a business succession deal when Andrea found out she was pregnant — and her real mistake wasn't the timing, it was treating the deal as a fixed event instead of an evolving process. In this episode, they unpack why succession planning has to be built as a journey, not a transaction, and what that shift changed for both of them.
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My guests for Episode #358 of the My Favorite Mistake podcast are are Andrea Carpenter and Elizabeth Ledoux, co-founders of The Transition Strategists. Andrea is President and self-described “integrator,” a second-generation successor who approaches business succession as a human and identity question first, not just a structural one. Elizabeth is Founder and Head Strategist who has spent more than 30 years helping hundreds of families transition their businesses, and is co-author of the book It's a Journey: The Must-Have Roadmap to Successful Succession Planning.
Andrea and Elizabeth were mid-negotiation on their own succession deal — Andrea buying into Elizabeth's business — when Andrea found out she was pregnant. The pregnancy itself wasn't the mistake. The mistake, as Andrea describes it, was her own rigidity: treating the closing of the deal as a fixed event that had to happen on a set timeline, rather than as one point in an ongoing process. That single-year delay ended up strengthening the partnership, giving both women more time to build trust before signing anything.
The conversation moves from their own story into the patterns they see across the family businesses and successions they advise. Andrea and Elizabeth are opposites on paper — she describes herself as a planner, Elizabeth as an adapter — and they talk candidly about where that creates friction and where it makes them a stronger team. They also lay out the two mistakes they see most often in family business transitions: starting too late, and failing to include the successor in designing the transition itself.
Themes and Questions:
- Why framing a transition as an event instead of a journey creates unnecessary rigidity and stress
- The difference between a “planner” and an “adapter,” and how understanding that wiring reduces conflict
- The two most common mistakes owners make when transitioning a family business
- Why successor readiness typically takes five to ten years to develop, not one
- How the “four Ws” — why, what, who, and when — structure a well-designed transition
- Why 70 percent of owners report regretting the sale of their business, and what helps prevent that outcome
- How bringing successors into the design process early heads off family conflict later
- Why owners need a clear “next adventure” before they can genuinely let go
- Book: It's a Journey: The Must-Have Roadmap to Successful Succession Planning — available at beforebuysell.com
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Meet Andrea Carpenter and Elizabeth Ledoux
Mark Graban: Hi, welcome to My Favorite Mistake. I'm your host, Mark Graban. We have two guests today. They are Andrea Carpenter and Elizabeth Ledoux from their company, The Transition Strategists.
Andrea is president, and she also calls herself the integrator, where she helps family-owned and privately held businesses work through ownership and leadership transitions. She is a second-generation successor herself, and she approaches succession as what she describes as a human and identity question first, not just a structural one.
So I think we'll get to talk about that later on. And we're also joined, again, Elizabeth Ledoux. She is a founder and head strategist at the company. For over 30 years, she's helped hundreds of families transition their businesses. She's the co-author of a book, It's a Journey: The Must-Have Roadmap to Successful Succession Planning.
So Andrea and Elizabeth, thanks for joining us. How are you?
Elizabeth Ledoux: Terrific. It's great to be here.
Mark Graban: So I think this is going to be a first. This is not the first time we've had two guests together, but a lot of times people have told separate stories, and unless I'm making a mistake, I believe you actually have a combined story you were both involved in, right?
Andrea Carpenter: Yeah. And I think the root of it comes to me, so I'll kick us off. When you think of coming up with a plan and a transition, and when I call myself a successor, really what's happening is Elizabeth and I were in talks at the time of me potentially coming into her business and starting to buy a portion of that and working with her.
So when we say successor, that's the world we live in day-to-day. But just to make sure everyone's clear, that's kind of what it is.
The Mistake: Getting Pregnant Mid-Negotiation
Andrea Carpenter: And it's funny, because my mistake is getting pregnant, which — she's going to tell the baby someday it was a mistake — but yeah.
Mark Graban: We did it.
Andrea Carpenter: “Well, you were a mistake.” It's so funny, because looking back on that now, it's like, when is the right timing for anything to really happen? My husband and I had sort of been navigating fertility, didn't really think it was going to happen. And Elizabeth and I are at the point of negotiating our deal and getting ready to sign documents, and here I am with my news that I'm pregnant, and things are changing.
While the baby obviously is not a mistake, and starting our family was not a mistake, I think my rigidity in “this is the plan, this is how it's going to happen, this is the way Elizabeth and I are going to work through this deal” was my first mistake when Elizabeth and I think about our own transition. And I know you have a side to that story too, Elizabeth.
Elizabeth Ledoux: Yeah, I think just tagging onto that concept of when is the right time — that goes all the way back into my career. I don't know that when you do or are thinking about a business transition, sometimes you don't have a clue when the right time is. I think it's just about being ready, because what happened is I had done my transition strategy a couple of years before I met Andrea, and I had no idea when I did my strategy, which is part of the book we have — that it's a journey, and we're trying not to make it an event.
But one, I recognized her, and two, I already had the idea that we were going to have to navigate life happening around us. I think sometimes when you wait for the right timing… I'm a big believer in just jumping in. And I'm also a very high adapter. So when I found out she was pregnant, I was like, “Oh my gosh, that's terrific news.” How exciting, knowing that you were going to have a baby — that was wonderful. But then also just recalibrating the shift and the delay. It took us another year, obviously — well, nine months plus maternity leave plus.
And it took us another year, but in the end, I think it was a great year for us to work together a little longer, get to know each other a little better, and really create some of the trust that is the foundation we're working under. So her, I guess you could call it, big mistake of jumping in when you were trying to get pregnant — I think jumping in when you were trying to get pregnant was a great thing, because it all worked out in the end.
Mark Graban: So it wasn't a mistake in that it messed up the deal, but Andrea, did it cause a lot of stress, or have you rethinking any of this?
Andrea Carpenter: Certainly. Something worth pointing out — Elizabeth called herself an adapter. Those are words we use. We have an assessment we use with families so they can understand within their family who's more adaptable and who's more of a planner. I'm a much higher planner. So Elizabeth and I start walking down this road, and I get this idea, this picture of what things are going to look like. And obviously, when you're negotiating something in a transition or a deal, things are likely to change. They're not going to go exactly the way it is in your mind.
I was only 28 at the time when we started talking about me coming into this business and being her successor. I think the core of the mistake here is the premise that I looked at the transition, or me buying into the business and signing that paperwork and starting my payments, as the thing that was going to happen — like, oh, that's the event. And when Elizabeth says “it's a journey, not an event,” that was a huge lesson for me. Now it's much easier to navigate when something comes up and the timing isn't exactly as planned, because I can walk in with that framework.
How Andrea and Elizabeth Connected
Mark Graban: Rewinding a little bit — what was the initial connection between the two of you? And as a follow-up, what was your interest in a business that serves families who are, say, selling a business? Was that part of your background, growing up in and around a family business yourself?
Andrea Carpenter: Yeah. On my side, I was introduced to Elizabeth via Tiger 21. My daughter is a member of Tiger 21, and Elizabeth is a chair there. When I left my full-time job and was trying to figure out what business I was going to start, I knew I wanted to be an entrepreneur of some sort. I wanted to do something with wealth inheritors — the rising generation, as it's sometimes called. I wasn't sure exactly what that would look like or who I'd work with, so I started meeting with people working in adjacent spaces. That's how I got introduced to Elizabeth.
Elizabeth and I started talking, and it was the first time we talked — like she said, she had already laid some of the groundwork for her own transition, about the type of person she was looking for, and she said, “You could be my successor.” That was never in my frame of reference at all. I thought I was going to be an entrepreneur and go start my own business. That was the plan.
And we started to explore — there were so many thoughtful things we did to explore whether it would be a mutual good fit. The crossover between family business succession and being a successor of family wealth is very similar. We also help families with wealth transitions — how parents talk to their kids about wealth they're inheriting. When I look at my own family, there will be roles and responsibilities, actual job functions I'll essentially have to take on, even though we don't have an operating company.
So I loved the frameworks and a lot of those things, and that's what brought me in to say, “Yes, I want to do more of this work,” because I believe the rising generation is obviously the future. That's how businesses and wealth will carry forward into the future. So how do we support that rising generation to be the best they can be, while also helping the owners live their next adventure and their best lives, and realize all the great things they built? The process is really this amazing ecosystem of successors and owners working together to design the future. There's honestly no one else out there doing something quite like this, and that made me very excited. That's how I ultimately decided, “Yes, I want to come in and build this business with you.”
Why Elizabeth Started Looking for a Successor
Mark Graban: Elizabeth, what was your perspective? Did you expect to find someone so young who would take an interest in this and seem like a good partner?
Elizabeth Ledoux: I had no idea when I started my transition strategy and my plan. I was just walking down the road trying to do what I thought would be good for me, walking the road that I help others walk. When I think about the foundation of it, it started with my team saying, “Hey, what's going to happen if something happens to you? What happens to my job? What happens to our clients? Who's going to take over?”
So that was the foundation of starting it, but as I walked through it, I developed a lot of intellectual property, and also purchased some, and added to it. Just the thought of me putting it in a drawer, or somebody in my family stuffing it in a drawer and never having it surface again, made me sad. So I really started to get a vision for what might fit in my life and who might be the right person, even though I didn't know who it was.
When Andrea and I were sitting on my back porch, we sat down and this conversation evolved, and in that first hour I recognized that she was likely going to try to build what I already had built, and if she could take it — being as young as she is, and as old as I am — and do even more with it and advance it further, that would be kind of a dream come true for me.
I'm also a big believer in successors being ready to take over companies. I think the statistic is that only a third of them actually make it into the next generation — two-thirds fail. The business goes out of business, or the new owner doesn't do well. So two-thirds fail, and I'm a big believer that if an owner strategizes and plans and works with and helps that person grow and develop the skills they need, and understand the environment and the nuances of small business — it's not like running a big business, there are a lot of nuances in how cash flow works, who the bankers are, how you handle taxes — if you stick with it and make it a journey, you put the odds in your favor of being extremely successful in a transition.
How the Timeline Shifted
Mark Graban: Elizabeth, what was your expected timeline for this journey of working together with Andrea, and has that shifted?
Elizabeth Ledoux: You know what, it has shifted, and it shifted because of her first pregnancy and the new baby, and now the second one on the way. So we have a roadmap and a timeline. When we finally got our deal done, it was a year later.
My vision was staying in the business for another seven years or so — that's when I built it. Then I met her two years later. It took us two years to get our deal done. Now we're a year into that, so we're five years already. And I don't think I'm ready to quit and leave, and Andrea's building her family and has the opportunity to do that, but my timeline has absolutely shifted. When I thought about seven years, that was my best vision at the time. But reality is it's probably going to be a little bit longer, and I think that's okay.
Mark Graban: How many years are you into it now?
Elizabeth Ledoux: Right now I'm five in, to my seven.
Andrea Carpenter: And part of that is a vision we were able to create together. I obviously appreciate the space Elizabeth is making for me to do other important things, which is my family. And we're not even related — look how much we can take care of each other. This gets exponentially better sometimes when it's family too. But she's created space for me to do that.
Building a Shared Vision for the Business
Andrea Carpenter: More importantly, we got this vision — okay, we have this many clients now, how many families and businesses do we really think we could help over the next three years if we did this together? Because you've been doing this work with families for 30 years and I haven't. I can help with the operational side, growing our team, helping with the structures and a lot of the systems — those are superpowers I'm good at. What if we work together? Could we get to 500 families and businesses helped in the next three years? What would that look like? What would that do for both of us, for both of our families?
There are two sides of this coin. Part of me thinks, “I'm going to price myself out, I'll never be able to afford this business because we're going to make it too valuable.” But on the flip side, there's that abundance mindset — there's potential that Elizabeth and I grow this together, and then something else happens with it that's different from what we initially imagined, but we had this great ride and we helped 500 families, and that's the vision and the dream, and the ripple effects into their communities from that. That was really exciting.
So while there were technical things around timelines shifting, that vision we were able to create together was bigger than either of us could have come up with on our own.
Elizabeth Ledoux: And the other thing to add — some of what shaped my seven-year timeline was conversations my husband and I had had, because part of the work in these businesses is tied into your family. Your spouse, your children — those things need to be taken into consideration when you're figuring out what you're going to do. How is it going to impact the rest of my family, whether they work in the business or not? Some of my seven years tied into him, and now that we're a little farther down the road and have more visibility, he's a helicopter pilot, so he's still happy flying, and he's not ready to go either.
We still have some work to do, but at least we have a vision of a timeframe, and I think that's so important — for the person transitioning and for the successor — to know there are some boundaries, and some conversations that are set to happen when the time is right, and they're solid, not just “someday.” We have some things on our timeline that we can both count on, and I think that's very important for both sides.
Planner vs. Adapter: How It Shaped the Negotiation
Mark Graban: So stepping back and looking more broadly at other businesses and families going through transitions — I do want to first recap a little bit. Andrea Carpenter and Elizabeth Ledoux from The Transition Strategists, a self-described planner and an adapter. Is that mostly a helpful, complementary set of perspectives, or does it ever cause disconnect when, let's say, you want more of a plan, Andrea?
Andrea Carpenter: Both. It's definitely both. The iMap is a really interesting tool. We use it with every business, every family we start with, because it helps you get to know someone — faster, but also more objectively. The data says what the data says. There are always learned behaviors, but this is the way you're naturally wired. So if someone shows up in a conversation in a certain way — especially when Elizabeth and I were negotiating our own deal, getting close to our buy-sell agreement — there were things Elizabeth would push, push, push on, and I'm thinking, “Where is this coming from?” And it's like, oh yeah, she's a pretty high persuader. She's very social. She gets a lot of energy from trying to convince me her way is the right way.
So there are things I can do to manage that, or I can call it out. We can have a conversation about it. It's a good tool to say, “I'm feeling this way — remember, I'm wired this way.” I'm a more internal person; that's where we're opposite. She's more social, I'm more internal. I'm more of a planner, she's more of an adapter. We both have some high analyst, but she's much more of a persuader than me. When you look at these things, it helps put things in context. Sometimes it's not conflict, but you'll feel tension points where those things show up. Having the words to describe what's happening and why helps me show up better, and I think it helps Elizabeth show up better in our relationship.
Elizabeth Ledoux: Yeah. Any team, any marriage, any relationship — father-daughter or otherwise — has what we call natural points of conflict. They just exist, and that's part of being a human being. What Andrea's talking about, the iMap, helps people normalize who they're dealing with and how. It also helps them not only see who the other person is and honor them, but shift their own behavior to show up for the other person, and vice versa. I'm much more of an email person; she likes calling. I'm like, “She probably won't answer.” But she does, and I'm like, “Let's talk,” and she's like, “No, let's not.” But we can work at a higher level and be better partners because of it.
Is a Seven-Year Transition Typical?
Mark Graban: As we talk about other business transitions — one bridge question. Is seven years longer than the typical planned-out framework?
Elizabeth Ledoux: No, it's really interesting. In my whole 30 years, the fastest I've ever seen a transition happen, the transaction closed in just under a year. But that was for tax purposes, and it was really fast — a father-daughter transition that moved quickly. Dad was ready to get out, daughter really wanted in, and the timing, tax situation, and valuation were all right where they needed to be.
I think the best measure — going back to making sure the successor is really functionally ready — takes about five years. And if you don't know who your successor is yet, just identifying that person can take longer. If you're navigating employees, or bringing in a son or daughter who might be 25 or 30 years younger than you, the age difference and experience difference create a steep learning curve.
So I told Andrea, she probably still won't like this when we get there, but the biggest complaint I hear when a successor is really ready is, “Why am I paying them to come in and do nothing?” And I say, “That's exactly what I want you to feel like, Andrea — you're paying me to do absolutely nothing,” because that means Andrea has the confidence that she knows what she needs to know, and I'm not needed anymore. And that takes a long time to get to.
Different Configurations of Business Transitions
Elizabeth Ledoux: So I'd say five to ten years is a good runway, depending on where you are, and probably no closer than three or four years out would be a good time to start.
Andrea Carpenter: We've seen so many different configurations of this, because everyone has a different idea of how they want to do it. There's the owner with a management team of two or three people considering coming in. There's the person-to-person transition, kind of like Elizabeth and I are. There's the family situation, where you're talking about one kid who works in the business and one who doesn't, and another who's interested. Then you're trying to take care of everyone and all of those needs — who wants what, how you deal with fairness and equality, taking care of people and communicating with everyone about what's going on, without making anyone feel rushed or forced into something they weren't ready for.
Obviously, sometimes transitions are triggered by sad events — things we weren't expecting — and that can speed up some of the technical pieces. You can grab a copy of Elizabeth's book at beforebuysell.com. We called it Before Buy Sell because there are a hundred bazillion things you need to discuss before you ever get to the point of inking anything on paper. Depending on how many people you have and how aligned you are, some of the readiness Elizabeth talked about — it's easy for a successor to say, “I'm ready to take this over.” But have you actually demonstrated that, not just to yourself, but to your team, your clients, your transitioner? Do they trust you, especially if they're going to carry a note, or depending on how you're financing it? Have you talked to your spouse about your risk tolerance for taking a loan or putting your house up as collateral? There are so many pieces that surface as you get into this, and that's why the timeline extends out.
Elizabeth Ledoux: It's just very long. And on the flip side, for the transitioner — are you really ready? Are you ready to have somebody come in, help them, and watch them take over? Are you ready to let go? Are you ready to move into a totally different role? Because almost always, to support two people at that ownership level when the business has only been supporting one, the business needs to grow — and hopefully your successor is really interested in driving that growth with you.
That's a really interesting feeling of being ready, and then figuring out what you're going to do with the extra time. You really need to be moving toward something you want to do. Otherwise, you're going to stay in that business, your successor is going to be looking at you trying to get you to move out of your seat, and you're going to say, “Well, I don't have anything else to do, I'm pretty happy here.” And the successor is going to get unhappy, and that's where a lot of conflict starts — when the transitioner isn't moving toward something else they want more.
The Two Biggest Mistakes in Family Business Transitions
Mark Graban: You've touched on some different risks and mistakes. Is there a most common mistake you see a family-owned business making in the transition, whether to the next generation or to an outside buyer? Are those different situations with different common mistakes?
Elizabeth Ledoux: I'd say if you're talking about a family business — where the assets, whether active operating companies or investments, are being run by generation one, and generation two is coming in to take them over — there are two big mistakes. One is not starting early enough. Two is not including the successors in the design of the transition. Those two things, I think, are the biggest mistakes.
Designing a Transition: The Four Ws
Mark Graban: Tell us more — when you say “the design of the transition,” other than timeframe, what does that refer to?
Elizabeth Ledoux: When you design a transition, there are many “whens.” We have a tool called the Transition Compass, and I like starting with the four Ws, the first being why. Why are we doing this in the first place? What are we trying to accomplish collectively, successor and transitioner, which is the inclusive part. What do you have — what are you going to transition, what are you going to keep? And then who it's going to go to, which involves inclusion or exclusion, because there is exclusion in a business, hopefully not too much in a family. So you have to navigate that inclusion-exclusion situation.
Then there are the many whens. If you imagine a timeline that could be three to ten or more years — fifteen, depending on how old the person is — there's a choice of transitioning while you're alive or not. If you imagine this timeline, there are things the successor needs to know they must commit to and learn, and things the transitioner needs to teach and get out of the way for. When am I going to get out of some of my roles? When and how am I going to transition the governance — the decision-making, like whether we're going to borrow a million dollars, expand into another state, or launch a new product — who decides that? And then there's the ownership piece, the many whens of ownership.
All of these things go into a design where they need to mesh together, and your successor has to be able to make a commitment. People don't live up to our expectations — they live up to their commitments. If you can't be clear with your successor so they can make a commitment to you, to do something, to learn something, to take something on, and you make a commitment back to help them do it, that agreement doesn't go well. They don't know what they're supposed to do, they don't do it, and I, as the transitioner, start judging — I lose trust, I believe they're not capable, because they're not showing me, but we haven't had the conversation and they haven't been able to make the commitment. So the design is in that communication, that relationship, and designing how it's going to go.
Mark Graban: Mm-hmm.
Elizabeth Ledoux: Which is why Andrea likes to plan.
Andrea Carpenter: I just wanted to add — sometimes people go through that process and one side decides it's not the right fit. But then you've already established, as an owner of the business, what's important to you, your non-negotiables, how you want to take care of people, what you need to live your next adventure. Then it's really easy to say, “Okay, is there another buyer out there? Do I want to find someone to buy the business directly? Do I need to go to investment banks? Do I want to look at private equity? Is a merger or acquisition something that might be appropriate here?” So even if going down the path of thinking about one option means that exact thing doesn't work out, again — it's a journey, not an event. You've already laid the groundwork, set the direction, and that gives you so many more options later if the situation changes. That's such a big gift for yourself and your family.
Navigating Family Conflict Over Inheritance and Control
Mark Graban: This seems like a big theme of a lot of popular TV shows. How often do you run across family conflict or drama about inheritance shares of a business, or who gets to control it? Or does that tend to work itself out by the time you're involved?
Elizabeth Ledoux: The best way to navigate that is to get in front of it and not try to clean it up once it happens. Usually there are some challenging conversations that need to happen while you're designing the whole thing, and that's why it's important to have a facilitated conversation — so somebody can bring you together and help you see that sometimes you're saying the same thing, just differently, or help you find that tiny nugget where you can come together. Nobody gets everything they want in a transition.
In all my years, we've used something called the objectives matrix, where everybody writes down all their objectives, we put them together, and create a collective “why.” Why are we doing this? What are we trying to achieve in our lives, for the business, for our employees, for our individual families and for the greater family if it's a family business? Nobody gets everything they want, but your goal is to get a majority of the most important things, and to help people actually understand what those important things are.
So there's always a challenging conversation to have. The hope is it stays a conversation you can have, and doesn't turn into a situation where you're opposed or angry — because once those feelings start, you're unpacking and repairing instead of getting ahead of it. That's where the iMap comes back in — “Hey, you'd be a better CEO than I would.” “And I really don't want it.” Then parents are sitting there thinking, “How are we going to decide between our son and daughter?” Well, you're not going to be the ones living it — why don't we let them decide, let them design how they want to work together, instead of us dictating or worrying about it?
Andrea Carpenter: The last thing I'd add, adjacent to the conflict idea — I hear this theme a lot, people worried about their kids being entitled. Certainly there is some entitlement, but I've talked with so many successors, and as a general rule, they're just trying to figure out what it means for their life. The questions they ask are really them being curious, trying to figure out how it's going to impact them and their family, and the time expected from them, and whether it aligns with what they want. That can get misconstrued easily — when people start asking questions or poking into uncomfortable things, it gets read as, “Well, you just think you deserve this.” That can become another source of family conflict.
Certainly there are people who are entitled, which isn't great. But as a general rule, most successors I meet genuinely want to be good stewards, if it aligns with their family's vision of what that looks like. It's a cool place, and also a hard place, to be as a successor.
Elizabeth Ledoux: In an unfacilitated conversation, that curiosity — sometimes I tell families, “Well, my son is so, has so much energy and wants to get in right now,” and I say, “You are so lucky to have somebody who's interested at all, who has a vision for the future of the family and stewarding the money or the business. It's such a lucky thing to have.” But it's easy to misunderstand, from a parent's perspective, that curiosity and push as something you want to manage and handle, versus reading it as entitlement — because it's often seen as greedy, “let me get my hands on this now so I can go do what I want.” And like Andrea said, that's not usually the case.
Succession as an Identity Question
Mark Graban: Andrea, back to your bio — tell us what it means to be “identity first” when thinking about a business, whether you're an owner or a successor.
Andrea Carpenter: I think it ties nicely into the people, and who they are at their core. When you invite each person to the table to share who they are as a person — we talked about the iMap, about wiring, about objectives, what's important to each person, different timelines, different expectations, the people they surround themselves with — all of that forms their identity, the way they show up in the world. When you can honor all the ways everyone involved in a transition is going to show up, that's the best way to design a future that's going to work for everyone. That's how you get that win-win-win: a win for the owner, a win for the successors, and a win for the business, for your community, that your business or your IP lives on to another day to keep helping more people, to keep spreading the good in the world. That's what it means for me.
Helping Owners Find Their Next Adventure
Mark Graban: I imagine there might be another dimension where somebody identifies so strongly with their business that they wonder — how much of this transition coaching is about helping someone figure out whether they can actually enjoy retirement and manage that transition, or is that for somebody else to help the owner with?
Elizabeth Ledoux: I'd say helping them discover that goes back to the objectives matrix, the compass, and the many whens of when they're going to let go of things. We absolutely help them see a next adventure, and it's not walking off a cliff — that's pretty rough. When you walk off the cliff, you're on your own, and you're either going to sink or, hopefully, fly.
The way I like to see it is that the owner is going down a highway at a certain speed, and the successor gets on the on-ramp, speeds up, and comes alongside, going down the highway together at the same speed. Then pretty soon that successor starts going a little faster than you as the transitioner, and pretty soon, as they speed ahead, you get off on the off-ramp. It's this beautiful journey instead of walking off a cliff. There are so many people I've personally coached who went out, didn't do the work, went to an M&A firm, sold their company, even worked for the acquirer under an employment agreement for two or three years, and hated it. Then they're sitting in their office at home with no staff, nobody around them, no real purpose for getting out of bed, and they get depressed and unhappy. They come to us sometimes and say, “I'm so unhappy, I'm going to start a new company,” but they don't have the energy and don't want to do it again.
So then we help them find a next adventure. But it's so much easier to find that next adventure within the journey, because as your successor comes in, you have the opportunity, over a few years, to figure out what it's like not to work as hard as you have in the past, and to take the time to understand what you like, what you want, to get to know your spouse a little better, get to know your kids again, be with grandkids you haven't had time for. There's a lot to discover on the transitioner side.
Andrea Carpenter: The statistic is that 70 percent of people will regret selling their business. We haven't run a study on what the statistic is for people who successfully pass it to a transitioner and get to see it live on — maybe we should. You've been more intentional about the way that looks. About 50 percent of the people who reach out to us to inquire are the successor, because they feel their transitioner isn't moving — and that's a lack of a defined next adventure or path forward for them. That's a vulnerable, scary feeling to think about. So giving yourself the gift of time to really design that and figure it out is a gift not just to yourself, but to your family and everyone around you.
Closing
Mark Graban: Maybe there's someone you have in mind for a future episode — someone who might want to talk about their mistake of selling their business.
Elizabeth Ledoux: I have a great one. I have a few, actually.
Mark Graban: Well, let's follow up about that — maybe coming later this year. Really appreciate you both being here. Again, from The Transition Strategists, Andrea Carpenter and Elizabeth Ledoux. Check out the show notes for a link to their website and a link to the book. As we've heard during the episode, Elizabeth co-authored It's a Journey: The Must-Have Roadmap to Successful Succession Planning.
Thank you for sharing your favorite mistake. Andrea, I'm glad it sounds like everything worked out — you decided to go back for child number two. I wish you the best there, and wish the both of you continued partnership in your succession journey. Thanks for being here.
Elizabeth Ledoux: Thank you.