Planning Without Leaving: Why a Transition Strategy Is a Multiplier, Not a Countdown

What if the reason you keep pushing “start transition planning” down your to-do list has nothing to do with being busy? 

In this episode, Elizabeth Ledoux speaks to the owners who are still building. Not winding down, not stepping back, still fully in it. For these owners, the phrase transition planning often lands like an ending: a date, a handoff, a last day. Elizabeth calls this the countdown myth, and it keeps successful owners stuck in a quiet trap where the business runs through them and planning starts to feel like the only thing left is goodbye. 

Then she flips it. A transition strategy is not a countdown. It’s a multiplier. It multiplies your clarity, your options, your people’s trust, and your own bandwidth. Elizabeth shares her own story of building her strategy five years ago, long before she knew who her successor would be, and how that work led to a new business partner and a company that’s now multiplying. 

Key takeaways from the episode: 

• The clock is already running. Avoiding a strategy doesn’t keep the clock off; the business is aging, your people are waiting, and the market keeps shifting. 

• The more successful you are, the more the business runs through you, even if you’ve stepped back from the day to day. That dependence is the quiet trap. 

• You can fully plan and stay another decade or two. A strategy is a direction, not a departure date. 

• A strategy is only intention on paper. The real value is in the planning process itself, the deep reflection on what you want and how you want your people treated. 

• Starting early puts the odds in your favor. No plan means choosing from whatever’s left when the day comes. 

• Blend your transition strategy into your business strategy. The business moves, and you start moving with it. 

• Roughly two thirds of businesses fail in transition. The ones that succeed treat time as an asset, not a threat. 

Chapters in this Episode:
01:00 – The line on your to-do list you keep moving
03:00 – Who this episode is for: still building visionaries
04:15 – The countdown myth and why the word exit resonated poorly
06:00 – Next adventure thinking instead of an ending
07:45 – The countdown mindset: trying to keep the clock off
09:15 – The quiet trap: when the business runs through you
11:15 – Planning from fear vs. planning from strength
12:45 – The multiplier reframe
14:15 – Elizabeth’s story: building her strategy five years early
16:15 – A strategy is only intention on paper
18:45 – The planning process and the deep reflection
20:45 – Leveraging time and putting the odds in your favor
22:45 – Coming from positivity, not fear
24:15 – Staying relevant, staying of value
25:45 – What it looks like in practice: name a direction, not a departure
28:15 – Time as an asset: the rear admiral’s lesson on pivoting
30:00 – Where to go from here: a few days of reflection

Connect with Elizabeth Ledoux and the Transition Strategists:
Website: https://transitionstrategists.com/
Facebook: https://www.facebook.com/thetransitionstrategists
Elizabeth on LinkedIn: https://www.linkedin.com/in/elizabethledoux/
Transition Strategists on LinkedIn: https://www.linkedin.com/company/transitionstrategists/
Transition Strategists on YouTube: https://www.youtube.com/@transitionstrategists

Subscribe to “The Business Transition Roadmap with Elizabeth Ledoux” on your favorite podcast player:
Spotify: https://spoti.fi/3MxSYA2
Apple Podcasts: https://apple.co/3IhMMux

Our Sister Show: Your Next Gen Friend
Hosted by Andrea Carpenter, Your Next Gen Friend is for the next generation stepping into leadership in family and private businesses. If you’re a successor figuring out your path, this show is for you.

Website: https://yournextgenfriend.com/
Instagram: https://www.instagram.com/yournextgenfriend/
YouTube: https://www.youtube.com/@yournextgenfriend
Andrea on LinkedIn: https://www.linkedin.com/in/andreakcarpenter/
Spotify: https://yournextgenfriend.com/open-spotify
Apple Podcasts: https://yournextgenfriend.com/apple-podcast

Get Elizabeth Ledoux and Laura Chiesman’s latest book, “It’s A Journey: The MUST-HAVE Roadmap to Successful Succession Planning”: https://amzn.to/3oq2LQv

Planning Without Leaving: Why a Transition Strategy Is a Multiplier, Not a Countdown Transcript

Elizabeth Ledoux:

Somewhere on your to-do list, there’s a line that says something like, start transition planning. And it’s been there for a while. Not because you forgot about it, but because every time you look at it, it feels like it’s asking you to do something or admit something that you’re not really ready to admit.

So you move it, you move it to next quarter, to after this launch, after this hire, or after this busy season. And it sits there quietly doing nothing. And time keeps moving. You don’t really realize it, but there’s a cost, and there’s a cost that is more than you may realize.

That’s what today’s episode is about. It’s not about the plan itself, but it’s about the story that you may have been telling yourself about what making a transition plan or a transition strategy actually means.

Welcome back to the Business Transition Roadmap. I’m Elizabeth and this one actually is for the owners that I think of as still building visionaries. So that’s how I label them. They’re still building visionaries. you’re not winding down yet, you’re not

Getting out, you’re still in it, you’re still growing, and you’re still the reason that a lot of it works, which exactly why this episode is for you. So today what we’re going to talk about is planning without leaving. And this is where we’re headed. So the countdown myth.

When owners hear transition planning, they actually picture an ending. And I’ve been doing this for over 30 years. About 30 years ago, I started into what was called exit planning back then. And I cannot tell you how the word exit resonated poorly with business owners. If I would walk into a room and I would say, Hey, guess what I’m doing? I’m doing exit planning, they would be just

Just like, man, I do not want to talk to you. I am not ready to exit. I am nowhere near ready to exit. So yeah, this conversation is not for me. And I started working on the concept of maybe a next adventure and what a next adventure might look like. So instead of an exit, which is kind of an ending or a final thing in people’s minds.

I started thinking about what would a next adventure look like? And if you think about decade thinking, is a next adventure something that is potentially in your mind? You know, I think we’re always

Wondering what’s next and what would be fun. And maybe staying in the business would be fun. Maybe staying in the business for a while, maybe a long time. maybe staying in it and not working as much, that would be fun, or maybe actually exiting at some point in time, leaving, and we all know.

Going to exit our businesses one way or another, right? Vertically or horizontally. So, you know, how do we do it and how do we do it well? So, again, when most owners hear transition planning, they picture an ending like a date, it’s on a date, it’s a handoff, it’s the last day, and that picture is the whole problem.

So if you think about the mindset of maybe like a countdown mindset. So the day I plan is the day the clock starts on me being gone. So I want to avoid planning so I can keep the clock off. I don’t want that clock to start.

But in reality, the clock’s already running because time is moving. It’s moving every single second, every single day. Your business is aging, your people, they’re you know, they’re waiting, they’re they’re moving, but they’re waiting to figure out what’s going on. the market is shifting, and you know what? You are getting older also. So this

idea of keeping the clock off or not needing to deal with it now or you know the mindset of gee I’m just too busy, that’s a quiet trap. So the more successful you are typically the more the business runs through you and it might not you might not be doing all of the day to day stuff anymore. But if you think about you know

Gosh, just the financing or the relationships or some of the some of the power that you have, the knowledge, that crystallized knowledge that sits there, that you just know how to run this business. the business really does run through you, even if you’re not doing a lot of the day-to-day. And when that happens in this quiet trap, and you and the business is dependent on you.

The more that planning starts to feel like the only thing left is goodbye. So, you know, I have to run up to the end of it and then I’m gonna have this cliff. It’s gonna be goodbye and I will know.

In my expertise and my experience, that is it is a trap because people aren’t ready and things just don’t come together. So what what we’ve tied together here is that planning means leaving.

And what I know is you can fully plan and actually stay another decade or two decades. So this countdown kind of planning is from fear. But what we think of as kind of multiplier planning, right, that comes from a place of strength. So I like to

Invite you to think of planning. when you think of transition planning, it’s not exit planning, it is transition planning, it is next adventure planning, and it’s not just next adventure planning for you, it’s next adventure planning for everybody that depends on this business, including your family, even if they’re not working in it at this time. So let’s reframe this that

Doing your transition plan is not the beginning of an end. It’s what lets you keep building without carrying all of it alone.

So I’d like to talk a little bit about this multiplier reframe. And when you when you walk into and you start to imagine and expand your mind into what is possible with this business over maybe the next decade or two decades or three or more, if it’s gonna be a multi-generational business.

That’s a pretty cool thing because as we age, you know, our runway starts to get shorter and our mind sees, you know, instead of being 40 and having another, gosh, 20 or 30 years to enjoy and work in the business and make decisions and be that entrepreneur. As you age, you at 60 may only see 10 years. You may only see another decade if you see that.

And as we do that, our minds narrow because you know it’s what is possible, but you frame that inside of what’s possible for me. you can reframe.

your timing into something that’s much greater into a multiplier and I actually was able to do that when I did my strategy years ago it’s been about five years now I was nowhere near leaving I did not know who my successor was and all I knew is that I was getting to a point in time that I needed to start thinking about it. So and this is just my story

So I started doing that. And now I’m on this road to have my next adventure, but I also have my new successor who’s my new business partner. And because of the work that I did five years ago, we are multiplying this company and I’m playing with ideas and thoughts that’ll go many decades likely after I’m gone.

So this multiplier reframe really allows you to expand your thinking and not just you know work in a in a runway that’s maybe five or ten years, that’s what you think and what you see and what you have left, but to bring in some new energy and some new people in order to multiply your strategy. So right now in

many of the in many of our clients when they come in, the decision making capacity runs through them. It just it you know you’re you’re the entrepreneur, you’ve been making all the decisions, and even if you delegated some of the decisions, likely many of those are more day-to-day decisions, not investment decisions, not how much money will I keep in the business, where will I get it if I need it, not financing

and maybe even not you know not decisions that are more strategic. So when you look at this multiplier reframe, you can

Imagine that you’ve got the opportunity to create a strategy where not only you know what you want and maybe how long your runway is. and by the way, a strategy is only intention on paper. I cannot tell you how many times we, including me in my plan,

You put it on paper, gives you clarity, and it’s the process of planning that is actually the most important part because I don’t know about you, but basically every plan I’ve made, including small ones, even as small as for a dinner party, they don’t go as planned. something always comes up in a dinner party situation. Somebody’s late, somebody’s early.

Yeah, whatever you’re making doesn’t come out exactly the way that you think that it will. And that’s just a really tiny example. So imagine that you’re looking at an entire transition strategy that’s gonna go over many, many years. It is not gonna go as you plan.

There is no possible way. So the purpose of the planning, the purpose of creating the strategy in the first place is to create awareness and to do that deep reflection and that deep dive into what do I really want? And how do I want to live my life? And how do I want

When I can’t do it anymore, because I you know, if you want to run it all the way up to the end, that’s fine. you may not be here, but when you either can’t or don’t want to do it anymore, how do I want these people to be treated? how do I want the culture in my business? How do I want all that to happen? So

So this the planning process is really about the deep reflection. And I think that’s where this multiplier reframe comes because as soon as you stop fearing the exit or believing that it’s too far away,

Then you can come from a different perspective and come from a place of positivity, not fear, where you can look at it and go, Wow, of course, I can live the life that I want to, I can leave the business as I choose to. I can

Leave over many, many years, or I may find that it’s better for me to do a you know, an actual sale to a third party, wash my hands of it, and move on to a next adventure that I’m really excited about. So there’s multiplier reframe. Just want to invite you to reflect for a moment. Are you

Avoiding the concept of transition strategy work because of fear, or because you’re just too busy, or are you sitting in this powerful position where you’re thinking, man, every decision I make right now is going to be a decision that is actually going to help me help my company.

Help my successor, if you know who that is, or prepare the business for a successor, but it’s gonna help us to do more. It’s gonna help us to gain value and it’s gonna help us to move into a safer place just in case something happens to me. So

If you think about these this strategy, when you start a strategy early, you create or have a multiplied amount of options. So no plan, if you do no plan, it means choosing from whatever’s left.

or whatever happens on the day or the time frame that you decide that you’re not going to be able to run the business anymore or you don’t want to. If you have a strategy, what it does is it makes time your friend. You can it people say, well, it buys you time. Well, you can’t really buy time. But

you can leverage time. You can use time to your advantage. And my wonderful mentor in my life, Dr. Tom Hill, out of St. Louis, Missouri, he used to he taught me OIMF.

Odds in my favor. Well, I will tell you that when you have a strategy, you put the odds in your favor that you are going to achieve what you want to achieve as you navigate out. I will tell you that doing transition work is not easy.

It is a big, deep, reflective time, and you have a choice of deciding whether you want to make it a negative or a positive. So the negative would be like, my gosh, I’m getting so old. I have to do my transition strategy work because I might get sick or I might something might happen, or and I just have to protect these people. So that’s all coming from

kind of a negative place. And when you come from that perspective, it is, I think, it is something that is nobody wants to do that. Nobody wants to go, wow, let me look at, you know, my mortality. Let me look at not being able to work in this business. I like to flip that on its head and come from a very, very, very positive mindset.

What’s possible? If you can leverage time and you can make time your friend in a strategy, you can walk into transition, strategic transition work and come from a very positive place.

I am so excited about my next adventure. I’m so excited about helping others grow and develop. I’m so excited about building this company. Let’s say you want to stay for many, many decades until you can’t even go to the office anymore. You can’t walk, can’t go to the office, that’s fine.

I want to design this business so that I can be me, I can do what I want to do, I can stay in as long as I want to, or I’m able to, and I’m relevant, I’m of value, I’m doing what I love. Being relevant, being of value, I think is one of the

And one of the things that we fear, you know, gee, it’s great, Dad, you’re always here, but you know, you really are a bother. You really are not productive with us and you’re really derailing the business all the time. Those are things that we hear pretty often. And I think about that and and I’m like

with some communication, with some strategic work, with a plan in place, those things don’t have to happen. So

Encouraging you as you start to think about this, that transition strategy work is not easy work. There are a lot of emotions in it, and especially if you start to bring in other people with you, maybe some successors or some people that are around you. could be a wife or a husband, a spouse. they may not be working in the business, but if you’re transitioning to family members, those spouses have a big, big, big investment in how the family.

works together and how it runs.

So, what does this look like in practice? For me, what it looks like in practice is that you name a direction. You you get a direction on where you want to go. And it’s a transition direction. It’s not an actual departure, it’s not an exit date.

It’s not a fun a final thing in your life or a final number unless you choose for it to be so, which is fine. I think it’s fine to do that after you’ve done some strategic work and actually understand how how an exit, a true exit, a sale to a third party.

Will impact your life financially and also emotionally through relevance. there’s so many business owners, and again, if you’re here that you might have in your mind, there’s so many who go, gee, I’m tired, I’m gonna sell, and then what happens is about three months later, they are bored, they don’t know what to do, and it’s a huge uphill battle to go start a new thing. they actually get depressed. So

In this work, in transition strategy work, I encourage you to think about at least five years, if not ten. You could go out as long as fifteen or twenty. you name a direction, not a departure. then what you do is you

Some conversations along the way because if you have a if you have a strategy and I think in timelines, so if you have a strategy.

You can have milestones where it’s kind of like, hey, I’m just gonna run this business like it is for the next three or four years. I’m going to start to make these decisions inside of the business. I am going to start to whatever, pay off debt, whatever those strategic things are that get you to a place in a few years where you can start to then make another step. Maybe that next step is to in the three years you watch your people.

People

and you mentor them a little bit in a different way, and you test the waters and see if they’re able and if they’re willing and if they’re willing to put in the time and what their risk tolerance is to get to the end of those three years, then you start to maybe have some more conversations with them. That could be what it looks like in practice. So you’re not going to

You’re going to start to

Look at your strategy, and you’re gonna sort of blend it into your business strategy. So the business moves, but you start moving also. Instead of staying in the same place where you are today, you start morphing a little bit and you start thinking about what it would be like to be out of the business a little bit. So my point is is that

This is not a wasted effort. It’s not a here’s my business strategy and here’s my transition strategy, and they’re totally separate. And I’m gonna keep working on my business strategy and hold off on my transition strategy because it might be a wasted effort. I will guarantee you it is not a wasted effort. If you treat time as an asset and not as a threat.

The best outcomes almost always go to the owners who start early. While while they still have options and they still have some leverage, the ones that we see fail, and this is my belief, and you’ve heard it here on this podcast before, the businesses that fail, and remember, statistically, about two-thirds of them fail in transition, those businesses, I believe, are the ones that.

don’t use time to their advantage and they don’t put the odds in their favor and they don’t keep the open options. I had the opportunity on an earlier podcast just a few weeks ago to have a rear admiral with me and we were talking about planning and I could only imagine how much planning goes into and I kind of know because my son is

An F-18 pilot in the Navy. and you know, I listened to him, my son.

And all of the work they do before going to fly a mission. And then I hear the de you know how much time they take after the debrief, or after the mission for the debrief. so I’m talking to Mike Wettlaufer the rear admiral, on my podcast, and he said, he said, you know, he said it is not again about the plan. It’s about the planning process. It’s about taking the time to do that. So

He said what it does is it allows a team of people and it allows the leader to pivot when they need to pivot. Because remember no plan is gonna go as you as you plan it. never happens.

The what’s gonna happen is you’re gonna go through a strategy, you’re gonna go through the planning process, you’re gonna take the time to do that, you’re gonna reflect on it, and then you’re gonna be ready. You’re gonna be ready to grow your business with your business strategy integrated with your transition strategy, and you’re gonna be ready to pivot when it needs to happen. You also are gonna have people around.

you who are ready to pivot with you. You’re not going to be by yourself. And so some of that weight that you carry, especially as you get older, you know, gosh, I haven’t done anything. And you know, I’m really not ready to exit. I’m really not ready to leave. And I’m afraid to tell anybody. But you know, I hate to break it to you. People realize that you’re getting older. It’s not hard to see. And we all are doing it. So

Where do we go from here? What I’d like to encourage you to do is to maybe over the next few days take some time to consider what you’re doing in your business, how you’re living your life, what you would like to have as

I don’t know, you could call it a legacy, but what would you like to leave? How would you like to leave these people, this business, this community that you’ve nurtured and grown for so long? And just do a little bit of thinking around that. And then start to consider how you might leave them.

And what might that take? That’s the strategy that you want to build because as you build it, it will take many years for them for you to leave them well. It’ll take many, many years if you do it right. And so I’d like to encourage you to take that time over the next few days, just reflect, do a little bit of journaling, and consider whether.

your plan is actually you leaving or if your plan is just a continued journey that you’re on to continue to build this business well and continue to allow it to go forward without you at some point in time.

Planning is not a countdown. It’s a multiplier. It’s a multiplier on your clarity for your decisions. It’s a multiplier on your options available to you and how it allows you to pivot. it increases your people’s trust, so it’s a multiplier there. And it’s also a multiplier in your own bandwidth. Because instead of trying to continue to do it the way you’ve done it, you can morph and shift over time. Again, creating the option for you to stay for many, many.

decades if you’d like to. I believe that you lose nothing, except maybe a little time, but usually it’s well spent time. I think you lose nothing by having a great strategy. I think it makes your business stronger and I think it helps you to envision what’s next and gain great, great clarity on that. So I’d like to invite you to shift your thinking. If that

Line is on your to-do list, start strategic transition planning. If it’s on that to-do list, then because you’re not ready to exit, you’re pushing it down the road. I’d like to invite you to engage in it, embrace it, and start to think of it as a multiplier for you to live the life you want to live and help others do more in their lives as well. So thanks for joining me and I will see you next time.

SCHEDULE A COMPLIMENTARY CONSULTATION

The Business Transition Roadmap with Elizabeth Ledoux

How do communities thrive? When businesses experience healthy growth and transition. Join CEO of The Transition Strategists, Elizabeth Ledoux as she and her guests identify what makes a successful business transition roadmap. If you know you want to transition or exit your business “one day”, today is the right day to start planning. This show will give you the roadmap.

If you’ve enjoyed this podcast, you can check out other episodes here: Podcasts – The Transition Strategists