Facing Fear: Why Staying Stuck Costs More Than Moving Forward

What if the biggest obstacle in your transition isn’t strategy—it’s fear? 

In this episode, Elizabeth Ledoux unpacks the fears that hold founders and successors in place, even when they say they want forward movement. She explains how hidden fears shape decisions, limit communication, and keep people isolated at the exact moment they need connection the most. 

Through real client examples, Elizabeth explores why transitions trigger identity questions, financial worries, concerns about relevance, and a desire to keep “skeletons in the closet.” She offers mindset shifts and practical insight for naming fear, understanding it, and moving through it with clarity and bravery. 

In this episode: 

• The fears that keep entrepreneurs and successors stuck 

• Fear of loss, fear of relevance, fear of conflict, fear of regret 

• Why isolation amplifies fear—and connection shrinks it 

• The cost of staying stuck: missed opportunities, silent resentment, delayed decisions 

• Shifting from the “gap” to the “gain” 

• Why bravery is less about bold action and more about letting someone in 

• How transparency, shared vision, and conversation unlock momentum 

• The role of the Evolve program and immersion work in breaking fear-driven patterns 

Chapters in this episode:

00:00 — Welcome & Why Fear Matters 
01:12 — The Universal Reality: Everyone Has Fear 
03:10 — When Fear Quietly Rules Your Decisions 
04:55 — The Most Common Fears in Transition 
08:20 — Fear of Loss: Identity, Control, Passion 
11:04 — Fear of Not Being Good Enough 
13:18 — Fear of Conflict & Relationship Risk 
16:02 — Fear of Regret: Too Soon or Too Late 
17:45 — The Cost of Staying Stuck 
19:40 — How Isolation Amplifies Fear 
22:20 — Skeletons in the Closet: Real Client Stories 
27:10 — Shifting from Gap Thinking to Gain Thinking 
30:03 — Bravery as Letting Someone In 
32:40 — Building Shared Vision Through the Evolve Program 
35:22 — Final Invitation: Look at Your Fear, Move Forward 

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 

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Check out “Your Next Gen Friend Podcast” with Andrea Carpenter 

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

Facing Fear: Why Staying Stuck Costs More Than Moving Forward Transcript

Elizabeth Ledoux: 

Hi everyone and welcome back to the Business Transition Roadmap. I’m Elizabeth Ledoux and I’m so excited to be here with you today. The focus of our topic today is on fear. I’ve been doing some thinking about fear and a little bit of research about fear. And I’ve also been working with quite a few clients lately and just watching

what’s happening in these clients’ lives and what’s keeping them from coming together, what’s keeping them from moving forward, and what’s keeping them, in essence, stuck or staying. They may not even seem or feel like they’re stuck, but just what’s keeping them where they are today, where they’re unwilling to move forward. So if you’re a business owner or you’re a successor who

is considering going through a transition, whether it’s coming into the business as a successor or ⁓ as an owner founder leaving the business, I invite you today to just, we’re gonna reflect a little bit on our fears and do a little bit of a deep dive into that. So what I see with regard to fear is ⁓ one, we all have it.

We all have fear. get up every day and we have fear of maybe something happening or something that we’re worried about. Fear is interesting. It can be very, very real. It also can be something that we just create in our own minds, something that maybe has happened to us in the past that we’re worried will happen to us again and we’re seeing some of the same patterns coming together. Or it could even be

something that we’re about ready to do that we’ve never done before and the future looks a little unclear or little murky. So a thought is that maybe you’re not staying in this position or stuck because you lack a strategy ⁓ because you may have something in your head or something in your heart that you go well it probably would work ⁓ that strategy but potentially it’s because of fear and

One thing that happens though is if we can understand our fears and if we can look at our mindsets, which are our beliefs or our feelings about what is true or what could be true, then what we’re able to do is move forward ⁓ with clarity and with confidence and we’re able to see what might happen to us in the future a little bit more clearly. So.

When you look at this, ⁓ whether you’re a founder or a next generation leader or thinking about transitioning, ⁓ typically this transition stirs up fear. And one of the things that we found or a belief that I have is that if you don’t face the fear, if you don’t face this challenge, then basically it kind of rules you. It’ll be a…

barrier that you will have and you’ll know it’s there. And every time you try to take a move or make ⁓ a forward movement with your transition, there’ll be something in your heart or something in your head that goes, ooh, ooh, ooh, I don’t really want to go there.

So when you think about transition, some of the most common ones we hear, and I’m sure you’ve thought of them also, is just like, hey, I don’t know what I’m going to do when I get done with this business. I don’t know how I will be fulfilled. ⁓ I don’t know how ⁓ I’ll make money. So maybe I will or I won’t have enough money to live the life that I want. ⁓ Maybe there’s a fear of not being able to take care of people.

Some of the most common ones and some of the hidden fears that we see is a fear of loss. So if you’re like, I don’t know what I’m gonna do when I get done with this business and I’m not sure I’ll be fulfilled, go deeper than that. What’s underlying that? So is there a fear of not having passion in your life, which would be a fear of loss of something?

Is there a fear that maybe you will lose some of your identity? Is there a fear that you’ll lose control? Is there a fear that you might not be relevant anymore in life and in the world just because you’re not a part of this business anymore? Is there a fear of another one? Is there a fear of maybe not being good enough?

So you’re not ready or willing to leave yet, even though you might have enough money in the bank to do it, or with a good sale of the business, good transaction, you would have enough. But is there a fear of maybe not being good enough if you’re comparing yourself? Because comparison is the thief of joy. So are you fearful that you might not be good enough that you’re gonna give up the opportunity to keep working and keep trying?

for that because we all have that imposter syndrome a little bit. There could be a big fear of conflict. And if you really name that conflict, what is that? Where is that conflict? And I’m going to give you some of my thoughts on my current clients. And that fear of conflict is present in all of them, in each and every one of them right now.

⁓ Then what about the fear of regret? So if we dive deeper into, I don’t know what I’m going to do when I get done, or I don’t know if the business is going to be okay, or I’m unsure if I’ll have the life and the money that I need. If you dive deeper, is it loss? Is it not being good enough? Is it conflict that might come about? Is it regret? The idea that you made the wrong move, you got out too soon. ⁓

Maybe it could even be that there’s some regret because you got out too late, just because you didn’t have a strategy in place to make it happen. So what’s the cost of staying stuck?

Procrastination, really interesting. We do it with estate planning. That is very, very common. ⁓ Sometimes we do it with buying insurance. Like, yeah, I’m healthy. I don’t need insurance right now. It’s OK. ⁓ We do it with business transition. And many times, we make delayed decisions. So we don’t want to paint the picture.

of what it looks like maybe 10 years ahead, especially if we’re a little bit older. And I did a different podcast a while back on the idea of tenure thinking because tenure thinking is very, very, very positive in an entrepreneur’s life. It’s unique that an entrepreneur can do that. Then it’s very positive to have a 10 year vision, a personal 10 year vision.

Not one just for your business, but one for you personally. So, but as we get older, it’s harder to say, hey, you know, I’m 65. I’m going to have a 10-year vision of 75. And my vision may or may not include how I’m currently working today. It likely won’t include if you’re going between 65 and 75. You may not want to be working in the same way. You might still be engaged in the business, however, or you may not. So,

When you paint that picture of what it looks like in your future and you’re thinking out maybe five years, 10 years, 15 years, then we have ⁓ sometimes delayed decisions. Sometimes it’s ⁓ like silent resentment between generations. Like, hey, when are you gonna leave so I can come in and take over? ⁓ Sometimes it’s a missed opportunity. So the cost of staying stuck and not moving forward.

and having this fear actually kind of control you or own you is that you might have a missed opportunity to prepare your successors. So thinking along those lines, what’s the cost there of keeping the control and keeping your role and keeping your position and not mentoring someone early enough so that they can grow and develop. And then there’s isolation.

So isolation because you’re trying to potentially make these decisions by yourself. That is also fear. ⁓ Not wanting to let somebody in to have a conversation. Why? ⁓ I’m going to give you some examples because I told you I would. ⁓ We have clients right now who

You know, they’ve been managing the business. They’ve been doing a good job. They’ve kept it in business for years. instead of knowing and seeing what they have done and the value that they’ve provided, what they’re doing is looking at their financials and looking at their decisions in the rear view mirror and saying, my gosh, you know, I don’t want anybody to know that I made that decision. I don’t want anybody to know.

that we lost money that year and we lost that much. I don’t want anybody to know that I’ve been paying for someone’s car or someone’s cell phone or some, that you’ve been paying somebody potentially for something that maybe you did out of your heart, but it may not have been like the best business decision. So we have all these business decisions that

⁓ It’d be nice if we could just keep those skeletons in the closet and just leave them there. It’s the perfect place for them because we don’t want anybody to know. And we’ve been able to keep those secrets and keep doing it our way for many, many years. So ⁓ the idea of isolation, because as you get further down the road, ⁓ isolation doesn’t work. You cannot go through a transition without having

at least two people. You’ve got to one transitioning and you’ve got to have another coming in and being your successor. And if the successor comes in with limited information, I know that you can imagine what it would be like. I mean, imagine, which is a true story, imagine what it would be like to be the son of a father. You’re willing to come in and work in the business. Your dad’s still there.

and he has such a tight rein on the financials of the business. Now, your CEO, right, your president of this company, you’re making the decisions and you’re running it all and making all of the decisions in a vacuum with no financial information. The only thing that this president CEO knows, the only thing that he knows is how much revenue. No idea on cost of goods sold.

No idea on gross margin. No idea on any of the expenses. Why? Because one, the owner may like control. That could be a fear, not wanting to let go of the money strings. But two, skeletons in the closet. A fear of somebody finding out and then somebody, a relationship outside of him

being shifted or changed because of inequality and lack of fairness. Now, all of those decisions, all that stuff is water under the bridge. It’s all done. It might be okay for you to hang on like that and hang on until you are no longer on the planet, until you’re gone. But by keeping those fears in place, it keeps you stuck.

in this example that I gave you and it’s a real story. So it keeps you stuck where you are. You live with that fear and anxiety, hoping nobody finds out until you’re gone. And then when you’re gone, it’s like, well, it won’t be my problem. However, if you are an entrepreneur that likes to put people first, you really kind of have an obligation.

And maybe it might be healthy for you and for others for you to kind of unpack some of those skeletons in the closet and unpack some of these things that are in your heart and your mind and start to really engage and be brave ⁓ to address some of this stuff. Because what it takes to face this stuff, it does take bravery. So first thing it takes though is a mindset shift. So instead of like, ⁓ you know, I

made a whole bunch of decisions in my past and they weren’t very good and I don’t really want anybody to see them versus ⁓ I made decisions in my past with the best information that I had available to me at the time and I did what I thought was right and what I thought would be best for the company and best for the people and best for our relationships and best for our customers and our clients. I’m proud.

of a business that’s here today. That’s a simple mindset shift. instead of focusing on, talked about this in earlier podcasts too, instead of focusing on the gap, what you’ve done that hasn’t been good, what you have not achieved, whether you’re good enough or not, you’re focusing on the gain. We have a business that exists, we have a business that’s profitable, we have a business that’s in place, we have a business that cares about people, we have a good culture.

We provide great services ⁓ and we’ve got a strong, strong business. And by the way, as the owner founder, you’re the leader of that. Good job. So shifting that mindset, how do we move from living in the gap to living in the gain? What does that look like? And the tools, ⁓ it’s really like if you talk about bravery, it’s about not just a bold.

like action of bravery, but it’s about being brave enough to let somebody in, to let somebody in to see. ⁓

your challenges, to see your faults, to see your weaknesses, ⁓ to see what you’ve done well, to see what you haven’t done well, to see the lessons learned, right? The lessons learned, they don’t always come from the best times. They typically, typically come from our struggles. And those struggles are what we need to share with our successors, because that’s the meat. That’s the good stuff that’s really gonna help them.

get through their hard times as they encounter them along the way. So bravery, bravery to listen, bravery to share. Thinking, what about, yeah, thinking, ⁓ emotional awareness, how you’re showing up. Just confidence is a way to tackle some of this stuff. ⁓ Conviction, maybe anchoring in what really matters most.

If these relationships and these people and this business and how it serves the community really matters most, making this bigger than you, bigger than yourself, your conviction to have this thing go forward without you, why? Because it’s bigger than you. You’re just that servant that’s gonna be making it all happen. And you’re the one that really led the way all the way.

until you actually transition out. And then focus. what it focusing, you know, what are you focused on? Are you focused on fear of transitioning and fear of what you might run into or are you focused on tackling the issues and making it happen? So I told you I’d tell you about a couple of clients. Currently have a few different clients that are in the beginning stages of their transition roadmap.

And so their transition roadmap, when we do a transition roadmap, we start with some pre-work and we start with each individual person figuring out who’s gonna be a participant, successors, transitioners. What do you really want in your life? What do you see in your life? What would a great life look like for you, for your spouse, for you as a couple, for your family?

for your extended family, for the business, for your employees, for your clients, if you have partners or other investors for those people. What does it look like? We ask that of each person and then we bring people together and they actually share what they want in their lives. It’s the foundation of the collective why. What are we trying to accomplish as

as a group, a community of people that care about this business and that are going to come together to be that community to make sure it goes forward as people transition out and others come in. So…

When we get to this, usually have an immersion, kind of a retreat, and we get together. So we get all these people together that are doing this work on their ideal lives and what they’re looking for. And they share in that. And as people learn what’s happening, ⁓ it’s fabulous what happens. They start to have empathy for each other, and they start to understand each other, and they start to create this

vision, collective vision on what they’re trying to do and why. Before these retreats happen, basically every time ⁓ we have members who are coming say things like, I’m not willing to come and I’m not willing to open up and I’m not willing to share. don’t want anybody to see what I’m thinking or what I’ve done. I’m like, okay. Fear.

isolation. You can stay there if you want to, that’s okay. However, it’s really pretty unproductive to do that. ⁓ We have people saying our transition or right, our parents, they’ll never change. They never share any information with us. They always keep it tight to the best. ⁓ This is probably a waste of time.

and we’re probably not going to get anywhere and we’ve tried this before. Mindsets, we’ve tried it before, it hasn’t worked, it’s not going to work again, they’re never going to change. ⁓ Where’s that coming from? The person, the successor feeling not good enough, not trusted by the parents, ⁓ that we can’t get there from here, lot of frustration. ⁓

And to me, that’s sadness sitting there.

because someday the information will come out, someday they will know it. And it’s a great thing to do to have the owner bring it forward while they’re still around and have these conversations, change those mindsets. So as we go through this immersion, the first part of the immersion program, it’s incredible how open people become and how much communication happens and how literally like,

Some of these fears that are weighing them down dissipate. So our fears, we have greater fears when we’re in isolation. And that just happens. We just spin up our thoughts and they become bigger and we become more afraid. And then we really don’t move forward. And sometimes they’re surface fears. We just put a label on them without diving deep.

into what’s really behind that. So as we wrap up this podcast, I just want to invite you ⁓ to reflect and invite you to look at your fears and look at what’s really keeping you from moving forward and look at what’s keeping you from trusting and what’s keeping you from doing what you’ve always done. If you’re an entrepreneur, you don’t let things stand in your way.

You just go for it. Calculated risks, yes, but most entrepreneurs I know are pretty bold and they take calculated risks and they go for it. But for some reason, and I think it’s because it’s so important because people’s lives are at stake in this, people’s emotional, physical. ⁓

Yeah, spiritual beliefs and or spiritual well-being, they’re at risk when you go through these transitions. So I think that the transitions for some reason, people don’t move forward and not moving forward just to me is probably a bigger mistake than addressing the issue. So again, invite you to take a look and do some introspective.

work on what’s going on for you. then I’d also, always want to invite you into our Evolve program named for a reason. We’re trying to help people evolve from where they are today in their thinking to where they want to be in their thinking. And Evolve has the immersion program in it as the beginning spot, and it also has some implementation work. So, I invite you to take a look at that. We’re here to always help people move forward because, ⁓ you know, my personal mission is to help people live their best lives and we don’t live our best lives when we’re fearful and not moving forward. I’ll see you next time.

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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