The CEO Sage · 2026-06-15 · 16 min
Key moments - from our scoring
Substance score
29 / 100
Five dimensions, 20 points each
Chris Plackey examines the paradox many women entrepreneurs face after building multi-million dollar businesses: the very success that was supposed to bring freedom instead becomes a cage. Operating from fear - of losing key team members, revenue streams, clients, or industry position - successful founders often find themselves stretched too thin and emotionally exhausted, much like Elastigirl frozen in place in The Incredibles. Plackey argues this happens because founders remain too operationally close to their business rather than stepping into visionary leadership. She draws on her own 17-year tenure at a coaching organization, where reframing her question from "When is it safe to leave?" to "What does relentless pursuit of the work and life I love look like?" became the catalyst for launching her own practice and Hawaii retreats. Through client examples - including one who fired key team members and doubled revenue in a single launch, and another whose supposed irreplaceable employee's departure freed her to hit $1M+ launches - Plackey demonstrates that what founders fear losing often prevents rather than enables success. The episode invites established entrepreneurs to shift from protective, scarcity-based thinking to expansive, possibility-focused questions.
By staying too operationally close (in the weeds) rather than stepping into visionary leadership, founders become dependent on revenue and team members, creating fear-based decision-making that prioritizes protecting what exists over creating what's next.
The first draws fear-based answers that reinforce staying; the second opens possibility-thinking and actionable next steps, as Plackey discovered when the second question led her to plan Hawaii retreats and launch her coaching business.
Yes, according to Plackey's examples: one client doubled her launch revenue and hit $1M+ after her supposedly irreplaceable team member left, discovering the person had actually been a constraint rather than an asset.
Success can become boring or misaligned with their evolving needs when they've made themselves so operationally integral that they're vital but unseen, trapped between importance and invisibility.
Operating from fear keeps you generating reasons why you can't leave the box you're in; shifting to possibility-thinking allows you to imagine what could be better than you've ever imagined.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode offers some genuine psychological insights about successful entrepreneurs becoming trapped by their own success and the role of fear in stagnation. However, it relies heavily on repetition of the core thesis ('what if it could be better') and lacks substantive frameworks or novel operational advice for B2B leaders. The two client case studies provide some concrete evidence but are thin on detail and metrics.
you build it and then you become almost trapped in it
we become dependent on the revenue, on the salary on, and then all these other people are dependent on you. And there is a weight to that
The core idea - that successful founders can become trapped by fear and their own success - is a common theme in coaching and leadership content. The reframing technique (changing questions from fear-based to possibility-based) is directly attributed to Tony Robbins and is well-worn advice. The Incredibles metaphor and the overall narrative structure feel familiar rather than fresh or contrarian.
the primary question, which is born out of Tony Robbins work
What if it could be better? What if it could be better than you ever imagined simply by changing the question that you ask yourself
This is a solo episode featuring the host (Chris Plackey) reflecting on her own experience and unnamed client anecdotes. There are no external guests, operators at scale, or practitioners with verifiable track records discussed. This is a monologue coaching call format rather than a substantive interview.
Well, well, hi, this is the CEO Sage. I'm Chris Plackey
I have another client who just was boxing me last night
While two client case studies are mentioned, they lack concrete specificity. One client 'made over a million dollars in one launch' and 'doubled her performance,' but there are no timelines, initial baseline numbers, or details on what changed operationally. The federal grants reference is vague. Most claims rely on general statements rather than named examples, metrics, or dates beyond 'just this week.'
she doubled her performance in this launch that she just had and made over a million dollars in one launch
I have several clients right now who have operated their business for years on federal grants which have been decimated
As a solo monologue, there are no host-guest interactions, follow-up questions, or productive disagreement. The episode is structured as a therapeutic/coaching monologue with rhetorical questions posed to the listener rather than genuine inquiry. There is no adversarial testing of ideas or willingness to challenge the narrator's framework.
But what if it could be better?
Are you willing, I would invite you to use your journal today and just answer that question
Computed from the transcript - who did the talking, and the words that came up most.
You built something incredible. You made a thing that didn't exist. You're running a multi-million-dollar business, and yes, that's magic. But somewhere along the way, the dream you chased became a box you're trapped in. Kris calls this the quiet crisis. You've achieved the success you set out to create, but now you're drowning in it. You can't leave because too many people depend on you. You can't pivot because you're afraid of losing the revenue, the security, the key people. So you stay, spinning on all the ways it could fall apart. Sound familiar? In this episode, she's talking to the woman who built her empire and is now wondering if this is it. Is this the whole thing? Can you ever be free? And she's offering a completely different way to think about it.
Transcribed and scored by The B2B Podcast Index.
Well, well, hi, this is the CEO Sage. I'm Chris Plackey, and I'm happy that you're back. So I am in the process of thinking about next year, which feels so far away, but it isn't. And by next year, what I mean is the fall I started New Sage Mastermind, for lack of a better word, Think Tank experience in September.
And so I've been thinking a lot about what this coming experience means and it's taken me down a couple of different paths. And so I thought I would share with you today one of the things that has been sort of present for me and also through the work I've done with some of my clients, which I think is super fun. And so that's why I called this one. But what if it could be better?
So, you know, one of the things that happens as we create our lives is we become. Well, let me back up. What happens is we have ideas about what we want in our life and what we want in our business and how we want that to all be right. We have all these ideas.
And as a woman who is an entrepreneur, who is a visionary, who sees horizons, other people don't see you, you are empowered internally to believe that you can do it. And here you are having done it, you did it, you built it, you made a thing that didn't exist. You are magic. It really is magic.
And I will stand by that. But then something seems to happen and along the way, things change. Along the way, the success that you've realized in this business, if you're running a multi million dollar business, you have realized a level of success that is amazing. It's brought you and your life a lot of fortune and good experiences, incredible opportunities.
It's done, done the same for people that work for you. It's, it's had served a community, whoever those people are that are your customers or your clients. And what can happen is that vision that brought you there, you get, you build it and then you become almost trapped in it. And for a lot of us, it's because we're, we stay too, too close to the ground.
We still, we stay in the weeds, we become an operator, right? We started with a dream. We started with a vision. We started with all that tenacity and aspiration and inspiration.
And then it is achieved through that level of, through all of that part of who we are. And then it now is the box that we live within. And we become dependent, we become dependent on the revenue, on the salary on, and then all these other people are dependent on you. And there is a weight to that, that for a lot of women, becomes unbearable.
Other people and yourself start to have an expectation of how well you will produce and perform. And so now the intention around what you're doing is to perform in what you've created rather than dream about what's coming, what's next. And when we sit there, then, in this place of achievement and success, we have fear around the loss of it. And that can look like a lot of things.
Fear of losing the money, the revenue, the security, the people, the vital people, the key team members, the clients, the customers, the industry, the colleagues. There's this fear that takes over. And oftentimes when I meet my clients, where they are is misery. They're drowning in the very thing they built for freedom.
But they're so afraid of what will happen if they lose or let go of any part of it. And so what they do is they. Is. Is.
Is they spin on what could happen. What. I don't even know what I'll do if so and so isn't here anymore. If they quit, if they're not part of this team anymore.
I don't even know what I'll do if this happens in my industry and this is no longer available. I have several clients right now who have operated their business for years on federal grants which have been decimated. Right. That wasn't even on the list.
And now they're having to punt and figure that out. I don't even know what I'll do if consumer behavior changes. I don't even know if this one client that has been my biggest client for the last five years drops me. So there's this suspension, there's this fear.
And so I imagine it as. I don't. If you're not a Incredibles, an Incredibles Pixar movie fan, this may not mean anything to you, but Ms. Is incredible.
She could stretch and do all these things, right? And she. She's incredibly stretchable and malleable, but she can be stretched to the point of, like, stuck. Like, she.
There's this one scene where she's suspended. She's stretched all the way out. She can't move. And I just think that I think of.
Of you that way sometimes, that we. We put ourselves in that position and we have so much fear, even though we're completely maxed out because we painted a picture of what. What. Of how horrible that could be.
And so I bring us back to. But what if it could be so much better? What if that key person on your team Leaving could be the best thing that ever happened. What if that line of revenue getting turned off could be the best thing that ever happened.
What if the industry changing and you having to pivot within it could be the best thing that ever happened? The woman that you were when you started this business, she would believe me. But you've. You've built a business that you are also dependent on.
It's not just dependent on you, you're dependent on it. And that relationship can get quite unhealthy because it smothers your creativity and your magic. And what we need from you is that what you need from you, is that so? What if it could be better?
And I have so much evidence of clients that I work with all the time where it's better. Just this week, right? Just this week, I've had a client tell me that she has opted through our conversation to focus on being in pursuit of right, of making radical decisions and radically, radically choosing what she needs to choose in order to have a business that she loves. And that has meant doing some really, really scary things and firing some really, really important people and dealing with some outcomes that she did not want to deal with.
And yet she is emboldened. She is, like, powerful because she's like, I got all sorts of things I gotta jump through. But you know what? I don't care.
Because I am radically choosing to build a business that I love. And that means I gotta go this way. And now she has replaced herself with the one client that took the majority of her time. So she has so much more freedom.
She has bought her freedom through the asset of another human that she never thought she could do. She thought she would lose the client. She hasn't lost the client. I have another client who just was boxing me last night, showing me her results from a challenge that she did this week, this time last year, she was literally in a puddle because her key team member, the person that she thought she could not operate her company without literally ghosted her, left her.
Heartbreaking, heartbreaking. And she had all sorts of other compounding circumstances that she was like, I'm never gonna. How am I ever gonna make this work? I don't know how to do this.
I don't know how to do this alone. I am. I'm not this good, all these things. And last night she sent me the spreadsheet of her performance over the last, I think, 18 months.
And she doubled her performance in this launch that she just had and made over a million dollars in one launch. And she did it just her and her team, this key person that was a part of her team, what if that person was actually preventing her success? She thought she was contributing to it. We have to be willing to consider that it could be better.
But it is the downfall of so many of us when we achieve a certain level of success because we freeze, we become more fearful than we do. Adventurous. But the adventure and the risk is what got you here. It's how you manifested what you already have.
So when we know we want to curate more, it isn't through guarded protective energy. It's through expansive belief and magic. And so I work with women who are ready to do that, who are ready to have their comeback story, who are ready to live and work in a way that is joy filled. There was a time many years ago when I'd been with the company that I was with for 17 years and I had been leading and managing and building a coaching organization within it and doing all sorts of coaching.
I started coaching years ago and I knew I wanted my own coaching business. I knew that's what I wanted. But I had so much fear. And I kept asking myself, but what am I going to do?
I, how am I ever going to know when is the right time to leave? I, I make the most money here of my family, I have all the benefits, I have a lot of security and safety with this company. How am I ever going to know when it's time to leave? And that was such a terrible question, right?
Because it was drawing on the answers were going to draw fear. Well, you can't leave, you have all the health care, but how are you going to protect your family? You're the primary earner. How are you going to pay your mortgage?
It just kept being this cycle of fear that kept me. And so I was at a mastermind and we were practicing writing a new question, the primary question, which is born out of Tony Robbins work. And through that work I wrote a question. And the question I wrote is what does relentless pursuit of the work and life I love look like?
What does relentless pursuit of the work and life I love look like? And I wrote that in my journal that I made and I wrote all of the answers. Coaching incredible people, hosting retreats in Hawaii. I planned my first Hawaii retreat at that mastermind, mastermind with that question.
What if it could be better? What if it could be better than you ever imagined simply by changing the question that you ask yourself. Everything that got you to where you are is still within you. And it's normal for you to have built a multi Million dollar business to have built this exceptional role in the world.
Being sage, right? Someone who is known for what she does, that other people come to you, they seek you out. You are the woman in the room that they all know can give them the insight they need, the mentoring they need. That is an aspirational place to be and to.
At a level to achieve. But what if you're not done? What if you don't have to just keep what you have, but this is a place to build off of and it's okay if you don't know what that is? I, I think so many of us don't.
I think so many of us who achieve this level of success become bored with it, tired of it. And sometimes that's because we've continued to leave, make ourselves so integral to the operation of it that we are like absolutely required to be a part of it. But we feel very unseen and very invisible in some sort of weird way. Like we're vitally important, but really unseen because there isn't an alignment anymore with your needs.
And that is a, that is a role you can step out of. And I know that a woman who can create what you've already created has so much more in her. But we're not going to create if we're standing in a. In a box that we're afraid to lose.
We're going to keep coming up with reasons why we can't leave the box. And so this is kind of a quiet invitation that might echo what you might be experiencing as a quiet crisis, which is that you, you can move out of where you are. You can discover your next chapter, your new rally, your whole new plan. But to do so, we have to be willing to change the frame that you're using to think about it.
And we can't be thinking out of the context of where you are or where you've been, but we have to instead think in the context of what could be possible. What if it could be so much better? Are you willing, I would invite you to use your journal today and just answer that question. If it could be so much better, what would that look like?
And just write it all down. What if it could be better than I ever imagined? What would it look like? What could that be?
If it was better than ever? Give it a think. I'll talk to you next time.
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Your Thriving Matters to Everyone29 / 100Get What You Want38 / 100Stop Looking Outside45 / 100The Relaunch & What This Actually Is36 / 100The Courage to Stop A New Chapter in Leadership and Life
