E188: Why Did I Wait? A dream, a pen, and a lesson in self-trust.

Nobody is actually stopping you, and that can be both freeing and confronting. I start with a dream that left me thinking about a familiar kind of stuckness many high-performing leaders live with: the sense that you’re under constant pressure, even when the external facts don’t fully explain the weight you feel. The shift that matters is simple but profound: pressure exists, but suffering often comes from what we add to it, the stories, expectations, proving, and the need to get it right.

From there, I unpack how waiting becomes a leadership trap. Waiting for the promotion, the title, the invitation, recognition, certainty, or validation. I share a coaching story where a “typical” timeline quietly turns into an identity, and how a small realization can break the spell: an opinion doesn’t have to become your reality. That’s where inner authority starts to come back online, and where leadership begins to feel grounded again.

Then we move into two metaphors that tie everything together: the pen and the microphone. The pen asks, who is writing your story? The microphone asks, are you willing to use your voice even while fear sits beside you? We define ambiguity, uncertainty, and fear, and why real leadership development isn’t about eliminating them, it’s about building self-trust that holds steady in their presence. If you’ve been outsourcing your knowing, this is your reminder: the mic is already on.

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Transcript

A Dream That Exposes Stuckness

Cynthia 0:06

Hello, hello, and welcome back to Uncharted and Unfiltered. Have you ever had a moment where you realized that no one was actually stopping you? Not your boss, not your team, not your organization, not your family, not even the circumstances you were standing inside of. And yet, somehow you felt stuck. Something interesting has been happening lately. This is actually the second episode in a row that started with a dream. Now, whether you believe dreams mean something or don't mean something doesn't really matter. What does matter is that sometimes they reveal truths that we are already carrying, truths that we haven't quite said out loud yet, that we have been living without fully seeing. And this dream showed me something that I think every high-performing leader needs to

Pressure Made Inside Our Minds

Cynthia 1:12

hear. The pressure isn't coming from outside of us, the pressure is being created inside of us. And that is a very different problem. Because if we are creating it, we can stop creating it. So many leaders tell me that they're under pressure. And to be fair, they are. Deadlines are real, difficult conversations are real, organizational change is real, kids are real, aging parents are real, the economy is real. And if you're listening to this while folding laundry, walking the dog, driving to work, or hiding in your car because it's the only quiet place in your day, that's real too.

Waiting For Permission And Validation

Cynthia 2:02

But here's what I find fascinating. Two people can experience the exact same circumstance and have completely different experiences of pressure. Why? Because one is experiencing the circumstance and the other is experiencing the story. I know. Your brain is probably going, no, Cynthia, the circumstance is definitely the problem. And maybe. But let's look a little closer. In this dream that I was having, there was a leader who didn't acknowledge me. She knew that I was new, she knew that I was there, and yet she didn't acknowledge my presence. Now, what struck me wasn't her behavior, it was mine. Or maybe more accurately put, my lack of behavior. Because when I've reflected on the dream, the question that emerged for me was why did I wait? Nothing in the dream prevented me from introducing myself. It didn't prevent me from speaking, nothing prevented me from occupying my own space. The only thing present was my assumption that I should wait. And that got me wondering how many of us are doing exactly that. Waiting, waiting for the promotion, waiting for the title, waiting for the invitation, waiting for recognition, waiting for validation, waiting for us to feel more confident, more prepared, more ready. Waiting until all the conditions are perfect before we allow ourselves to fully arrive in our own lives, our own leadership, our own presence. Meanwhile, life keeps moving. And this is where I think many, many leaders get trapped. We say I'm under pressure, and that's often true. Pressure exists, but pressure and suffering are not always the same thing. Pressure might be a deadline, a difficult conversation, a presentation that's coming up, an organizational change, but suffering, suffering often comes from what we add. The stories, the expectations, the proving, the performance, the fear, the need to get it right, all these different attachments we have to it, the need to be liked, the need to not disappoint anyone, the need to hold everything or everyone together. And the pressure isn't always the circumstance. Often it's the meaning that we have attached to it.

When Opinions Become Your Timeline

Cynthia 4:59

Now, I was with a client recently who had been promoted and was already thinking about what comes next, of course, because this is the way our beautiful brains work. She told me that she had been told it typically takes about three years to reach the next level. And what fascinated me wasn't the timeline, it was what happened next. Without realizing it, she had started relating to that timeline as though it were her identity, as though her growth had been put on pause, as though there was nothing left to do except wait. And then in the coaching conversation, she had this beautiful realization. She said, just because my manager said it doesn't mean it has to become my reality. And I almost laughed. I didn't. And not because it was funny, but because that's how it happens. The angels aren't singing, there's no fireworks, there's no great big giant breakthrough. There's this tiny realization, oh, I've been treating an opinion like a fact. And haven't we all done that? Someone says, it takes years, or you're not ready, or that's unrealistic, or people like you don't do that. That's my favorite one. And before we know it, we are rearranging our entire future around a sentence someone else said. The pressure wasn't created by the timeline, the pressure came from accepting and believing that she had to live inside of someone else's version of the story. And

The Fountain Pen Means Authorship

Cynthia 6:47

this is what brings me to the my favorite part of this dream that I've had. Someone handed me a click pen. And I said, no, thanks. I am intentional about the pens I use, which sounds slightly ridiculous until you know me. I love all the colors, I love all the pens. And I reached into my bag and I pulled out a fountain pen. Now I have nothing against click pens. I have used them. A click pen is functional, it's convenient, it's interchangeable, it's disposable. Anyone can use one. A fountain pen is different. You choose it. Or in my case, it was gifted to me. My wonderful husband gifted it to me as I began this writing journey. And you care for it. It slows you down. It asks you to be intentional. It leaves a distinct mark. And somewhere in the middle of reflecting on pens, I realized that this wasn't about pens at all. It was about authorship. Who gets to write the story? Who gets to decide what's true? Who gets to determine what's possible in our beautiful lives? Because every day we are writing something. We are writing stories about who we are, what we're capable of, what we deserve, what's possible for us, what has to happen before we are allowed to trust ourselves, and how many of us have handed the pen away to expectations, to approval, to old identities, to organizational cultures, to family conditioning, to fear, to the version of ourselves that learned how to belong. Self-abandonment is giving someone else the pen. Self-trust is taking it back. The goal is not to control the story. The goal is simply to remember that it is your story to write for yourself.

Self-Trust Gives You A Voice

Cynthia 9:02

The more I sit with this dream, the more I realize how it's connected everything for me. Because here I am sitting in front of a microphone, recording a podcast that came from a dream. And maybe, just maybe, that's the second part of the message. The pen writes the story. The microphone gives us a voice. Just sit with that for a moment. Because I know a lot of people who know what's true for them and never say it. They know, they just don't trust themselves enough to speak. And that breaks my heart. And in the dream, someone handed me a lapel microphone, but I didn't know how to use it, but I wasn't worried. I knew that I'd figure it out. And that's very different from feeling certain. Self-trust is not confidence that everything will work. Self-trust is confidence that you will meet whatever happens. It is not, I know the answer. It is, I trust my capacity to find one. That's leadership, that's adulthood, that is trusting yourself.

Ambiguity Uncertainty And Fear

Cynthia 10:22

And as I reflected on the microphone, that got me to thinking about expression. Thinking about that got me to thinking about expression, and then that got me thinking about how often we use the words ambiguity, uncertainty, and fear as though they are interchangeable, and they're not. Ambiguity is not knowing which path is best or right, or the one that you should take. And if you're anything like me, your brain immediately says, perfect, let's analyze all 47 possible outcomes before making a decision, which, by the way, has never once made me feel better and never once was it helpful. Uncertainty is not knowing what will happen. Fear is what our mind does with both. And here's what I have noticed: most leaders spend enormous amounts of energy trying to eliminate ambiguity and uncertainty, but neither one of them can be eliminated. Leadership is ambiguous, life is uncertain, the future has always been and will always be unknown. The real work isn't eliminating that. The real work is developing a relationship with yourself that remains grounded in the presence of all of

Stop Outsourcing Your Inner Authority

Cynthia 11:54

it. That's self-trust. Now, here this here's the part that stayed with me long after I woke up. You never ever had dreams like that, which is like later on in the day, you're still feeling it. In the dream, someone said to me, It's interesting that she doesn't want you to say anything. And yet, I was already wearing a microphone. The mic was already on. I couldn't stop thinking about that. Because what if that's true for us too? What if the microphone has been on this whole time? We have experience, we have wisdom, we have perspective, we have a voice, and we're still waiting, waiting to be chosen, waiting to be invited, waiting to be acknowledged, waiting to be certain, waiting to feel ready. And if you're listening right now thinking, well, not me, that's usually the sign I'm talking about you. Because the people with the most wisdom are often the least convinced they have it. And if we're honest, we are not usually waiting because of the circumstance. We're waiting because of what we've made the circumstance mean. Maybe we don't have all the information, that's your friend ambiguity. Maybe we don't know that how things will unfold, that's your friend uncertainty. Maybe we're afraid, and that's your friend fear. And none of those mean we shouldn't speak or shouldn't do the thing we want to do. They simply describe the conditions under which leadership happens. Leadership has always required ambiguity, it has always required uncertainty, it has always required fear. The question isn't whether they're present. The question is, do we trust ourselves in their presence? Because self-trust isn't finding your voice once fear disappears, it's finding your voice while fear is still sitting beside you. The microphone is already on. The question is, are you waiting for permission that no one was ever supposed to give back to you? The more I sit with this dream, the more I think it revealed the difference between self-abandonment and self-trust. Self-abandonment says, let me check everyone else's map before I trust my own inner compass. Self-trust says I can listen to others without abandoning myself. A grounded leader isn't the leader with the least pressure. A grounded leader is the leader who no longer mistakes an external circumstance for internal authority. They stop waiting, they stop proving, they stop outsourcing their knowing, and little by little, this work is never done, they come home to themselves. Because the journey back to you isn't about becoming someone new. It's about remembering who was standing there all along. And maybe that's what the dream was trying to tell me. The pen was already in my hand, the microphone is already on. Perhaps the same is true for you.

Reflection Questions And How To Connect

Cynthia 15:36

Before we finish today, I would love for you to consider this. Where in your life are you waiting for acknowledgement, permission, certainty, or validation that may never come? And what would change if you trusted yourself first? And if you're realizing as you listen that you have been waiting, there's no need to wait, beat yourself up about it. If you've been waiting for permission or certainty or for someone else to tell you what you already know, that's exactly the work I help leaders explore. Not through more strategies, templates, or performance hacks, but by helping them reconnect to themselves. Because self-trust isn't something we think our way into. It is something we practice, one decision, one conversation, one truth, one moment at a time. And if that conversation feels like one you're ready to have, I would love to support you. Until next time, this is Cynthia Jameson, and this has been Uncharted and Unfiltered A Journey Back to You. Remember, the mic rate may already be on. The question is whether you're willing to use it. I hope that you're walking away feeling more aligned with your true self, more confident in the choices ahead, and ready to leave the safe path behind, knowing you've got everything you need within. Remember, the journey to you isn't about finding one perfect direction. It's about trusting yourself enough to explore all of it. If you're ready to dive deeper, join me for the next episode and don't forget to subscribe so that you never miss the next step on your path. I invite you to join my mailing list at www.cynthia JamesonCoach.ca, where we'll deepen our relationship and you can claim your copy of your inner compass, a guide to charting your course to authenticity. Until next time, stay unfiltered, stay true, and most importantly, stay you.