E171: Bootstrap Boogie. The Race Between Doubt and Trust

Sometimes leadership looks like running a race you’re not sure you’re ready for.

In this episode, Cynthia shares a story from her 17k Bootstrap Boogie run — a course made of grass, beach, clay, shale, trail, and boardwalk — and every emotional terrain in between. What began as a morning of self-doubt became a powerful reminder of what happens when we trust our presence more than our pressure.

Through moments of laughter, falling, friendship, and reflection, Cynthia explores how physical challenges often mirror our inner ones: how to stay grounded when the path changes beneath you, how to lead beside others instead of ahead, and how to blaze new trails for those who’ll follow.

This isn’t just a running story. It’s a love letter to courage, community, and self-trust — and a reminder that leadership is, at its heart, love in motion.

Listen if you’ve ever doubted your strength, questioned your “yes,” or needed someone to ring the cowbell for you.

Access the Playlist (aka musical love letter) here.

Chapters

• 0:05 Invitation To Get Unfiltered
• 0:56 The Race And Why It Matters
• 2:13 Morning Doubts And Shared Nerves
• 3:22 Presence On Every Changing Surface
• 4:02 Falling, Focus, And Real Leadership
• 5:00 Friendship As Fuel For Courage
• 5:57 Gratitude, Age, And Generational Freedom
• 7:02 The Cowbell, Support, And Vows
• 8:12 Love In Motion And Your Next Step
• 9:39 A Playlist, An Invitation, And Closing

Transcript

Cynthia : 0:05

Welcome to Uncharted and Unfiltered, The Journey Back to You. I am Cynthia Jameson, your host, and this is where we break free from the noise and dive deep into what truly matters. You. If you're tired of the shoulds, the expectations, and the pressures to fit into a mold that doesn't serve you, you're in the right place. This isn't a podcast about easy answers or sugar-coated advice. This is your invitation to reclaim your path, embrace the unknown, and become the bold, unapologetic version of yourself that's been waiting to show up. It's time to get unfiltered. Let's get started. Hello, hello, friend. It is Cynthia and welcome back to the Uncharted and Unfiltered A Journey Back to You podcast. I hope that you are having the most amazing day. I'm going to be completely honest, right here, right now, it is 10 o'clock in the morning, and I am in my recording studio, aka my closet, and I haven't yet prepared for the day. And there's a reason for that. And that brings us to today's episode. So if you were listening in real time, yesterday, which was Saturday, November the 1st, I ran a 17-kilometer race. And it was called Bootstrap Boogie. The name alone makes me smile. Because honestly, what better metaphor for life in leadership is that? Just think about it. And I'm going to share with you a little bit about the course. So there was grass, there was beach, there was waves, there was clay, there was shale, there was trail, there was boardwalk, all of it. And every surface demanded something different. Balance, focus, adaptability. It was a course that was made of everything. And maybe that's exactly the point. Now, let me go back because when I woke up yesterday morning, I was not feeling the love. Let me be super clear. You know, have you ever had those days when you questioned why you said yes to something? I looked at my running gear and I thought to myself, what was I thinking? Now, by the time that I met up with the others in the parking lot where we had agreed to meet before we carpooled down, I had worked myself into a story. The one that whispers, you don't have to do this. You're not ready. You could just go home. You get to make a choice here. But then the chatter and the energy of the group, when I experienced that, I realized that I wasn't alone. Those who had run before this event were buzzing with so much excitement. You're gonna love it. This is going to be amazing. And those who hadn't, well, they were right there with me, doubting life choices. And there it was, the very first lesson of the day. When we share our fears, they lose their power. Because once we started, everything shifted. It was hard, yes, absolutely, but not in the way that I had expected. This wasn't just a physical challenge, it was an attentional challenge. But every surface demanded that I be fully present with the surface. Every step was a decision. Every breath was a reminder to stay grounded in my body, not in my mind. And about halfway, I think it was about halfway, I fell. I wasn't the first. Um, I think three out of eight of us in our group fell. It wasn't anything dramatic. It was just a stumble, a little scrape, and a small reminder that distraction costs us balance. Now I was incredibly grateful that it did not trigger my vertigo. I was able to brush myself off. And I thought to myself, there is a story in this. And there was. Because leadership, like running, isn't about staying upright the whole way through. It's not. It's about getting back up, it's about choosing your focus over your fear, and it's about staying in the race. Now, the best part of the day wasn't the race itself. It was the people, friends, their laughter filling the air, their presence steadying you when your footing wobbles, friends who remind you that leadership isn't always about being out in front. Sometimes it's about running beside. Sometimes it's about running behind. Sometimes it's allowing yourself to catch up. And as we move through the woods, I kept thinking so much to myself, I love these humans. Their stories, their hugs, their energy, their enthusiasm. And I love gifting that same presence back to them. The kind of presence that says, I see you, I'm with you, I'm here for you. That's what leadership really is: a shared rhythm of care, of courage, and belonging, love. Now, somewhere around kilometer 15, I think it was, I just stopped and I looked around. I got the trees, the ocean air, the laughter, all of it echoing through the trail. And I felt this deep wave of gratitude for being 59 years old, for still being willing and able to blaze new trails, both literally and generationally. Because I wasn't just running for me. I was running for every woman in my family who's never had the chance to choose this kind of freedom for my children, stepchildren, grandchildren, to show them what's possible when you stop letting the world tell you what you can do and start trusting yourself to decide instead. Now, as we neared the finished line, I saw my husband standing there, which was such a surprise to me. Cowbell in hand. Now I gotta tell you, he loves a good cowbell. He really, really does. And if you're ever at an event with him and he has the cowbell, you might need some earplugs. And hours had gone missing in the move. So he bought a new one just for that. And earlier that morning he had volunteered to help participants park. Now, here he was, ringing that bell, cheering for every single solitary soul that ran by him. And his joy was echoing across the finish line. He had the privileged position of being able to say, You're just two minutes away. And I thought to myself, this is what support looks like. And little caveat, I was reminded of our wedding vows because this is what we agreed to was to always support each other in our growth, in our dreams, in becoming the best best versions of ourselves that was possible. And as I stepped back mentally and noticed that I was surrounded by people who love you enough to invite you into new experiences, sometimes hard ones, because they see something in you that you haven't fully seen yet. And that to me is a mark of a great leader. People who lift you into a more powerful story of yourself and who cheer you on when you stumble, walk, or sprint. That is leadership. That's love in motion. And so here's my question for you today. Where in your life are you being invited into something that feels uncertain or hard, but could actually lead you into a fuller version of yourself? And who's ringing the cowbell for you, who's cheering you on when you are looking for and finding your stride? Or maybe who needs you to ring the bell for them? Because leadership isn't just about proving our strength, it's about trusting our presence. And every time we show up messy, doubtful, real, we blaze a new trail of what's possible for ourselves, for others, for the world. And so this morning, as I reflected on the race, I felt so called to create something to capture the energy of it all, the laughter, the courage, the connection. So I made a playlist. Something I I can't re recall the last time that I had done something like that. But it's a little musical love letter to the incredible friends who ran beside me and to anyone who is out there finding their own rhythm again. You can find the link in the show notes and may it lift you, ground you, and remind you that you are not running alone, even when you think you are. Thank you for running this one with me. And until next time, stay curious, stay kind, and keep coming home to yourself. Make it a great week. 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.