What if your biggest challenge became your greatest catalyst for growth?
Three accomplished leaders open all the way up and share how they turned their ‘Oh Sh!t’ moments into powerful ‘Thank You’ realizations.
- Matt Hall, owner/founder of Hill Investment Group
- Rose Thompson, CEO of ButcherJoseph & Co.
- JP Revel, owner/founder of Lelander + MajorMajor
As leaders, we all face similar struggles, doubts, and opportunities, but we rarely if ever actually talk about it. The goal of these articles and this roundtable is to start bringing these necessary conversations into the open showing we are not alone in our challenges.
Through these leaders’ stories I hope you find the courage to embrace your own struggles, recognize opportunities for growth, lead with renewed energy and purpose.
Watch the full conversation here:
I hope you enjoy watching as much as I enjoyed being a part of it.
Here is an overview of the areas we dove deeply into:
The Turning Point: From Crisis to Catalyst
Each shared transformative moments that reshaped their paths. Matt’s story was particularly striking: “I was sitting in my doctor’s office, and she opened the door. And I heard her say to her admin person, cancel the rest of my appointments.” This moment, when Matt was diagnosed with a rare form of leukemia at 32 just after leaving a great job to start his own investment firm, became a catalyst for profound change. The diagnosis forced him to slow down and reevaluate his priorities, leading to a new perspective on life and leadership.
Similarly, Rose described her realization in late 2022 that she had been “white-knuckling” her life for nearly three years. “I had just focused so much of my energy on managing urgency and minimizing frenzy,” she shared. This awareness led to a pivotal decision to reconnect with herself, ultimately booking a getaway that became a transformative experience.
Embracing Vulnerability as a Leadership Strength
JP highlighted the power of authentic leadership: “I think of a leader who put up a veneer of toughness and strength, and actually showed me what was real and became vulnerable enough to tell me their fears and the worries.” This approach, while initially uncomfortable, ultimately built trust and encouraged team support. JP noted that it took him years to embrace this vulnerability, but it has since unlocked tremendous potential in his leadership.
Rose echoed this sentiment, emphasizing her core value of “wholeheartedness” in leadership. She explained, “That’s what allows me to be my authentic self, that’s what allows me to be a catalyst for their best self, is when I am shoulder to shoulder in deep connection with someone.” This approach has helped her build strong relationships with her team and navigate challenging times.
Reframing Challenges: The “Oh Sh!t to Thank You” Mindset
Matt’s perspective on uncertainty evolved dramatically post-diagnosis. He learned to “lean more into uncertainty” rather than fear it, recognizing that in entrepreneurship, “you get paid and rewarded for uncertainty.” This mindset shift was crucial in transforming crises into opportunities for growth and innovation. Matt shared how he now approaches challenges with a more clinical view, focusing on clearly stating desires and detaching from immediate impacts.
JP’s turning point came when his office was closed, and he was tasked with shutting everything down. This experience made him realize that employment offers only a “thin veneer of security,” leading him to become a freelancer and eventually start his own business. He learned to bet on himself despite initial lack of self-confidence, a lesson that has shaped his entrepreneurial journey.
The Ongoing Journey of Self-Reflection and Growth
Each of them openly shared their current struggles, demonstrating that growth is continuous. Rose admitted, “Not shaming myself. I’m working on it every day, sometimes every hour.” She explained how high expectations in various roles led to a habit of self-shame, and she’s now learning to embrace imperfection.
Matt’s 2024 motto, “zoom out,” reflects his effort to ask better questions rather than always having answers. He explained, “I think as I’ve matured as a leader, I think people are thinking about this with all the AI tools as well. It’s like, maybe it’s less about having all the answers and more about asking like the best possible questions.”
JP courageously addressed childhood trauma, stating, “I’m realizing that I’m very grateful that childhood trauma is very fixable.” He’s putting in the work, having tough conversations with his parents, and working on understanding how his childhood experiences shaped his current behaviors and thought patterns.
Elevating Energy and Authenticity in Leadership
The conversation emphasized how a leader’s energy directly impacts their team and organization. “We imprint our identity into our organization… you want to see our strengths, there they are, you can see our weaknesses, there they are.” This recognition underscores the importance of self-awareness and personal growth in effective leadership.
Rose highlighted the importance of “unspoken, it’s never benign.” She emphasized how this concept encourages everyone to embrace vulnerability, not just herself as a female leader who tends to be more open. “That’s the way we build real trust with each other. That’s the way we demonstrate we’re vested in each other’s best interest and our collective interest,” she explained.
Change Starts With You
My goal with my writings and this conversation is to help you open pathways to see how you can become a leader that is more impactful and more purposeful, and more healthy in a way that you can actually enjoy the journey.
These open, vulnerable discussions serve as a testament to the shared challenges and triumphs we all face in our leadership roles. The energy and insights shared by Matt, Rose, and JP demonstrate that by opening up about our struggles and growth, we can elevate not just ourselves but those around us too. We may not be able to change the entire world, but we can certainly change our little piece of it.
Based on the overwhelmingly positive feedback we received from those that logged into the live, it’s clear that these topics, this conversation resonated deeply. Looking ahead, I am excited to explore the possibility of continuing these discussions, featuring other leaders on their own growth journeys.
Fear, doubt, and shame are extremely destructive raw materials for leadership. Each of them thrive in secrecy and darkness but neutralized and shrivel away when we have the courage and vulnerability to expose and explore them together.
As a leader, you must go first.
Lead with your own work, with your own energy.
Only then can you unleash the true power of those you have the honor of leading.
Lead With Energy,
Derek