Today we’d like to introduce you to Esther Bailey-Bass
Alright, so thank you so much for sharing your story and insight with our readers. To kick things off, can you tell us a bit about how you got started?
This journey began long before I realized it. It wasn’t until I was in my mid-40s that I started asking myself what I truly wanted to do for a career. When I finally began exploring this question, I turned to family and friends for insights into how they perceived me. One response in particular sparked both my curiosity and surprise: they saw me as a teacher. My immediate reaction was, ‘Absolutely not!’ The idea of teaching made me think of a classroom full of children, which was far from anything I’d imagined for myself.
But the idea lingered. I became curious about what ‘teaching’ might mean beyond my initial concept. I began to explore my roots and asked myself, Where do I come from? I come from a family of teachers—wisdom-keepers, actually. That realization shifted something inside me and opened my mind to a new way of seeing what it might mean to be a teacher.
Around that time, I noticed a buzz in Nashville—many people were interested in becoming coaches. Coaching was something I knew little about and had never experienced myself. But my curiosity was piqued, so I began researching and having conversations about it. Soon, I realized that coaching was the path I was meant to take, and I found the places to learn more and grow in this direction.
It’s been a long journey of personal and professional growth, one met with resistance, fear, and doubt. But each of those challenges has brought me to where I am today, with a renewed sense of purpose and clarity. And while there is still more I want to do, I’m excited to continue expressing myself in this way and fulfilling my mission.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
Well, at first, it was quite easy. The dopamine hit I experienced during coach training lasted a long time—I was energized, inspired by new concepts, and excited to develop skills that sparked countless ideas. But with that excitement came fear around claiming a new identity and stepping into this role with confidence. For the first time in a long time, I felt I was becoming self-authored, intentionally designing my future. I set a target date to leave my full-time job and launch my business. I met that date, and I thought I had planned well.
However, a few months into the new year, once the excitement of resolutions faded, it became clear that I hadn’t planned as thoroughly as I’d thought. I quickly realized I didn’t fully understand what it meant to run a business. Running a business takes courage, fortitude, and a network of support. It requires determination, consistency, and a commitment to continuous learning, experimentation, and resilience in the face of failure.
Many of my challenges have been self-imposed—battling internal noise, limiting beliefs, doubts, and fears. Each day is an opportunity to uncover, discover, and learn something new about myself. And yet, the thrill of this journey is unlike anything I’ve experienced before. I’m in it for life because it gives me life.
Thanks – so what else should our readers know about EBB ‘n Flow Leadership?
EBB ‘n Flow Leadership is a boutique consulting, facilitating, and coaching firm founded on the principles of self-determination, interdependence and self-assurance. We’re dedicated to cultivating leadership that’s rooted in authenticity, self-awareness, and inclusive values-based practices. I work primarily with executive directors, emerging leaders, board members and untitled leaders within for-profit and non-profit sectors including social service organizations, small and mid-sized businesses guiding them to build cohesive, collaborative relationships within their teams and organizations. My approach centers on the belief that everyone is a leader and through leadership development, coaching and Circle facilitation, I help clients create an environment where each voice contributes to a shared mission and purpose.
I provide coaching, leadership development trainings, and facilitation to individuals and teams, helping them to lead authentically, align with their values, and build resilient ecosystems. My work includes one-on-one coaching, team coaching and immersive VIP experiences, as well as programs that focus on communication, self-awareness, and relationship building. I also offer Circle facilitation as a powerful tool for fostering trust, open dialogue, and a sense of togetherness within teams. Additionally, my digital course such as Lighting the Fire Within: A Journey to Divine Intelligence guides individuals in connecting with their inner wisdom for empowered decision-making.
I specialize in cultivating cohesive, collaborative teams and helping leaders forge effective stakeholder relationships. Using frameworks like Positive Intelligence, ORSC tools, the Hogan Assessment and Circle facilitation, I support leaders in enhancing their self-awareness, clarifying their values, and building trust-based connections with their teams. My work also emphasizes whole-self leadership, a concept that encourages leaders to being their full selves to their roles and fosters a culture of inclusivity and togetherness.
Clients know me for my intuitive, heart-centered approach to coaching. I create a space where leaders feel safe to explore and embrace their authentic selves, and they appreciate my ability to listen generously and ask thought-provoking question that lead to deep insight. Through Circle facilitation, I help foster a sense of connection and belonging, enabling teams to deepen their relationships and collaborate meaningfully. My clients describe me as trustworthy, insightful, and authentic and they know I’m deeply committed to their growth.
What sets my business apart is the intentional way I integrate values alignment, Circle facilitation, Positive Intelligence and inclusive leadership principles into engagements. I don’t just teach leadership; I help clients create ecosystems within their organizations where everyone feels empowered to lead and contribute. My work is not about giving leaders the answers but guiding them to their own inner wisdom, helping them foster self-awareness, build resilience and navigate complex relationships with confidence. Additionally, my background in ORSC and Positive Intelligence, combined with certifications in Co-Active and Hogan Assessments, allows me to offer a holistic approach to leadership development.
I’m incredibly proud of the sense of community and mutual support that my brand fosters. My clients consistently say they feel seen, heard and valued, and I believe that sense of togetherness is a core element of my brand. Circle facilitation, in particular, has been impactful in creating this bond within in teams, helping individuals feel connected and committed to a shared purpose. Building a business that emphasizes “a leader in every chair” and helps others cultivate inclusive and empowering work environments is deeply fulfilling. This brand essence carries through in my client work, group facilitation, and digital courses – every aspect reinforces a commitment to authentic, mindful leadership.
I want readers to know that EBB ‘n Flow Leadership is about more than traditional leadership coaching. It’s about helping leaders discover and connect with their values, fostering resilience, and building teams that thrive through collaboration and respect. My offerings include personalized one-on-one coaching, team coaching, Circle facilitation for fostering team unity and dialogue, and unique digital programs like Lighting the Fire Within: A Journey to Divine Intelligence, which empowers participants to connect with their inner guidance systems. My services are for leaders at every stage – from executive directors and board members to emerging and untitled leaders – and each offering is designed to help them bring their whole selves to their roles and make meaningful, lasting contributions.
We’d love to hear about how you think about risk taking?
Yes, I’ve taken significant risks. The first time I left my 18-year career in public media – a reputable and lucrative sales role to start my business, I nearly burned through all our savings and quickly realized I wasn’t financially positioned for the leap. With no concrete plan in place, I returned to full-time work within a year. But that experience taught me invaluable lessons about resilience, adaptability and the realities of entrepreneurship.
In July of 2023, I made the decision to take the leap again. Despite not being perfectly positioned financially, I was fueled by a desire for more freedom and I have more knowledge, experience and a solid foundation of resources and support. This choice wasn’t without its own risks, but I felt a renewed commitment to my vision and the impact I want to make.
While I’m still not exactly where I want to be, each day I face moments of fear, anxiety, uncertainty and doubt. Yet I continue to move forward toward my vision, gaining the strength to step out of my comfort, do something different and step forward into my future. This journey has shown me that stepping away from stability to pursue a calling requires both courage and patience, and I’m committed to building something meaningful and lasting.
Contact Info:
- Website: https://www.estherbaileybass.com
