Weekly reflections on leadership, identity and dignity
Coaching for leaders navigating complexity without losing themselves
Leadership, identity and dignity in an age of fracture — for people carrying real responsibility and wanting a place to think clearly, speak honestly, and decide who they want to be in the middle of it.
Coaching for leaders navigating complexity without losing themselves
Coaching for leaders navigating complexity without losing themselves
From Staying Human
I write a weekly Substack called Staying Human, where I explore leadership, identity, and what it means to remain human when institutions, relationships, and expectations are under strain.
These stories and reflections are about leadership, love, dignity, and what it means to stay awake in difficult times.
These are stories, questions, and practices drawn from real life — from families, organizations, and the places where people are trying to remain connected across deep difference.
Many people first encounter my coaching through these reflections. Coaching is where those same questions can be explored personally, in real time, and with practical support.
Who I work with
My clients are often senior leaders, nonprofit executives, founders, physicians, attorneys and professionals navigating moments of responsibility, transition, or institutional pressure.
They do not come because they lack skill.
They come because the situations they face cannot be solved by expertise alone.
This leadership requires clarity, steadiness, and the ability to lead without losing themselves.
How the work unfolds
Our work explores three interconnected dimensions:
Identity — Who you are beneath roles and expectations
Relational — How you lead, communicate and navigate conflict
Systemic — The pressures, institutions, and power dynamics shaping your decisions
Together, these create space for clearer choices, steadier leadership, and action aligned with what matters most.
About Michael
Michael Painter (JD, MD, Cherokee Nation of Oklahoma) brings a lifetime of layered identities into his leadership coaching — not to impress, but to model what it means to lead with full humanity in times of tension, change, and complexity.
I bring many lives into this work: coach, physician, lawyer, husband, father, son, and citizen of the Cherokee Nation of Oklahoma. I am also a gay man who has lived inside both profound belonging and painful difference.
Those intersections shape how I understand leadership.
They have taught me that who we are — our identities, loyalties, and histories — is always present in how we lead, whether we acknowledge it or not.
My work is grounded in that truth: that the deepest leadership happens not when we flatten ourselves, but when we learn to hold the full complexity of being human with courage and care.
Working Together
If you’re navigating a moment of change, conflict, or moral tension — in your leadership or your life — we can explore it together.
Coaching with me is a space for:
honest conversation
careful listening
reflection that leads to wiser action
If you’re curious about working together, you’re welcome to reach out.
My Coaching Vision
Together we explore what leadership means in your unique life and context — not just what goals you want to achieve, but how you want to show up in complexity, challenge and change.
Our work is grounded in presence, reflection, real experience — weaving your identities, values, and responsibilities into a humane practice of leadership.
I am trained broadly and have worked in a variety of fields, including law, medicine and philanthropy.
I coach using the renowned Hudson Institute of Coaching methodology following the ethics of the International Coaching Federation.
I bring my experiences as a leader, physician, lawyer, community member, senior philanthropy officer, father, son, Indigenous citizen, gay man, husband, and friend.
Start a conversation
If you are navigating a leadership moment, personal transition, or a season that requires deeper reflection, I invite you to begin with a conversation.