My Services
Whether working one-on-one, with leaders, or in retreat settings, my work is grounded in the same belief: lasting change begins with presence, self-awareness, and the integration of body, heart, and mind.
Individual Coaching
Develop greater presence, clarity, and self-understanding through one-on-one coaching that helps you navigate life's challenges with intention, courage, and compassion. Read more here.
Leadership Coaching
Support for leaders seeking to lead with greater presence, authenticity, courage, and effectiveness in times of complexity and change. Read more here.
Retreats
Opportunities to step away from the demands of everyday life, reconnect with yourself, and deepen your capacity for presence, reflection, and renewal. Read more here.
Kind Words About My Work
Mollie Matteson, Environmentalist
​
"Annie is a natural listener, a natural leader, and, because she sees that we all are already intelligent, and also need support to realize our potential, she is a natural collaborator. ... Her integrity and courage inspire me."
Terri Swain, HR Consultant
​
"Annie O'Shaughnessy is a brave and honest person who will inspire you because she is so human, and at the same time, such a beautiful and brilliant soul, as we all are. Her tenderness and zeal for life is a balm for those who are ready to live a more passionate and true life."
Anne-Marie Hober
"Thank you for cracking open that window and letting in a change of air into my self-imposed prison! Thank you, Ann, from the bottom of my heart!"
My Services
Individual Coaching
Individual coaching offers a dedicated space to slow down, pay attention, and explore what is happening beneath the surface of your daily life.
Together, we examine the patterns, assumptions, habits, and ways of relating that shape your experience. Through mindful self-observation, compassionate inquiry, and developmental coaching, we cultivate greater awareness of the intelligence of the body, heart, and mind and how these dimensions influence our choices.
Clients often come to coaching during periods of transition, uncertainty, growth, or challenge. Some are seeking greater purpose and alignment. Others want to improve relationships, navigate difficult decisions, or free themselves from patterns that no longer serve them.
Rather than focusing on fixing what is wrong, our work centers on reconnecting with the wisdom, clarity, and resilience that are already present within you.
Leadership Coaching
Leadership is ultimately an inner practice.
The way we lead is shaped not only by our skills and knowledge, but by our assumptions, emotional patterns, blind spots, and capacity for self-awareness. The greatest leadership challenges are often developmental rather than technical.
Drawing on adult development, restorative practices, mindfulness, neuroscience, trauma-informed approaches, and the Enneagram, I partner with leaders to strengthen their ability to navigate complexity, build healthy relationships, communicate effectively, and respond skillfully under pressure.
My coaching supports leaders in developing greater awareness of how they make meaning, how they show up in relationships, and how they influence the systems around them. Together we explore practical challenges while also cultivating the deeper presence and discernment required for sustainable leadership.
Clients include superintendents, district leaders, school administrators, nonprofit leaders, and individuals leading change within their organizations and communities.
​
​
Retreats
Retreats offer something increasingly rare in modern life: time and space.
Away from the noise, urgency, and distractions of daily responsibilities, participants are invited to slow down, listen deeply, and reconnect with what matters most.
Drawing from mindfulness, circle practice, rites of passage traditions, reflective inquiry, nature-based experiences, and community dialogue, these retreats create a supportive environment for self-discovery, personal growth, and meaningful connection.
Some retreats focus on specific themes such as the Enneagram, self-observation, leadership, life transitions, or personal renewal. Others simply offer an opportunity to pause, reflect, and reconnect with the deeper currents of one's life.
Participants often leave with a renewed sense of clarity, purpose, and connection—to themselves, to others, and to the lives they want to create.