Grace Trail Experiences
Pause with purpose. Connect with intention. Move forward with hope.
Designed for organizations, teams, conferences, and communities seeking a meaningful way to support reflection, resilience, connection, and wellbeing.
A Different Way to Connect, Reflect, and Grow
Created by Anne Jolles and powered by ChatGPT, the Digital Grace Trail Walk offers a guided introduction to the Five Questions of Grace Trail®—wherever and whenever you're ready to begin.
Before You Begin: If you already have a ChatGPT account, clicking the link should take you directly to the experience.
If you don't have a ChatGPT account you may encounter a message that says you don't have access, simply click "Retry" and follow any prompts that appear.
Once the experience opens, type your responses where it says "Ask anything" and the Digital Grace Trail will guide you through the Five Questions one step at a time.
Virtual Grace Trail Experience
Virtual Grace Trail Experiences are available on a limited basis for teams, organizations, and communities seeking a guided reflective experience across locations.
Ideal for: Groups of 10–100, Can be customized for leadership, wellbeing, caregivers, veterans, students, or community reflection.
*One planning call required.
Limited availability
"Grace Trail doesn't tell people what to think or how to feel. It creates the space for them to hear their own answers — and find their footing."
— Anne Jolles
“Anne was our keynote speaker for a daylong professional development retreat for coaches and therapists. She combined sensitivity, compassion, professional coaching knowledge, and humor to create a dynamic and engaging learning experience for all attendees. I can’t say enough about the fabulous connection she made with our entire community.”
— Joan Schulman, Coach, Consultant, Facilitator
NorthEast Dare To Lead Facilitators Retreat /
Brené Brown Facilitators
Additional Grace Trail Experiences
Grace Trail can also be adapted for:
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Retreats
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Leadership workshops
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Team wellbeing programs
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Conference and convention pop-up trails
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Fundraising events
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Community healing experiences
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Guide training
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Multi-site Grace Trail experiences
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Special programs for veterans, caregivers, students, healthcare workers, and leaders
Availability: These offerings are currently considered on a selective basis and may require a planning team, approved Grace Trail materials, and a one-time event agreement or license.
Grace Trail at the Massachusetts Conference for Women
Inspiration is powerful. Action is transformational. At the Massachusetts Conference for Women, Anne Jolles guided attendees through the Grace Trail experience, giving them the opportunity to pause, reflect, and take the first step toward meaningful personal insight before returning to the conference.
Not Sure Where to Begin?
Start with the Digital Grace Trail Walk or complete the inquiry form below.
"In just a few minutes, Anne created a cohesion in the group that hadn't been there before. She helped me broaden my thinking about my business and my life. Bright, effective, down to earth, and genuinely engaging, Anne was one of the most memorable parts of our three-day event."
— Szifra Burke
EXPLORE THE QUESTIONS. DISCOVER WHAT'S POSSIBLE
The Five Grace Trail Questions are simple enough for anyone to answer and meaningful enough to revisit throughout your day and your life. Each time you walk it is a different experience.
Through Anne's facilitation, participants experience the questions together, often discovering new insights, deeper understanding, and a shared framework they can continue using long after the experience ends.
Gain Perspective
People often discover answers they already have—but haven't had the space to hear.
Create Psychological Safety
The Five Questions create a simple structure that allows people to participate at their own comfort level.
Start Better Conversations
Simple questions create openings for discussions that often wouldn't happen otherwise.
Connect Beyond Roles
Shared reflection helps people see one another beyond titles, positions, and assumptions.
Build a Shared Language
Organizations, teams, and communities gain a framework they can return to long after the experience ends.
Move Forward with Intention
Participants leave with greater awareness of what matters, what needs attention, and what comes next.
“Grace Trail is part of our culture. It helps keep our team above the line and able to work through even the most devastating circumstances. It keeps us focused on what we can do to help those we serve — instead of what’s out of our control.”
— Christine McSherry, CEO, Casimir LLC