A Life Walked in Grace
"I think I've been walking Grace Trail my whole life. I just didn't know it had a name yet."
Meet Anne
Life has a way of inviting us into moments we never expected.
Mine has included extraordinary joy, uncertainty, motherhood, caregiving, career changes, loss, hope, and more than a few new beginnings.
Looking back, I can see how each chapter shaped the work I do today. Long before Grace Trail had a name, I was learning how to keep moving forward—with curiosity, compassion, courage, and grace.
What Life Has Taught Me
Over the years, I've learned that the secret to life isn't having all the right answers. It's learning to ask better questions.
Curiosity changes everything.
When we stop trying to have all the answers and begin asking honest questions, something opens. We become more present, more compassionate, and more able to see possibilities we may have missed before.
Walking deepened that understanding for me. Some of my clearest moments have come while moving through nature—when the noise quiets, perspective returns, and there is room for the next step to emerge.
Along the way, I’ve also learned to become a collector of awe. Even in difficult seasons, beauty has a way of reminding us what is still possible.
Walking Beside Others
Long before Grace Trail became a movement, my work centered on helping people navigate change with greater clarity, courage, and compassion.
As an occupational therapist, certified professional coach, speaker, and facilitator, I’ve had the privilege of walking beside thousands of people through meaningful transitions—in classrooms, hospitals, conference halls, boardrooms, communities, and on the Trail.
Through it all, one thing has remained remarkably consistent:
People don’t always need someone to tell them where to go. Sometimes they need the space—and the right questions—to find their own way forward.
The Work Continues
What began as a personal practice during one of the most uncertain chapters of my own life grew into five questions—and from those questions, Grace Trail took shape.
Today, those questions are creating places for reflection, connection, and hope in communities across the country.
"You don't have to have the answers to understand Grace.
You can be the answer by living your life with curiosity, compassion, and courage."
- Anne Jolles
Coming Full Circle
Sometimes the places that shape us become the places we are called to serve.
During one of the hardest chapters of my life, while my son was deployed to Afghanistan, walking became a place to process uncertainty, ask questions, and find my footing. That practice would eventually help inspire Grace Trail.
Now, that journey is coming full circle.
The VA Boston Healthcare System’s Brockton campus is preparing to install the first Grace Trail within the Department of Veterans Affairs—a lasting place for Veterans, families, caregivers, and staff to pause, reflect, and find their next step.
Dedicated in memory of Michael M. Lawson, the Trail is a meaningful reminder that even our hardest experiences can become something that helps another person move toward hope.
Along the Way
A journey shaped by service, curiosity, and a growing movement to help others find their footing.
2000
Grace Trail is Born
The Grace Trail questions emerge during a personal season of uncertainty, offering a grounded way to pause, reflect, and move forward with intention.
2001
Certified Professional Coach
Anne becomes a Certified Coach through the International Coach Federation and completes training with Coaches Training Institute.
2001
Private Coaching Practice Begins
Anne enters private practice and has since coached more than 2,000 clients.
2012
Massachusetts Conference for Women
Originated “Coaches Corner,” delivering complimentary professional coaching to thousands of women nationwide.
2012
A Son's Deployment to Afghanistan
During her son's deployment, Anne found comfort in walking and reflection. The experience later influenced the creation of the first Grace Trail path.
2012
The First Stones Are Placed
Anne places hand-written reflection stones along a walking path in Plymouth, Massachusetts—the future home of the Plymouth Seaside Grace Trail.
2013
International Coach Federation of New England
Life Coach of the Year · Director Award for Distinguished Service
2015
National Book Publication & Recognition
Publishes "Grace Trail: Find Your Footing and Move Toward the Life You Were Meant to Live".
2015
Massachusetts Conference for Women
Led an interactive Grace Trail experience with six stations and 45 volunteers.
2012
2012
2016
FIGMENT Festival, Boston
Grace Trail installation on the Rose Kennedy Greenway.
International Book Awards — Amsterdam & New York.
2012
2017
Wicked Local ARTY Award · TEDx Wilmington
Recipient of the ARTY Award. Delivered TEDx talk “Cracking the Grace Code.”
2013
2015
2020
Boston University Sargent College
Named Alumnae of the Year.
2015
2016
2020-2022
The First Licensed Custom Trail Installations
During the COVID-19 pandemic, communities sought new ways to foster connection and well-being. The first licensed Grace Trail installations take root across the country, including UMass Boston (MA), Beth Israel Deaconess Hospital–Plymouth (MA), East Lyme (CT), West Woods School (CT), Alpine Shores (WI), Navarino Nature Center (WI)
2017
2020
2023
The First Grace Trail on Private Property
Green Trees Farm (TX) becomes the first private Grace Trail installation and the first location to feature three unique licensed Grace Trails on a single property
2020-2022
Massachusetts Conference for Women
Created a 50-foot Grace Trail experience engaging over 13,000 attendees.
2023
2024
2024
The Birthplace Becomes Permanent
The Plymouth Seaside Grace Trail is officially licensed, and the original hand-painted stones are replaced with engraved 3,000-pound granite boulders featuring the Grace Trail questions.
2024
2024
A Network of Trailblazers
Licensees begin gathering through community calls and shared initiatives, gaining access to ideas, resources, encouragement, and connections with others bringing Grace Trail to life in their own communities.
2025
2025
2025
National Grace Trail Month Is Established
National Grace Trail Month is created, aligning with Mental Health Awareness Month and activating communities across the country through walks, events, conversations, and opportunities for reflection.
2025
2026
2025
The First Vermont Grace Trail
The Hard'ack Grace Trail is licensed and installed in St. Albans, becoming Vermont's first Grace Trail and the northernmost installation.
2026
2026
Grace Trail Is Coming to the VA
Installation is scheduled for the Michael M. Lawson Grace Trail at the VA Boston Healthcare System, U.S. Department of Veterans Affairs – Brockton Campus, creating the first memorial Grace Trail and honoring a legacy of service, sacrifice, and remembrance.
Move Toward the Life You Were Meant to Live
Grace Trail: Find Your Footing and Move Toward the Life You Were Meant to Live brings the five questions off the Trail and into everyday life through personal stories, reflections, and simple practices for navigating change.
A Note from Anne
Thank you for taking a little walk with me.
If these years have taught me anything, it's that life isn't about avoiding hardship. It's about learning how to keep moving through it—with curiosity, compassion, courage, and grace.
I don't believe we need to have all the answers. I believe we need the space to ask honest questions, listen for what is true, and trust the next step when it appears.
Grace is not always graceful, but it is always worth it.
However you found your way here, I am glad you did. I hope to see you on the Trail.
With gratitude,
