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 all of us into moments we never expected.
Some moments have been filled with extraordinary joy. Others have challenged me in ways I never imagined. Like so many people, I've walked through uncertainty, motherhood, caregiving, career changes, loss, hope, and beginning again.
Looking back, I can see every chapter was quietly preparing me for the work I do today. Long before Grace Trail had a name, I was simply learning how to keep moving forward—with curiosity, compassion, 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.
Life has taught me that curiosity changes everything.
The moment we stop trying to have all the answers and begin asking honest questions, something begins to soften. We become more open. More present. More willing to see possibilities we couldn't see before.
Walking only deepened that understanding. Some of my clearest moments have come while moving through nature, where the noise quiets, perspective returns, and the next step has room to emerge.
I've learned to become a collector of awe. Even in difficult seasons, beauty has a way of reminding us what's still possible. That's what Grace Trail has always been for me—not a place to find perfect answers, but a place to create enough quiet to hear the ones that were already there.
Walking Beside Others
Long before Grace Trail became a movement, my work was helping people navigate change with greater clarity, courage, and compassion.
Over the years I've had the privilege of walking beside people through some of life's most meaningful transitions. Sometimes as an occupational therapist. Sometimes as a coach. Sometimes as a speaker or facilitator. And sometimes simply as another person learning to navigate life alongside them.
Across classrooms, conference halls, hospitals, boardrooms, walking trails, and communities, I've learned something remarkably consistent: people don't need someone to tell them who they should become... they need space to remember who they already are.
Everything Life Taught Me Eventually Became Grace Trail
Today, I have the privilege of partnering with schools, healthcare systems, businesses, Veterans organizations, and communities to create places where people can slow down, reconnect, and move forward—one question at a time.
The Work Continues
Today that work continues through partners with communities, organizations, and leaders to create experiences that help people reconnect—with themselves and one another.
"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, Grace Trail became the practice that helped me find my footing when everything else felt uncertain.
Today, the VA Boston Healthcare System's Brockton campus is preparing to install the first Grace Trail within the Department of Veterans Affairs, creating a lasting place for Veterans, families, caregivers, and staff to pause, reflect, and find their next step.
Dedicated in memory of Michael M. Lawson, this Trail is a deeply meaningful reminder that our hardest experiences can become something that helps others 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".
2012
2015
Massachusetts Conference for Women
Led an interactive Grace Trail experience with six stations and 45 volunteers.
2012
2016
FIGMENT Festival, Boston
Grace Trail installation on the Rose Kennedy Greenway.
International Book Awards — Amsterdam & New York.
2012
2013
2017
Wicked Local ARTY Award · TEDx Wilmington
Recipient of the ARTY Award. Delivered TEDx talk “Cracking the Grace Code.”
2015
2015
2016
2020
Boston University Sargent College
Named Alumnae of the Year.
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
2023
2024
2024
Massachusetts Conference for Women
Created a 50-foot Grace Trail experience engaging over 13,000 attendees.
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
Explore the stories, reflections, and five questions that inspired Grace Trail—and discover a simple practice for navigating life's challenges with greater hope and intention.
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,
