About Anne
The Heart Behind Grace Trail
®
A Life That Shaped Grace Trail
The story of Grace Trail didn't begin with an organization. It began with one woman navigating life the same way many of us do—one honest question at a time.
A Note from Anne
You may be here because you are curious about me—or because something about Grace Trail resonated with you. Before sharing any titles or milestones, I want you to know this: Grace Trail did not begin as a concept or framework. It began as my life.
​
During one of the most challenging seasons I had ever known, a single word came to me quietly in my kitchen. Within that word, I began to see five simple, deeply human questions. They did not feel new. They felt remembered.
​
Walking—especially outdoors—helped me step away from the noise and reconnect with myself. Movement gave me space to listen, understand what was happening, and find my footing.
​
As I began sharing these questions with others, I realized how many people were searching for the same thing: a way to step out of the noise, hear themselves again, and find their next step.
​
I came to understand that people do not always need to be fixed. They need space. Sometimes, a few honest questions can help us remember what matters and take the next step.
​
Grace Trail grew from that understanding. Whether experienced on a physical trail, with others, or through personal reflection, it offers a simple way to move through life with curiosity, connection, compassion, and hope.
​
However you found your way here, I am glad you did. I hope to see you on the Trail.
​
With gratitude,
"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
Anne's Work in The World
For more than 25 years, Anne Barry Jolles has helped individuals, organizations, and communities navigate life's most meaningful moments through reflection, leadership, and human resilience.
Anne's work has been shaped by far more than professional experience. It has been shaped by the seasons that tested her most—raising a family, walking beside people through uncertainty, advocating for those she loves, and discovering that life's hardest moments often become our greatest teachers.
Coming Full Circle
What once marked one of life's hardest seasons now stands as a reminder of what can grow from resilience, hope, and the courage to embrace what's possible.
When Anne's son returned home from combat in Afghanistan, she searched for answers, advocated within the VA, and navigated one of the most uncertain chapters of her life. Throughout it all, the five Grace Trail questions became something she leaned on every day—helping her keep moving forward one honest question, one breath, and one step at a time.
Years later, Anne returned to the VA for a very different reason. Grace Trail is coming to the VA Boston Healthcare System's Brockton campus as the first Grace Trail within the U.S. Department of Veterans Affairs. For Anne and her husband Jon, this is more than a project. It is a return—a place born from military family's lived experience that will soon invite Veterans, families, caregivers, and staff to pause, reflect, and find their own way forward.
Michael M. Lawson
Memorial Grace Trail
Fall 2026 Installation
The Work Continues
Today, her work spans community spaces, national conferences, education, healthcare, Veterans initiatives, and public life, always rooted in presence, listening, and lived experience.
Over The Years
Anne’s life and work have unfolded across many chapters—teaching, coaching, writing, motherhood, advocacy, and community building. Together, those experiences shaped the philosophy behind Grace Trail and the work it has become today.
2000
2001
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.
Certified Professional Coach
Anne becomes a Certified Coach through the International Coach Federation and completes training with Coaches Training Institute.
2001
2012
2013
2012
2015
2016
2015
2017
2020
2024
2020-2022
2023
2012
Private Coaching Practice Begins
Anne enters private practice and has since coached more than 2,000 clients.
Massachusetts Conference for Women
Originated “Coaches Corner,” delivering complimentary professional coaching to thousands of women nationwide.
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.
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.
International Coach Federation of New England
​Life Coach of the Year · Director Award for Distinguished Service
National Book Publication & Recognition
Publishes "Grace Trail: Find Your Footing and Move Toward the Life You Were Meant to Live".
Massachusetts Conference for Women
Led an interactive Grace Trail experience with six stations and 45 volunteers.
FIGMENT Festival, Boston
Grace Trail installation on the Rose Kennedy Greenway.
International Book Awards — Amsterdam & New York.
Wicked Local ARTY Award · TEDx Wilmington
Recipient of the ARTY Award. Delivered TEDx talk “Cracking the Grace Code.”
Boston University Sargent College
Named Alumnae of the Year.
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)
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.
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.
2025
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
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
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
National Grace Trail Month Continues to Grow
In its second year, National Grace Trail Month expands with guided walks, community events, media features, and trail activations across the country in support of Mental Health Awareness Month.
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.
Find Your Footing and Move Toward the Life You Were Meant to Live
Whether you're discovering Grace Trail for the first time or looking to explore it more deeply, Anne's book offers the full story behind the philosophy, the experiences that shaped it, and practical guidance for bringing the five questions into everyday life.