Legacy Contemplation Opportunity

Annual Camino de Santiago Walking Retreats

#AnnualCaminoDeSantiagoEscape

Why do you walk the Camino de Santiago again and again every year? Because it’s my annual board meeting with myself.

Summary

In our fast-paced world of quarterly reports and constant digital connectivity, we rarely create space to contemplate our deeper purpose and legacy. Annual walking retreats along the Camino de Santiago in southwest France offer a powerful antidote, providing structured time away from daily demands to reflect on what truly matters. This article explores how these 7-day retreats create transformative opportunities for people seeking to align their remaining decades with their deepest values.

Key Takeaways:

1. Walking retreats create mental space for deeper life reflection, impossible in daily routines
2. Annual contemplation rituals establish consistent patterns for personal growth
3. The historic Camino de Santiago provides a proven framework for meaningful reflection
4. Walking in nature stimulates different cognitive processes essential for legacy thinking
5. Non-guided retreats allow for personalised contemplation at one’s own pace

The Modern Contemplation Crisis

When was the last time you asked yourself: “What am I really doing with my life?” Not in a late-night existential panic, but in a thoughtful, structured way with enough time and space to genuinely explore the answer?

For most of us, the honest response is “not recently enough.” We’re caught in what I like to call the “hamster wheel of immediacy”—running faster and faster without questioning whether we’re even on the right wheel. Between endless Zoom calls, family obligations, and the hypnotic scroll of social media, who has time to contemplate their legacy?

The trouble is, as we reach mid-life and beyond, this question becomes increasingly urgent. The math gets simpler: we’ve lived more years than we have left. Yet ironically, this is precisely when many of us are at our busiest, often at the peak of careers or juggling multiple family responsibilities.

“I’ll think about that when I retire,” we tell ourselves, as if deep reflection is a luxury to be postponed rather than a necessity for living well. But here’s the uncomfortable truth: without intentional contemplation, we risk spending our most productive decades building someone else’s dream rather than fulfilling our own purpose.

The Transformative Power of Walking

There’s something almost magical about walking. Not the hurried pace between meetings or the perfunctory lap around the block with the dog, but sustained, purposeful walking day after day.

Throughout history, great thinkers have recognised this power. Aristotle conducted his teaching while walking, forming what became known as the Peripatetic School. Nietzsche claimed that “all truly great thoughts are conceived while walking.” Thoreau found that his thoughts began to flow “the moment my legs begin to move.”

What these luminaries understood intuitively, neuroscience now confirms: walking fundamentally changes how we think. When we walk, especially in natural settings, our brain activates different neural pathways. The prefrontal cortex—our executive function centre—gets a well-deserved break, allowing more creative and contemplative parts of our mind to emerge.

Add to this the simple rhythm of left-foot-right-foot for hours each day, and something profound happens. The mind stops its frantic bouncing and settles into deeper patterns. Questions that seemed impenetrable in your office suddenly clarify themselves three days into a walking journey.

As one recent pilgrim told me with a laugh, “I spent ten years in therapy trying to figure out what became blindingly obvious on day four of my Camino walk.”

The Camino de Santiago Experience

There’s walking, and then there’s walking the Camino de Santiago. This ancient pilgrimage route has been traversed for over a thousand years, originally by religious pilgrims seeking the tomb of St. James. Today’s pilgrims come with diverse motivations—some religious, others spiritual in a broader sense, and many simply seeking clarity during life transitions.

What makes the southwest France route particularly special is its combination of breathtaking beauty and relative solitude. Unlike the more travelled Spanish routes, the French paths through charming villages and golden countryside provide space for genuine reflection without the crowds.

The Camino offers a unique paradox: it’s both a deeply personal journey and a communal experience. You might walk alone for hours, deep in thought, then share a meal with fellow pilgrims from around the world, exchanging insights and stories. This balance of solitude and connection creates the perfect conditions for meaningful contemplation.

There’s also something powerful about following in the footsteps of millions who came before you—each with their own questions, struggles, and revelations. The path itself seems to hold a certain wisdom, as if the collective seeking of so many souls has imbued the very dirt with purpose.

As one 62-year-old executive put it after completing the journey: “I’ve had fancy meditation retreats in five-star hotels and week-long strategy sessions in Swiss chalets. Nothing—absolutely nothing—compares to the clarity I found simply putting one foot in front of the other on the Camino.”

Annual Retreats as Life Anchors

Why annual? Because transformation isn’t a one-and-done affair.

Think of annual walking retreats as your personal board meeting—except instead of PowerPoint presentations and fluorescent lights, you get ancient paths and star-filled skies. It’s an appointment with yourself that becomes sacred through its regularity.

The first year might bring revelations about an immediate life challenge. The second might deepen into questions about your relationships. By the third, you might be contemplating your legacy in earnest—how you want to be remembered, what truly matters in the decades ahead.

Each journey builds upon the last. You return to certain questions with fresh perspective. You check in on commitments made during previous walks. You notice patterns in your thinking that might otherwise remain invisible.

Margaret, a 72-year-old who has completed three annual walking retreats, describes it as “watching my life from a loving distance.” She adds with a mischievous smile, “My children dread what changes I might announce after my ‘Camino week,’ but they’ve also told me they hope to adopt the practice themselves someday.”

This annual rhythm creates a framework for intentional living. The knowledge that you’ll be walking and reflecting every year gives you permission to “park” certain big questions until you have the proper space to address them. “I’ll walk with that next September,” has become a common refrain among regular pilgrims.

The Accidental Pilgrim

The rain had been falling steadily for three hours when Martin Ellsworth realised he had made a terrible mistake.

His boots—purchased hastily two days before departure—were not, in fact, waterproof. Each step on the muddy path sent another cold squelch through his socks. His expensive rain jacket had surrendered an hour ago, and water now ran freely down his neck.

This was supposed to be his triumphant mid-life reset. After twenty-seven years building a successful accounting practice, he had finally listened to his doctor’s warnings about stress. “Take a real break,” Dr. Meijer had insisted. “Not a business conference in Hawaii. Something completely different.”

The Camino de Santiago had seemed perfect on paper. Historical. Meaningful. A touch of adventure without requiring him to sleep in a tent or eat insects. The travel blogger had made it sound so enlightening.

The travel blogger had not mentioned blisters.

“This is ridiculous,” Martin muttered, adjusting his pack for the hundredth time. “I’m fifty-three years old. I run a sixteen-person firm. I don’t need to be slogging through mud to find myself.”

Ahead, the path disappeared into a grove of ancient oaks, their twisted forms dark against the grey sky. Martin stopped, seriously contemplating turning back. His phone had no signal, but surely he could find a road, flag down a car, find a train station…

“First Camino?”

The voice startled him. A small woman with silver hair emerged from behind, moving with surprising speed for someone who must have been in her seventies. She wore a simple poncho and carried a walking stick adorned with scallop shells.

“Is it that obvious?” Martin asked, attempting a smile.

“Only to someone on their twelfth,” she replied, eyes crinkling with amusement. “I’m Elaine. The trick is to accept the weather, not fight it. You’re already wet—might as well enjoy the rain.”

“Martin. And enjoying the rain seems like a stretch.”

She laughed. “May I walk with you a while? These old knees appreciate conversation as distraction.”

They moved together under the canopy of oaks, where the rain softened to a gentle patter. Elaine asked no personal questions but shared stories of her previous pilgrimages—the German professor who carried stones representing his regrets, the young couple who alternated carrying their child’s favourite stuffed animal to be blessed at Santiago.

“Why do you come back?” Martin finally asked. “Haven’t you ‘found yourself’ by now?”

Elaine’s laugh was like wind chimes. “Oh, I don’t come to find myself. I come to lose myself—all the identities and roles I accumulate each year. Mother. Grandmother. Retired teacher. Widow. Out here, I’m just Elaine again.”

Martin considered this. Who was he without his title, his firm, his reputation? The thought was both terrifying and curiously liberating.

That evening, warmed by a wood stove, Martin found himself surrounded by walkers from different countries. His wet clothes hung drying alongside those of a Brazilian artist, a Canadian nurse, and a Japanese retiree. They shared simple food and complex stories.

No one asked what he did for a living. No one checked their phone. Instead, they discussed what had called them to this path, what questions they had.

When Martin admitted he didn’t really know why he’d come, just that something felt missing, heads nodded in understanding rather than judgment.

By day four, the skies had cleared and so had something in Martin’s mind. The rhythm of walking had quieted the constant churn of work thoughts. His feet had toughened. He’d given his expensive watch to a young pilgrim whose phone had died, realising time moved differently here.

Each morning began with a simple question he’d learned from Elaine: “What wants to be known today?” Then he would walk, listening for answers in the crunch of gravel, the calls of birds, the stories of fellow travellers.

On the sixth day, climbing a steep hill outside a medieval village, Martin suddenly stopped. The realisation didn’t come as a dramatic epiphany but as a quiet certainty: he had been measuring his life all wrong.

His firm’s growth, his impressive client list, his careful retirement calculations—none of these reflected what truly mattered to him. The numbers balanced, but the meaning didn’t.

At the summit, looking out over rolling hills that had witnessed centuries of pilgrims, Martin sat on a stone wall and began to write in the journal he’d previously ignored. He wrote about his children, grown now and pursuing their own paths. About the pro bono work that had always given him more satisfaction than his highest-paying clients. About the woodworking hobby he’d abandoned fifteen years ago because it “wasn’t productive.”

When Elaine found him there an hour later, she didn’t interrupt his writing. She simply placed a scallop shell beside him and continued on her way.

That evening, at he dinner table, walkers were sharing their “Camino moments”—those instances of clarity or connection that had made the journey worthwhile. When his turn came, Martin surprised himself.

“I realised today that I’ve spent my life helping others plan for a future they never fully inhabit,” he said. “Including myself. I’m an expert at deferring life.”

The table quieted.

“This path has been here for a thousand years,” he continued. “People walking, thinking, questioning. I’ve been so focused on accumulating that I forgot to ask what it’s all for.”

A young woman across the table nodded. “So what will you do differently?”

Martin smiled. “I’m coming back next year, for starters. And the year after that. I want this to be my annual board meeting with myself. The rest… I’m still figuring out. But I know it involves more walking and less worrying.”

Later that night, Martin stood outside under stars brighter than any he’d seen in decades. He felt simultaneously smaller and more significant than he had in years. Whatever came next would be different. The path had shown him that much.

When he returned home the following week, his colleagues noted a change they couldn’t quite name. His children remarked that he laughed more easily. His calendar now had a permanent block for the first week of September each year—non-negotiable.

And in his office, replacing the framed accounting license, hung a simple scallop shell.

[End of featured story]

Beyond Professional Success: Finding Deeper Purpose

What Martin discovered in our story reflects what many mid-life and older adults encounter—a growing awareness that professional accomplishments, while valuable, don’t address our deeper questions about meaning and legacy.

We spend decades climbing the proverbial ladder, only to sometimes discover it’s leaning against the wrong wall. The metrics we’ve used to measure success—promotions, portfolio values, property—suddenly seem incomplete when we contemplate what we truly want to leave behind.

Walking retreats create a unique opportunity to step outside these conventional measures. When you’re reduced to a body in motion, carrying only essentials, different priorities naturally emerge. The questions shift from “How am I doing?” to “Who am I becoming?” and “What matters most?”

This isn’t about rejecting career success or material comfort. Rather, it’s about putting these achievements in proper perspective within a more holistic view of a well-lived life. It’s about ensuring that the story you’re writing with your life aligns with your deepest values—not just with external expectations.

As one pilgrim in his 60s memorably put it: “I came to the Camino wondering if I should sell my business. I left understanding that was the wrong question entirely. The right question was: how do I want to use the time I have left?”

The From Troubled to Triumphant Retreats

You might wonder why I emphasise that my retreats are non-guided. Wouldn’t expert leadership enhance the experience?

Not necessarily. The most profound insights often emerge when we’re given structure without prescription—a container for exploration rather than a directed tour.

My 7-day Camino walking retreats provide the logistical framework—accommodation, route guidance, emergency support—while leaving the actual journey entirely your own.

As an adult with decades of life experience, you bring your own wisdom to the path. You know your questions better than any guide could. What you need is time, space, and the freedom to follow your own rhythm—sometimes walking in silence for hours, other times engaging deeply with fellow pilgrims.

This format creates a perfect balance between solitude and community. You’re never truly alone (unless you choose to be), yet you’re free from group schedules or mandatory sharing circles. Connections form organically over shared meals or chance encounters on the path, often resulting in more authentic exchanges than facilitated groups can provide.

As Janet, a 58-year-old retreat participant, shared: “I’ve done guided retreats where I felt pressure to have the ‘right’ insights or experiences. On the Camino, I could be completely honest with myself. Some days were profound, others I just counted birds or worried about my blisters. Both were exactly what I needed.”

Practical Aspects of Legacy Building

The magic of walking retreats isn’t just in the experience itself but in how the insights continue to unfold and integrate after you return home.

Many participants find that decisions that seemed complicated before their journey now appear straightforward. The spaciousness of the walking mind often cuts through unnecessary complexity, revealing what truly matters.

I encourage participants to develop practices for preserving and implementing their insights:

• Journal during the journey without judgment or analysis
• Create symbolic reminders of key realisations (many find the traditional scallop shell serves this purpose)
• Schedule regular “mini-retreats” (even an hour of walking) to revisit Camino insights
• Identify one concrete change to implement immediately upon returning home
• Find ways to share your experience without diluting it through oversimplification

The most powerful legacy-building happens when Camino insights influence everyday decisions. As one participant put it: “I now ask myself before any major commitment: ‘Will this matter in my life story? Does it align with what I discovered on the Camino?'”

This regular return to deeper purpose creates a life of greater coherence and satisfaction. Small choices align with big values. The “noise” of urgent but unimportant demands diminishes. Space opens for what truly matters.

MyTransformational Camino Walking Retreats

The southwest France Camino experience I offer combines ancient tradition with modern comfort. Over seven days, you’ll walk the historic pilgrim route through golden countryside and medieval villages, staying in a comfortable farmhouse that balances authenticity with comfort.

This retreat is designed specifically for you if you are seeking deeper life reflection through the time-tested method of walking. Whether you’re contemplating career transitions, evolving relationships, or your broader legacy, the Camino provides the perfect container for meaningful reflection.

Participants describe the experience as “life-altering,” “clarifying,” and “exactly what I didn’t know I needed.” Many return year after year, creating an annual tradition of meaningful contemplation.

Whether you’re walking alone, with a partner, or with friends, the journey adapts to your needs. Many find that even when starting with companions, the path creates natural opportunities for both connection and solitude.

Frequently Asked Questions

How physically demanding is the retreat?

The route involves walking approximately 10-28 km daily over varying terrain. While not technically difficult, it requires basic fitness to walk for several hours each day. I recommend a simple training program in the months before your journey, gradually building to 3-hour walks. Remember, this isn’t a race—many find that slower walking enhances contemplation.

What if I’ve never done anything like this before?

First-time pilgrims often have the most profound experiences precisely because everything is new. The Camino community is famously welcoming to newcomers, and the route is well-marked. Many participants report that the journey helped them discover capacities they didn’t know they possessed.

How do you balance solitude with community on a non-guided retreat?

The beauty of the Camino is its natural rhythm of solitude and connection. Most walks begin with quiet walking, allowing for personal reflection. Shared meals and create organic opportunities for meaningful exchange with fellow pilgrims when desired. You’ll find a remarkable lack of small talk—something about the journey encourages authentic communication.

What kinds of insights or changes can I expect?

While every journey is unique, common themes include: clarified priorities, recognition of deferred dreams, new perspective on relationships, reduced attachment to status or possessions, and a deeper sense of life purpose. Many report continued unfolding of insights for months after returning home. The journey tends to answer the questions you need addressed, even if they’re not the ones you thought you were asking.

How does this compare to other retreat experiences?

Unlike meditation retreats that require sitting still, walking retreats engage the body in movement—often making contemplation more accessible for those who find traditional meditation challenging. Unlike adventure travel, the focus remains on inner exploration rather than external experiences. The combination of physical journey and inner reflection creates a uniquely powerful container for transformation.

Further Reading and Resources

For those interested in exploring the concepts of walking pilgrimage and legacy contemplation further:

• “Walking to Listen” by Andrew Forsthoefel
• “The Art of Pilgrimage” by Phil Cousineau
• “What Do You Want To Do Before You Die?” by The Buried Life
• “From Age-ing to Sage-ing” by Zalman Schachter-Shalomi
• “Walking: One Step at a Time” by Erling Kagge

The Call of the Camino

As our lives grow increasingly complex and digitally mediated, the simplicity of walking an ancient path offers a powerful antidote. The Camino de Santiago has been calling pilgrims for over a thousand years—each seeking answers to life’s fundamental questions.

What questions are you carrying? What aspects of your life’s direction would benefit from the clarity that comes from walking and reflecting? What legacy are you creating, intentionally or by default?

These questions deserve more than fleeting consideration between meetings or in late-night moments of restlessness. They deserve the spaciousness that only dedicated time away can provide.

My walking retreats offer this gift of time—seven days to contemplate what truly matters, supported by the wisdom of an ancient tradition and the beauty of the southwest French countryside.

To learn more about upcoming retreat dates or to reserve your place on this transformative journey, click here. Early registration is recommended as group sizes are intentionally kept small to preserve the contemplative nature of the experience.

Your future self—and those whose lives you touch—will thank you for this investment in clarity, purpose, and legacy.