This Year - JT’s Tales From The Trail, Sole Sister Ramblers

This Year - JT’s Tales From The Trail

If this year had a theme, it would be letting go — releasing pieces of my old life as I stepped into a new one, even though I didn’t yet understand what this next chapter would ask of me. It was my first full year of retirement, and while it held plenty of ease and joy, it also brought an unexpected reckoning with identity, change, and who I am and who I'm becoming now.

When I think back on this year, Bangkok rises to the surface first. I was there with my husband Stormy when the new year rang in, sleeping in a tiny apartment, Rambling and sweating through the heat, carrying a boatload of anxiety like a constant, ever-present companion. I’ve always known anxiety, but in the past few years, fueled by aging and difficult life events, it has started clinging to me with an intensity that is proving hard to shake.

I fell in love with Bangkok anyway. The Rambles there were electric. Alive. Colorful. Otherworldly. I loved soaking in the chaos. Being in the center of the universe rather than in the bucolic hinterlands I usually occupy was thrilling. Bangkok’s outrageous energy softened something in me, and as I Rambled, I could feel my anxiety loosening its grip, just a little.

In Bangkok, retirement began to feel like a celebration — what a joy it was to wake up each day and do whatever I wanted, in a city where one might see something astonishing every single day for the rest of one's life. Stormy and I eased into a daily routine that felt simple and good. I used to think routines were boring, but in Bangkok I learned there is a quiet joy in doing the same things every day — as long as you get to choose them.

This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers

Stormy and I stopped tracking the days of the week. In February, when our visa expired, we rode a train to Penang, Malaysia, where we spent two weeks celebrating Chinese New Year. On our return to Thailand, the border agent asked me, “What day is it today?” and I panicked, thinking it was some kind of sobriety test, and I had a one-in-seven chance of guessing correctly. I was so relieved when, after admitting I didn’t know, the agent smiled and said, “It’s your birthday!”

I was excited because we were meeting up with the Wades (our best friends) for a two-month travel adventure - first stop, Ko Lanta and the beach! Those months were a joy-filled stretch of time — unhurried, meandering, and rich with inside jokes and stories. What a delight it was to embrace an oddball itinerary and have so much unhurried time to simply be together - all doing exactly what we wanted to do every day.

However, alongside the joy walked anxiety, now stoked by a simmering lack of ease about being retired. I anxiously ruminated about never earning more money or saving up for something again - what a baffling notion. It was deeply unsettling. I found myself ruminating on the math and constantly reassuring myself that we will have enough. 

For months, I scrutinized every dollar, which made me feel constrained and like joy was something I had to justify. Stormy and I had deep conversations on Thai beaches about our changing lives and what it all meant.

And then, in the middle of all that tension, I realized I don’t want to stop working. I was having nightmares about sitting with my computer pretending to work while hiding from having nothing to do. I realized I don’t ever want a life of leisure filled with puzzles, pickleball, and card games … though I once swore I’d never outgrow heavy metal music, and yet that still happened.

But for now, I want to work — but way less than before. I want a slower kind of hustle so I can wake up and do what I want to do every day.

So I decided to truly lean into Sole Sister Ramblers, to let go of my fears of both failure and success, and see where this path might lead. That realization didn’t erase my anxiety, but it gave it context — and somehow, that made it easier to carry.

After the beach, we headed back to Bangkok, and Stormy and I were settling into this new life and feeling content and occasionally happy. I spent most of my days working, and together we spent our evenings exploring. We were starting to love the rhythm of our new life.

I realized in Thailand that anxiety doesn’t just disappear on its own —you can't just wait it out and hope it floats away. Releasing anxiety requires focused attention, gentleness, and effort. You have to look it in the face and decide to start doing the work. I made this commitment in Thailand with morning walks, journaling, and podcasts, and day by day, the anxiety lessened.

This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers

Our Asian adventure came to a close in the spring, but hosting our first Sole Sister Ramblers travel experience on the Camino in Spain had me back on a plane just three weeks after returning home. Walking the Camino had long been a dream of mine, and beginning that journey on a guided trip with our Sole Sister community felt like a safe and meaningful way to start.

It was a watershed moment in many ways — both personally and for Sole Sister Ramblers. It marked how much this community has grown, how meaningful it is, and how hard the five of us founders had worked to get here. It was a reminder of just how extraordinary that journey has been. It’s hard to fully describe how good it felt to walk that ancient trail with women from around the world, and to know that if it weren’t for my friends and me, none of us would have been there at all.

I crossed the Camino finish line in Santiago de Compostela, wiping tears from my eyes, surprised by how close our group became in such a short time, and by how emotional the moment felt. I was also stunned that I had walked 100 kilometers in six days. It felt both impossible and completely right.

This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers

Three weeks later, I crossed that same finish line again. I had decided to walk the Portuguese Camino from Porto to Compostela de Santiago, starting a week after finishing my first Camino. I hoped walking alone would be balm for my inner restlessness, perhaps banishing it to the wilderness once and for all.

I arrived in Porto, Portugal, forty-eight hours after I had said goodbye to my Sole Sisters in Spain, with a fresh batch of anxiety in full bloom. I was fiercely ruminating about the prospect of walking more than twice as far without a supportive bubble of Sole Sisters, luggage transfer, and pre-booked hotels. I was also worried about the weight of my backpack and was confident that sleeping in hostel bunk beds would be miserable. I was, however, most anxious about traveling alone—something I have not done in thirty years.

Burdened by these worries, what I wanted most was to go home and cuddle my cat. I kept asking myself why I needed to do this. The answer was clear - this is the kind of thing I love to do, and that I needed to find the side of me that is capable and brave again.

Serendipity—and a bit of peer pressure—brought my good friends and fellow Sole Sister founders, Jane and Naomi, to Porto while I was there, so I stayed a few extra days. Jane walked the first 15 km of the Camino route with me as a practice run, then gifted me her favourite bucket hat. The following day, Naomi, Jane, and I explored Porto together and shared a beautiful dinner. I felt wrapped in love—and deeply grateful.

Early the next morning, I set out alone and almost immediately broke down in tears — something I would soon discover would become a familiar pattern on this journey. I had vowed to walk alone, to spend my days in solitude and contemplation. But on my first day, I met Daniella, my wise Italian Camino buddy — what an incredible stroke of luck.

This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers

I quickly came to understand that a pilgrimage is, at its core, a communal experience. When you walk with others day after day, kilometer after kilometer, sharing a common purpose and facing small challenges together, shallow conversations naturally deepen into a real connection. I learned how easily belonging can emerge when you simply keep walking alongside others.

A few days later, I met Dorn and Sage, and we became a little family as the miles clicked by. When we crossed that finish line in Cathedral Square, the feeling was indescribable. I can’t think about it today without tearing up.

All of us were walking with something heavy — grief, uncertainty, unspoken struggles. And like so many pilgrims before us, we learned that the Camino can knit broken things back together. For the first time in three years — maybe ever — my anxiety disappeared completely, all day, every day, for days at a time. It was intoxicating.

This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers

I headed home to Salt Spring Island, British Columbia, as spring tipped into summer, determined to re-learn my hometown again. I spent three slow months digging in the garden, cocooned in my outdoor bed with my cat, the owls, and the argumentative geese.

What a lovely surprise it was to have our son Jacob home for the entire summer before he left for China to teach. Sharing space again — meals at odd hours, conversations with nowhere to be — is a rare kind of time with an adult child. I also reconnected with my local Sole Sisters and made a new walking friend in my neighbor, Joyce.

Late fall brought me back to Toronto— a second home, and a city filled with friendships that changed my life when I was a teenager. I Rambled through much-changed yet forever familiar city streets and spent long, leisurely hours reconnecting with dear friends. 

I was there for our annual Sole Sisters planning meeting — Naomi and Jill live there, Tara traveled in from Chicago, and Jane came from Spain. Jill, Naomi, Tara, and I all grew up in Toronto, but it was Jane’s first visit. She was patient as we Rambled her down memory lane for miles upon miles through all our favorite urban haunts.

Spending a week at Naomi’s cottage was a highlight — a deep exhale. The late-fall colors — yellow and red leaves on the deciduous trees set against the deep green boughs of the white pines and the crisp, navy-blue lake — were astoundingly stunning. Having that time alone with Naomi — just the two of us — was rare, peaceful, and grounding.

We fell into a quiet rhythm: coffee, quiet work, late-afternoon canoe paddles, cold dips I never thought I’d tolerate (and somehow came to enjoy), and drinks on the dock while her dog Odin proudly ferried rocks from the lake to her garden like a joyful lunatic.

This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers

Stormy and I flew back to Thailand as fall was turning into winter. While he continued on to Chiang Mai, I spent a week in Bangkok with my friend Cheryl, arriving in the city before dawn. Unable to check in yet, we dropped our bags and headed straight to Benjakitti Park — one of my favorite places in the city.

From there, we Rambled, sleepless but buoyed by novelty, through the old town, Chinatown, and on to Khao San Road, eventually riding the BTS back to the throbbing heartbeat of Asok Station. We checked into our hotel at 3 p.m. and collapsed onto our pillows like Garfield into a pan of lasagna. Awake again at 4 a.m. we took a tuk-tuk to the bustling wholesale flower market where Cheryl tasted her first Kra Pow Gai before we watched the sun rise over the Chao Phraya River.

Cheryl and I talked a lot about being aligned in Bangkok — about how, if you do the work, and you're lucky, there might come a time in life when who you think you are, how you act, and who you truly are begin to align. We talked about getting a straight line tattooed on our arms (and I hope we do someday). We noticed lines everywhere — in street art, in laneways, in temples, and in the horizons of our photographs.

This Year - JT’s Tales From The Trail, Sole Sister RamblersThis Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers

Shortly after Cheryl flew home, I flew to Hanoi to spend time with Tara before she hosted our Sole Sister Vietnam travel adventure. The timing felt especially meaningful — her daughter Zoe was in town, wrapping up two years in the Peace Corps.

Spending time with Zoe and her tight-knit gang of Peace Corps friends, all of whom were basking in the well-earned pride of a serious accomplishment and preparing to step back into the “real” world, brought me to tears. I could feel how much they loved each other, how this experience had bonded them. They were so kind to one another, and it made me feel incredibly hopeful.

Vietnam is one of Tara’s happy places, and we Rambled marathons as she guided me through every corner of Hanoi's Old Quarter, introducing me to the best street food and elaborate coffee drinks. Whenever we needed to cross one of Hanoi’s infamously busy roads, I’d tuck in behind her like a baby chick, waiting for the flick of her hand that meant let's go now. If I hesitated, she’d loop her fingers around my wrist and pull me through the sea of motorcycles. We had three massages and circled Hoan Kiem Lake every morning and evening. The waitress at our favorite beer spot had our order memorized.

On my last night in town, I crashed the first-night dinner with Tara and the other women embarking on our first Sole Sister Vietnam travel adventure. I had so much fun with this gregarious, hilarious group of women. They were all buzzing with excitement, standing on the brink of an adventure of a lifetime — and later, Tara and I were giggly with joy when we said our goodbyes.

This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers
This Year - JT’s Tales From The Trail, Sole Sister Ramblers

One of the best things about this stage of life — as my hectic life winds down — is having more time for friends. Slow, unhurried, thoughtful time. The kind I hadn’t really known since high school. It makes me feel like the luckiest person on earth.

And today, as I write this from a hotel room in Chiang Mai, just hours from another new year, I feel calm and content. All is well in my world — so much better than this time last year. I’m proud of the work I’ve done, and deeply relieved.

But still, there are moments — hard ones — when the anxiety slips back in, bringing with it ruminations on everything I’ve already lost and all that I will likely yet lose as I (God willing) continue on into old age. I understand now what people mean when they say aging is not for the faint of heart. The joy and the grief of this season of life arrive intertwined, in a way that cuts deep.

What this year has taught me, as I let go of one life while building another anew, is that my anxiety is a signal, something asking to be listened to. And that I have tools I can rely on when needed.

This year wasn’t neat or easy, but it was fun. It was a year of becoming — of shedding, grieving, recalibrating, and remembering who I am when I’m not afraid.

READ MORE > JT'S Tales From the Trail


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