Chasing Dreams

The journey began long before I stepped onto the trail.

It started in my driveway, when my family drove me to the airport.

I didn’t think I would cry, but suddenly there I was — hugging everyone goodbye and apologizing.
“Sorry I’m missing track.”
“Sorry I’m missing your birthday.”

The guilt took hold for a moment.

Then I walked into the airport, saw the Air Canada sign, and excitement lit up in me. And just like that, it began.

Very quickly into the trip, I noticed something. Everywhere around me, people sat with their eyes locked onto their devices. Heads down. Scroll, scroll, scroll. Few conversations. Few people noticing each other.

So I made a quiet promise to myself: put the phone away and be present. Create connection.

Leaving Saskatoon, I met a family of four heading to Portugal to walk the Camino. We had different routes and destinations, but for a moment our journeys overlapped. The dad told me I looked prepared. I laughed and thought my situation was considerably easier since I hadn’t invited a spouse and children along for my hike.

In Toronto, I sat beside a Russian man who now lives in Canada and was travelling to visit his 92-year-old mother. She still lives alone, cooks for herself, and works. Ninety-two. I found myself wondering if her village is some sort of hidden Blue Zone.

As we talked, he shared how much his neighbourhood has changed over the last 30 years. More homelessness. Fewer connections. Fewer visits from people who once reached out often.
“Everyone is busy,” he said.

Busy.

It struck me that maybe “busy” has become the word we use when we don’t know how to say disconnected.

After a quiet pause, he boarded his flight to Istanbul.

My next conversation was with two women from Toronto who were complete strangers to each other, both headed to England. One was reuniting with her daughter and grandson, the other with her fiancé. We chatted about the meaning behind our trips, what they loved about England, and naturally… complained about Canadian winters. Weather really is universal conversation currency.

Before boarding my overnight flight to Lisbon, I wandered the terminal and met a woman heading on a Mediterranean cruise. Over the next 12 hours, we crossed paths several times and each time she greeted me with the same warm smile.

Then another connection.

A tall, slender woman was handing out books to travellers. Curious, I asked what they were. She explained she was escorting 24 people on a 16-day Portugal bus tour.

As we talked, I learned she had sold her business and retired early. Now, for fun, she travels Europe guiding groups of seniors — and gets paid to do it. Though apparently, the expectations of retired travellers can make her earn every penny.

Nearby, I spotted two women in their 60s carrying backpacks and immediately wondered about their hiking plans. As luck would have it, we ended up together in the boarding line. One had walked the Camino six years earlier and was back to do it again. That alone felt like a good sign.

The red-eye flight sounded better in theory than reality. I discovered airplane sleep does not compare to being horizontal in a bed — even for someone like me who naturally sleeps in corpse pose and is quite skilled at taking up very little space.

I spent my first night in Sacavém, a small community just outside Lisbon. My little apartment was simple but perfect — only two train stops from Oriente Station, home to stunning architecture, public art, and remnants of Expo ‘98 history.

That afternoon I tested both my navigation skills and perhaps my age. I managed the streets of Sacavém, bought a train ticket from an automated machine, and then stood staring at four different tracks trying to decipher where exactly I belonged.

I knew enough from travelling in Asia that not every train stops at every station, so uncertainty crept in. I finally pulled out my phone, typed into Google Translate:
“Hello. Can you help me?”

I handed it to a kind woman sitting nearby. She smiled and gently informed me I was standing on the wrong side of the tracks.

So I gathered my things, climbed the overpass stairs, crossed to the other platform, and settled onto a bench.

For a moment, I just sat there taking it all in. The artwork. The movement. The unfamiliar language. The realization that I was actually here.

I had to pinch myself a few times at the enormity of this adventure and the opportunity in front of me.

Eventually a train arrived. I hopped on and thankfully it was, in fact, heading the right direction.

I didn’t make it into downtown Lisbon. I missed the cathedrals and many of the postcard sights. But honestly, I gained something else instead.

I experienced what it feels like to not know the language. To navigate uncertainty. To rely on strangers. To trust myself. To begin.

Day one set the tone for this journey: my heart is full, connection is everywhere, and I require an 8 p.m. bedtime.

I slept deeply that night in Sacavém and woke up ready to finally begin walking.

I’m glad you’re here.

Until next time….there’s more to come.

XO