I left for Portugal on April 30th knowing I needed more than a vacation. I needed space to think, to walk, and to be reminded why the work I do matters. Ten days along Portugal's Fisherman's Trail gave me all of that, and then some.
The Rota Vicentina's Fisherman's Trail runs along one of Europe's last wild coastlines, from Porto Covo in the Alentejo south through the Algarve. It's a working route, used for centuries by fishermen navigating cliffs and coves long before it became a trekking path. There's something fitting about that history for an advocate — it's a trail built on persistence, on knowing the terrain, on getting to the people who need you.
Trek Epic designed this particular journey not just as a physical challenge but as a structured professional development experience, weaving the Core Gift Discovery Process through each day's facilitation sessions. The small group included coaches, counselors, and educators from across the country. By day three, the conversations happening on the trail were as rich as anything I've experienced in a conference room.
Day one in Lisbon, before the trail began
Where It Began
Lisbon, and the
slow shift
into presence
We gathered first in Lisbon, which is the kind of city that immediately asks something of you. The cobblestone streets climb in unexpected directions, the buildings are painted in terracotta and cream and faded rose, and nothing moves at the pace you arrived with. It's a city that rewards slowness.
That first day wandering Lisbon, I started doing something I rarely do at home: I stopped and just looked at things. The rainbow umbrellas stretched across an entire street in the Baixa neighborhood. A doorway that had probably been there for two hundred years. The way the late afternoon light hit the azulejo tiles on a corner building. I was already beginning to shift.
The Mermaid Retreat, Porto Covo
The harbor below the village
Porto Covo
White houses, blue trim, and the
start of something
Porto Covo is a small fishing village that looks exactly like Portugal is supposed to look. Traditional white houses with blue trim, cobbled streets, cats in doorways, and a harbor where a handful of working boats sit in water so green it seems artificial. We based ourselves at the Mermaid Retreat for the first two nights, gathering each evening under the reed-covered patio for group facilitation.
Those evening sessions introduced the Core Gift Discovery Process in a way that surprised me. We weren't being asked to complete a worksheet or follow a module. The facilitators created conditions for something more organic: real conversation about what each of us is genuinely built to do, and how our work reflects that. For me, the conversations kept circling back to families. To parents sitting across the table from a school district that holds all the information and most of the power. To the particular kind of advocacy that requires both a legal grounding and a deeply human presence.
Sunset over the Alentejo coast
The Trail
Walking as a
method of thinking
There's something that happens to your thinking when you walk eight or ten miles along a coastal trail. The noise that fills a normal workday — emails, case files, deadlines, the logistics of running a practice — gradually quiets. What's left is cleaner. You start to see patterns and connections that the daily pace doesn't leave room for.
I found myself thinking about the families I work with differently out there. The ones navigating IEP processes for the first time, who don't yet know what questions to ask or that they have the legal right to ask them. The ones who've been told their child's needs aren't severe enough, or that the program they're in is appropriate when it clearly isn't. Walking mile after mile with nothing but cliffs and ocean on one side and scrubland on the other, I kept coming back to the same thought: these families need someone who knows the terrain. That's the job.
The Fisherman's Trail coastline south of Vila Nova de Milfontes
The families I work with need someone who knows the terrain. Ten days on this trail reminded me how much that metaphor actually means.
— Maureen Brown, Ask the Advocate
The Atlantic from above
The Trek Epic crew, geared up and ready
The Group
What happens when
professionals slow down together
Trek Epic assembled a remarkable group. Coaches, therapists, educators — people who spend their professional lives holding space for others, and who rarely get that held for themselves. The van rides between trail sections became their own kind of facilitation. Someone would say something honest about what they were struggling with in their practice, and the conversation would open up in a way that a structured session sometimes can't.
One thing that came up repeatedly was the tension between expertise and connection. Most of us in helping professions have deep technical knowledge, and we've learned to lead with it. The Core Gift work pushed back on that gently but persistently. The gifts that make us most effective aren't usually the degrees or the certifications. They're the harder-to-name things: the capacity to sit with uncertainty, the ability to translate complexity for someone who's overwhelmed, the willingness to stay in a difficult room.
Crossing to the next section of trail by boat
The Work Behind the Walk
What I'm bringing
back to practice
True North, indeed
Professional development that actually changes something is rare. Most conferences give you information. This trip gave me something different: a clearer sense of what I'm doing and why it works when it works.
The Core Gift Discovery Process helped me name things I'd been operating from intuitively for years. My ability to translate the legal framework of IDEA into language a family can actually use. The way I approach an IEP meeting not as an adversary but as someone who's been in that room many times and knows how it moves. The fact that I can hold a family's fear and still stay focused on the strategy. These aren't just skills. They're gifts, and naming them matters because it shapes how I show up.
I'm bringing that clarity directly into client work. It's sharpening the way I open consultations, the way I frame what families can realistically expect, and the way I talk about the longer arc of an advocacy relationship. It's also informing how I think about the educational content I create — the posts, the community resources, the sessions I run — because all of it should reflect the same grounded warmth that makes the in-person work effective.
Lunch break somewhere between Almograve and Zambujeira do Mar
Nights on the Trail
Small villages,
honest meals,
and the spaces between
The villages along this section of coast are unhurried in the best possible way. Miramar in Porto Covo. A hostel in Zambujeira do Mar where two people spent a rainy evening working on a thousand-piece puzzle while the rest of us talked. The Bohemian Antique Guesthouse in Odeceixe, with its arched wooden door and stone surround, tucked into a village right at the border of the Algarve.
Those in-between hours mattered as much as the trail miles. Evenings around a long table, the kind of conversation that only happens when no one is in a hurry, the particular intimacy that comes from having shared a hard and beautiful day with a small group of people. It's the same dynamic I try to create in facilitation work — conditions where people can be genuinely honest, because the environment makes it safe to be.
Miramar, Porto Covo
Rainy evening at Hostel Nature, Zambujeira do Mar
Sines harbour
Evening facilitation, somewhere along the way
Odeceixe
The last stretch, and
what it means to arrive
The final days of the trail moved through Odeceixe, a village that sits right at the boundary between the Alentejo and the Algarve. It has a particular quality of light in the late afternoon, and the streets are quiet enough that you can hear your own thoughts. The Bohemian Antique Guesthouse felt like an appropriate place to land — there's something about a space that's been thoughtfully lived in that invites reflection.
I've done enough long trips to know that the insights from this kind of experience don't fully surface until you're home and back in the rhythm of ordinary life. But I came back from Portugal with something more concrete than I usually carry: a clearer articulation of what Ask the Advocate actually offers, and why it matters. Not just the legal knowledge, not just the years of experience, but the particular combination of warmth, precision, and persistence that the families I work with need most.
Bohemian Antique Guesthouse, Odeceixe
Coming Home
Ten days later, and
back to the work
I landed back in Massachusetts with sore feet, a full notebook, and more clarity than I left with. The advocacy work is the same — the IEP meetings, the legal timelines, the families trying to figure out what their child actually needs and how to get the school district to provide it. None of that changed while I was walking the coast of Portugal.
But I changed a little. I'm more deliberate now about the pace I set in consultations. I'm more intentional about making sure families understand not just the strategy but the reasoning behind it. And I'm more confident in something I've known for a long time but don't always say plainly: I've spent over twenty years learning this terrain so that families don't have to navigate it alone. That's the gift. That's the work.
If you're a family in Massachusetts trying to figure out what your child's IEP should actually look like, or whether the program they're in is genuinely appropriate, I'd be glad to talk. The first step is just a conversation.
