Eight days walking in Portugal — to step back, hear yourself, and choose what comes next.
Join the WaitlistSmall group · One departure
Children growing up.
Careers evolving or no longer fitting in the same way.
Parents needing more.
Or simply a sense that something is changing.
And with that, a different kind of question emerges:
What matters most to me now?
How do I want to spend my time?
What do I want this next chapter to look like?
Not by default — but by design.
And possibly — the most interesting chapter yet.
You didn't build your life by accident. You made choices, worked hard, and created something real.
And now this chapter asks something different — not because you're starting over, but because what carried you here won't necessarily carry you forward.
On your own terms
Why this retreat exists
Because there comes a point when simply keeping everything moving is no longer enough — when the question shifts from how do I do more, to what I actually want.
Clarity rarely comes from pushing harder. It comes when you create enough distance to hear yourself again.
Beautiful, unhurried Portugal
Slow enough to think clearly
Small group, right fit
Conversations that go deeper than expected
Not a fixed plan.
But the beginning of one.
A note from Jane
In 2010 I left my employee job to become a contractor. I was done with the politics, done with career paths that didn't interest me, done with the slow grind of other people's agendas. I wanted out — and contracting felt like freedom.
For the first two years, I worked more hours than I ever had as an employee.
It wasn't until my boys were growing up that I felt it — that specific lump in the throat that tells you something matters.
I'd been searching for summer camps for them. Wonderful outdoor ones, a world away from hockey arenas. And realized, somewhere in the scrolling, that I didn't want to drop them off.
I wanted those summers with them.
So we started looking. We researched regions, compared tent trailers, scrolled through vacation rentals, and eventually wandered into properties for sale. That's when we found a cabin on Lake Okanagan. The kind of place that makes the decision for you. We bought it before I had a plan. Before I'd asked anyone's permission. In an industry where two consecutive weeks off was considered career limiting. I had just purchased a summer.
What pushed me over the edge was a conversation with a fellow contractor. She was taking the whole summer off. 'I have horses,' she said, as if it were the most obvious thing in the world.
I have kids.
I asked my boss. A long pause. Then, carefully: 'Will you come back in the fall?'
What I hadn't understood until that moment was simple: as a contractor, my value was in what I delivered, not when I showed up. The project was winding down. Starting the next one in September rather than June wasn't a problem — it was just a conversation I'd never thought to have.
The choice had always been there — I just hadn't recognized it.
We kept that cabin for fourteen years. Fourteen summers on the lake with my boys. It was the best thing we ever did for our family — and none of it would have happened if someone hadn't shown me, casually and without fanfare, that a different choice was simply an option.
I had the power all along.
Like Dorothy and her ruby slippers.
That's what I hope this retreat does for you.
This story is why this retreat exists. If it resonated — you're exactly who it's for.
Join the WaitlistThe team
This retreat is a collaboration between two people who each bring something essential — one designs what happens inside, the other designs everything that moves.
Retreat Founder · Program Director
For more than twenty years, Jane has helped business owners and leadership teams step back, ask better questions, and find clarity when navigating change.
Over the course of the journey, Jane creates gentle moments of reflection — a question shared over breakfast, a thought offered on the private shuttle between landscapes. Nothing formal. Nothing required. Just the kind of prompt that gives a good conversation somewhere meaningful to go.
Clarity & Change
Twenty years of sitting with people at crossroads — asking the questions that cut through the noise and listening carefully to what surfaces.
Twenty-plus years in the room
Since 2014 Jane has designed and led retreats for women entrepreneurs and leadership teams. She knows how to create the kind of room where people surprise themselves.
Founder, Qmooniti Travel · In-Country Lead
Based in Vancouver and traveling with us in Portugal, Lystra designs and leads the entire travel experience — coordinating accommodations, routes, transfers, and local hosts with calm precision.
Through Qmooniti, she curates travel grounded in cultural reciprocity and respect — ensuring every encounter honours place, supports the local economy, and reflects the living culture of Portugal.
Immersive travel design
Every stay, every host, every experience is chosen to honour Portugal as it actually lives — seamlessly designed, deeply connected to place, and grounded in genuine respect for the communities and culture we move through.
On-the-ground presence
Lystra isn't managing this from a distance. She travels with you — calm, experienced, and there for every moment of the journey.
You bring yourself. We take care of the rest.
Between us, you are held from both directions — the inner journey and the outer one.
There's something about walking that loosens things.
Without the pressure of eye contact, without distractions, ideas surface more honestly — and what matters most becomes clearer than it does at a desk or in a meeting room.
In conversation with other women who are asking the same kinds of questions, you begin to see your own life differently.
This is where clarity begins.
And sometimes, the answer arrives halfway through a conversation you didn't expect to have.
What makes this different
Most retreats give you space to breathe. This one gives you that — and something more.
Each day has a lens — a simple, practical prompt drawn from twenty years of helping people think clearly about what matters. Shared briefly in the morning. Explored over kilometres of Portuguese landscape. And at the end of the day, over a relaxed dinner, there's space to share what struck you — no pressure, just good conversation among women who've been thinking about the same things.
The tools are practical, not therapeutic. The conversations are real, not required. And what you produce alongside other thoughtful women is something you simply couldn't have built alone.
Think of it as a personal happiness plan.
Built by you. Shaped by Portugal.
What eight days looks like
The journey begins before you board a plane. We'll gather — virtually or in person — in the weeks before departure for a first introduction: to each other, to the places we'll walk, and to the thinking tools we'll use along the way. By the time you land in Lisbon, you'll already know the women you'll be walking with.
Mornings belong to you — coffee, a quiet start, the day's lens shared simply over breakfast. No agenda until you're ready for one.
Guided walks through Portugal's landscape — side by side, without the pressure of eye contact. Ideas surface. Conversations deepen. By mid-afternoon, you're thinking about things you didn't know you needed to think about.
Unhurried meals, good wine, conversations that help you hear yourself again. The kind of evenings you don't want to end.
· Two places to truly settle in
You'll stay in two carefully chosen locations — so you can arrive, exhale, and feel at ease rather than constantly moving on. Each place has been selected for its atmosphere, its access to walking, and its ability to make you feel held.
· Walking that creates space to think
Five days of guided walking — not for performance, but for the kind of rhythm where clarity begins to emerge. Something about it allows you to arrive at answers you didn't know you had.
· The kind of moments you don't plan
Some evenings unfold at our hotel base — seasonal meals, regional wines, and time to linger at the table. At times, a private chef prepares dinner; on others, we venture out to local restaurants where Portugal reveals itself slowly. Along the way, cultural encounters are woven into the days — with local makers, historians, and guides who bring each place to life.
· Everything taken care of — so you don't have to carry it all
Every detail is taken care of — meals, logistics, transfers, and planning. So for once, you don't have to hold it all together. You can simply arrive, and be looked after.
"All of a sudden I felt open and ready — removed from my usual environment, in this calm space with good food and good company."
— Joan W., Retreat Participant
Structured, but not rigid. This is not a tour with a fixed agenda. Some mornings are slower. Some days unfold differently than expected — and that's part of it.
The structure is there to support you, not constrain you. What matters is that you leave having had the experience that was right for you.
Something shifted here over time. The pace slowed, the focus turned inward, and a different rhythm took hold — slower, more grounded, more present.
We begin in Lisbon — a city that holds centuries of history lightly, where ancient and everyday exist side by side. From here we walk deeper into the country, and deeper into ourselves.
In many ways, Portugal mirrors the transition you're in. A life once shaped by striving, now asking different questions. This is the right place to consider them.
What becomes possible
Three things that quietly return when women finally give themselves space to pause.
Clarity
The kind that comes when you step outside the noise. What matters becomes simpler — and often, more obvious than you expected.
Energy
From being in a place that restores something in you. The kind of energy that comes from feeling lighter, freer, and fully present.
Permission
To choose what brings meaning, satisfaction, and joy — without needing to justify it to anyone, including yourself.
And somewhere in that space, you begin to remember what feels like you.
This is what eight days in Portugal makes possible.
What becomes possible
You return with something to carry into what comes next.
A genuine understanding of what brings you meaning, satisfaction, and joy — not as an abstract idea, but as something you can name.
A clearer sense of which possibilities truly fit who you are now — not who you were, or who others need you to be.
The confidence that comes from having listened to yourself, deeply and without distraction, for eight whole days.
Clear priorities and concrete next steps — not rigid, but real. A framework that feels genuinely yours, built over eight days in Portugal.
Women who do this kind of work together don't easily lose each other. After Portugal, the group stays connected in a shared space — so the clarity, the friendships, and the conversations can continue.
A set of simple frameworks and your own notes from eight days of thinking — a personal record of what surfaced, what shifted, and what you want to carry forward.
From women who've been in the room
Jane asks really, really good questions. It really made me dig deep and think about a lot of things — things that hadn't even crossed my mind, or that I hadn't been putting enough emphasis on. I found it really useful.
"Jane's facilitation style is wonderfully well-planned — and she brings a lovely sense of humour and attention to detail into every aspect of her work. We love working with her."
"The sense of community was the most powerful part for me. Being with other women who understood what I was experiencing made everything feel less overwhelming, and I left feeling more confident and clearer about what comes next."
"Being part of this experience reminded me I wasn't alone. The connection with other women, the perspective I gained, and the confidence I left with made it deeply meaningful."
This is the first time Jane is offering this retreat format — walking, reflecting, and planning in Portugal. The women who join will be the founding group. If what you've read here resonates, you're exactly who this is for.
Join the WaitlistEvery detail is taken care of. Private rooms, chef-prepared meals, local guides, and transfers throughout. This is not a trip you plan. It's one you surrender to.
Reserve My SpotNo obligation. No pressure. Just first access — and the chance to say yes before someone else does.
Join the waitlist
This is an intentionally small group. Full details, dates, and investment will be shared first with those on the waitlist. No obligation — just first access.
Join the WaitlistEarly inquiries welcomed · One departure
