Ticket for a Different Hike. Ticket for a Different Life.

What I learned from late-night conversations and a pivot on our planned hike

May 04, 2026

One of our daughters is visiting us this week, she and a friend, here in Madeira for the flower festival, the warmer weather, and a break from Chicago winters. On the first evening, we opened a bottle of wine and talked about life the way you do when everyone has finally stopped performing for each other.

We told her what parents say along the rocky path of life: how proud we are, how much we see her hard work, how she is building something real and learning to trust herself and her wings. She listened. She shared her own view of how life feels to her and how proud she is of herself, too.

I mentioned how sometimes friends here will ask us, “How can you leave your children?” And we always remind them that our children are indeed now adults and our role as parents has shifted; we are not wiping hineys anymore, but rather leading by example how to do hard things. We feel we are leading… not leaving. There is a difference.

Then she said something every parent wants to hear at some point, too.

“Thank you both”, she said.

And as a stepparent, this can be a nugget of gold to be included in this conversation. She then said something that surprised and affirmed our choice to take a flying leap into the unknown of full-time travel and this unconventional life we created. She said, “I am just so proud of you two. And in case no one has told you, I just need to say it. You walked away from everything, and that took real courage.”

I have been thinking about that moment ever since.

Because we spend so many years teaching our children to plan and prepare. Not just in their careers and life, but also when it comes to money and investing, which we talk about with our kids on each visit… now understanding the benefits of having this mindset early from our own research and careful planning in our own lives. Save early. Live on less than you make. Let compounding do the quiet work. Your fifty-year-old self will thank you. We believe all of it. We mean all of it. My husband and I still listen to retirement podcasts. I still make graphs.

But somewhere along the way, we also had to learn the other thing. The thing that cannot be graphed.

Mountain momma sheep with her baby on the drive to our planned hike, PR1. An image of the symbol of the article as parents, we try to teach and lead our children on the sometimes rocky paths and unexpected terrain of life.

As one podcast host put it, you cannot read the label from inside the bottle. And if we knew how this play called life would end, we might make different decisions today. But we don’t. So we plan, and then we plan some more, and sometimes, in the middle of all the planning, the universe suggests a different trail.

Shakespeare said all the world is a stage. I have been thinking about that too, sitting at cafes here in Madeira, watching the fog come down off the mountains. If he is right, then many of us have been performing for a very long time. And the question that keeps surfacing for me is: for whom?

The mask of the plan. The mask of the house. The mask of arrival.

We wear them so long we forget they are masks at all.

Most of our friends are at the hinge point now, selling the family home, moving somewhere warmer, building the next version of the life they already have. There is nothing wrong with that. There is real beauty in the predictable routine, in the satisfaction of having arrived.

Except for arrival, I have learned, it is a temporary state. The new car smell fades. The countertops, once luminous, become the surface that holds the keys and the mail and the fruit going soft. Things slot into function. Possessions become responsibilities. What once felt like freedom starts to feel like maintenance.

The day we closed on our house, we had two suitcases and two backpacks. Decades of accumulated life dispersed among our six children to furnish the early chapters of their own stories. We turned out of the driveway for the last time as owners, and I cried, and we laughed, and we grabbed each other’s hands and held a stare that was equal parts terror and something that felt, uncomfortably, like joy.

Then my husband said: We need a place to sleep tonight.

In that pause, phone in hand, searching for a hotel while he drove, something I had been wearing for years started to come loose. I had been so thoroughly planful. So thoroughly the woman with the next step mapped, the next decade considered. And here I was, no house, soon no car, no plan for the next twelve hours, booking a room from the passenger seat like a person who had just arrived in her own life for the first time.

It was disorienting. Underneath the disorientation, there was also a quiet relief I did not have words for yet.

That is the thing about the mask. You don’t know how heavy it was until you take it off.

And our children watched us take it off. They watched us do the thing we never explicitly taught them. They watched us not know, and go anyway.

I had spent weeks monitoring the new online booking site for the PR1-Vereda do Areeiro - Pico Ruivo hike, the newly reopened full mountain hike that draws hikers from all over the world. I finally got an afternoon slot. I had a plan.

We started our trek up the mountain pass to the top of the peak to start this hike. I had only hiked part of this trail before fires in 2024 closed the second half of the hike that led to the other peak, Pico Ruivo. This hike basically takes you from peak to peak of Madeira’s highest mountains. I had waited two years to hike the full hike, and this was opening weekend.

But the universe had other plans, as often happens in life.

The morning was clear on the mountain, but our tickets were for an afternoon start, and there would be no exceptions with this new booking system.

By afternoon, the mountains had disappeared entirely behind the islands, along with the famous and mystical clouds. We would have walked into a whiteboard of nothing.

On our arrival at the top, it was a whiteout.

This would not be the day we planned.

So we pivoted.

Our guide suggested the Caniçal Levada, the Larano Footpath, part of the newly opened GR1 that spans the island like beads on a string. I had never walked it before.

We were all in agreement to drive to another hike that did not need advanced notice (there are many on the island). We planned for one thing, but there was something else we needed to experience that day, it seemed. I have learned to trust that when it happens.

We drove toward the coast, away from the clouds, and started down a different trail we seemed to have entirely to ourselves.

It began gently, following a levada past small farms and local houses, sheep and goats, a garden of beans and squash and bananas too small and too sweet to find anywhere else. Then it turned into a wooded trail as we headed into the mountain’s interior. Lush green moss covered rocks and groundcover blanketed the side of the mountain.

Then it turned upward. We climbed the rocky face of the mountain, and I started to feel like the goats we had passed weaving up this new and unplanned path. My layers came off one by one. My backpack, stuffed for the wrong hike, was overstuffed and ridiculous and also fine.

My hiking partners for the day’s adventures

We emerged onto a ridge facing the sea. Two women sat on a boulder above the cliff, legs dangling, eating a picnic. GR1 walkers moved past us carrying what looked like their whole lives on their backs, faces settled and inward, already somewhere else.

We ate peanut butter and jelly sandwiches above the bay of Porto da Cruz in the particular silence that only arrives in beautiful places. The kind that is not absence but fullness.

We ended the hike in the coastal town at a local bar with poncha- a local citrus, rum, and honey drink, and the knowledge that the body had been well used. It tasted like an elixir. It tasted, if I am being honest, like what it feels like to stop arguing with what is.

The end of this hike takes you to the coastal village of Ponta da Cruz.

The hike was more beautiful than I had imagined. I experienced a new side of the island and found peace without the crowds of the more popular hike. This was not the hike I had planned. It was not what I expected. It was exactly what I needed, which I had not known to ask for.

This is the thing I keep returning to.

We plan because we must. But we also plan because we are afraid of being untethered, afraid of the version of ourselves who does not have a script, who might say I don’t know, let’s see and mean it without panic.

The mask of the plan is the most socially acceptable mask there is. No one questions the woman with the spreadsheet.

But life is, at its core, an improvisation. The best things that have happened to me in the last two years arrived through pivots I did not choose, through tickets purchased for one experience that became doors to another, if I was willing, just willing enough, to walk through.

The untethering I thought was about the house and the car and the stuff has turned out to be about something far more interior. The only safe harbor, I am learning, is the one that moves with you. Everything else is beautiful, and temporary, and not the point.

We can tell our children to save and invest, to let the money compound. We can tell them to build something real and meaningful in their lives and live on less than they make. To be good stewards of the gifts they have. All of that is true and worth saying.

But what we cannot tell them — what can only be shown — is what it looks like to hear the voice underneath the plan and actually follow it. To drive past the trailhead of the life you scripted and take the one the morning offered instead.

A portion of the GR1 trail we hiked today instead

Our daughter raised her glass and said she was proud of us, and I understood in that moment that we had taught her something we never set out to teach. Not from a podcast. Not from a graph.

From a driveway in March. From a different trail. From two suitcases and a stare.

The work of the second season is not acquiring the right new life. It is learning to hear the voice that was always there underneath the planning. The one that says: “ This trail, not that one. Not because it was scheduled, but because something in you already knows.

That voice is not loud. It is also never wrong.

The Midlife Nomad

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