On Belonging: Why I Built a Travel Company for Women in Midlife

By the time I was sixteen, I was paying rent.

I worked. I cooked for myself. I let myself into a quiet house most nights, where another family lived. People who had taken me in. People who were kind to me. People who were not quite mine, and I was not quite theirs.

If you have ever lived in that in between, you know the shape of it. Not unwanted. Not unloved. But not quite belonging anywhere either.

For most of my younger years, I carried a quiet question with me. Where do I actually fit. Whose person am I. It was not loud. It was not dramatic. It just sat there, in the background of my life, the way some questions do when there is no clean answer.

I tell you this because it is the beginning of why Grit & Grace Adventures exists. Not the polished founder story. The real one.

Travel was the first place I felt like myself

The first time I really left, I felt something I had not felt before.

Nobody on a train in a country that was not mine knew where I had come from. Nobody knew that the family I lived with were not my family. Nobody knew the rent I paid at sixteen, or the long years of being polite in a house that was kind but not quite home.

In a place where nobody knew me, I could finally find out who I was without all of that.

That is not what I expected travel to give me. I went looking for adventure. I came back with myself.

Years later, I lived in the Okavango Delta in Botswana. Days that began with the sound of hippos and ended under stars I had never seen at home. I felt like myself out there, properly, for what might have been the first time. I thought that meant the work was finished.

It was not.

I came home. I went back into corporate. I told myself I had grown enough to hold the shape of an ordinary life. Within months, I was back inside old patterns I thought I had outgrown. Quietly performing. Quietly shrinking. Quietly forgetting what I had remembered out there.

The environment had won, the way environments do.

So I left a second time. To a tiny casita in the Costa Rican jungle, where the only company I had was the howler monkeys, the morning light, and my own thoughts. I stayed two years. I did not date. I did not perform. I walked. I journaled. I sat with myself long enough to actually hear what I had been drowning out.

That second leaving is when I understood something the first one had only hinted at. Belonging is not a place you arrive at once and stay. It is a thing you keep choosing, in different forms, at different ages, against the steady gravitational pull of every old environment that wants you back as you were.

I had to leave the same problem twice before I understood that. Most of us do.

What I notice in the women who travel with us

I see something now, sitting across the table from the women who travel with Grit & Grace Adventures.

Most of them are not running from anything dramatic. They are not in crisis. They are in their late forties, fifties, or early sixties. The children are grown or close to it. The career is steady, or winding down, or quietly being rebuilt. From the outside, life is sorted.

And yet.

By day two of a journey, when the wine has loosened the day a little, the same thing keeps coming up around the table. I am not entirely sure who I am anymore. I have been so many things to so many people, and somewhere along the way, I lost track of who I am when none of them need me.

What these women are describing is not a midlife crisis. It is a midlife belonging question.

The same one I carried as a teenager. Just from a different angle.

At sixteen, I did not know whose person I was. At fifty-something, many of the women I travel with do not know whose person they are without their roles. The mother. The wife. The manager. The reliable one. The woman who held everything together for everyone else, for decades, until somewhere along the way, she went quiet.

Why belonging gets harder in midlife, not easier

Belonging in midlife is a quieter, sneakier question than the one I carried as a girl.

In your twenties and thirties, the world hands you ready-made answers. You belong to a job. You belong to a young family. You belong to a hundred small obligations that fill every hour. There is not much space to ask whether any of it actually fits.

Then the children grow up, or they move out, or they simply need you less. The career either steadies or starts to soften. The marriage matures into something different. The roles that have been answering the belonging question on your behalf, quietly, for thirty years, start letting go of you one by one.

And in the space they leave behind, the question comes back. Where do I belong now? Whose am I? Who am I when I am not needed?

It is a beautiful question and a brutal one. Most women I know do not get to sit with it properly because life is still loud. The aging parents. The grown children with their own crises. The home that still needs running. The sheer momentum of a life that has been built around being available.

That is part of why women travel with us. Travel is one of the few things you can do as a grown woman with responsibilities that legitimately require you to be unavailable for a stretch of time. The phone goes quiet. The diary clears. The roles step back, just for a while.

Travel does not give you a new self. It returns you to the one underneath

I want to be honest about what travel can and cannot do.

It cannot solve the belonging question. No country, no journey, no woman around the dinner table can hand you the answer. The work is yours. It will always be yours.

But travel can do something almost as useful. It removes you from the environment that has been answering the question for you. And in that quiet, the woman you have been quietly carrying around for decades, the one who never quite got to come out, finally has space to take up.

She is not a holiday version of you. She is the underneath version. The one your home, your family, and your routine have been gently editing for a long time without anyone meaning to.

When you spend a week or ten days with women who do not need anything from you, in a place that has no script for you, she comes forward. Sometimes shyly. Sometimes all at once.

And then, if you are lucky and you pay attention, you bring some of her home with you.

That is the work of belonging. Not finding a family that fits. Becoming the woman who fits her own life.

Why I lead these journeys

I built Grit & Grace Adventures for the women I keep meeting. The ones who are quietly asking where they belong now. The ones who have given so much of themselves for so long that they are not entirely sure what is left when they stop giving.

I built it for women like me, who carried a belonging question for too many years on their own.

I built it because the answer, for me, was never one place or one family. It was the steady accumulation of moments where I got to be fully myself. Around a table in Italy. On a road in Botswana. With women who knew nothing of my old story and asked me, kindly, who I was today.

Belonging, it turns out, is not somewhere you arrive. It is something you practice.

These journeys are an invitation to practice it.

For the woman quietly asking the question. For the woman who has been everything to everyone. For the woman who has spent decades being reliable and is ready, finally, to be free.

You do not have to know yet what the answer is.

You just have to be willing to start asking out loud.

xo

Penny