Finding Your People: A Story About Loneliness, Remote Work, and Belonging

Before we left for our sailing journey, I thought I understood loneliness. I thought loneliness meant not having people around you. I thought it was about distance and places and empty spaces.

I was wrong.

Our first loneliness showed up long before we ever set sail. It happened in the conversations we had with people we loved. Not because they didn't support us, but because they didn't really understand us anymore.

"You're so brave, I could never do that","Did you win the lottery?", "Are you sure?"

These were kind comments, but they carried something that surprised me. They made our decision sound extreme or unusual, something that belonged to people who were different from us. When in reality, we were just a regular family choosing a different rhythm.

And little by little, a small distance formed. Not a fight, not a conflict. Just a quiet shift. A feeling of being slightly misunderstood. A feeling of stepping into a life no one around us had lived before, which meant they couldn't really walk with us into it.

That was the first kind of loneliness. The one that shows up when your world starts changing and the people around you can't quite follow.

Loneliness Looks Different Than We Think

Once we left, we carried that feeling with us. We met people along the way. Families with boats. Kids to play with ours. Lovely conversations. Shared dinners. Moments that felt like the beginning of something.

But every time, everyone lifted anchor and continued on. And the moment dissolved as quickly as it appeared.

By the time we reached Grenada, the longing for a deeper connection had grown. The anchorage was full of families, full of kids, full of life. It looked perfect on the outside, but the rhythm didn't match ours. Not because of anyone's fault. Just because not every group fits every person.

Trying to belong where you don't naturally belong is its own kind of loneliness.

We tried to join in, hoped it would click, but sometimes, even when everything looks right, something inside you knows it isn't.

Eventually we lifted anchor and moved a little north. We simply needed a break. A lighter place. A different feeling.

One Wave Changed Everything

When we arrived at Sandy Island, we weren't expecting much. We saw families who clearly knew each other. Kids running between boats and adults laughing and talking with ease.

For a moment, it felt like the same story was about to repeat. Standing on the outside, watching something that wasn't ours.

And then someone turned around and waved.

Her name was Oda. She smiled at us, called her son, and told him to take our boys to meet the rest of the kids. It was such a tiny gesture that it almost shouldn't matter.

But it did.

Within minutes, the boys disappeared into a group of new friends. Within hours, we were sitting with adults who felt strangely familiar. Within days, we had a tribe. People who didn't need explanations for our life choices. People who understood the shape of our days and the rhythm of our decisions.

And suddenly, the loneliness that had been following us for almost a year softened. Not because we changed who we were, but because we were finally seen for who we already were.

What Remote Workers Need to Know About Loneliness

That moment taught me something that stayed with me in every part of my life, especially in remote work and long-distance living.

Loneliness doesn't come only from being alone. It comes from being slightly out of sync with the people around you.

And belonging doesn't come from effort or performance. It comes from finding the people you naturally settle into.

Remote workers know this feeling well. You can be in meetings all day and still feel like no one actually sees the work you do. You can carry the whole problem in your head and still have no one to think with. You can be responsible for clarity without having a single place where you get clarity back.

It's the same loneliness as choosing a different life. Brave on the outside, isolated on the inside, until you find the people who make you feel understood again.

Small Gestures Build Everything

Finding your people is not magic, and it's not luck. It's small moments, small risks, small openings, tiny gestures that turn strangers into something more.

Not every group will be your group. Not every place will feel like home. But it only takes one connection, one wave, one conversation, one shared moment to shift everything.

And once you find your people, something else happens - you start offering that same wave to others. You become the person who notices someone standing a little outside. You become the beginning of someone else's story.

Community is not built by perfect matches, it's built by people who are willing to meet each other halfway.

And that is true at sea, on land, and in every remote workspace.

Loneliness has momentum when we ignore it. Belonging has momentum when we reach out, even a little.

You are not alone. You can find your people, and when you do, you can be that wave for someone else.