I’ve been thinking a lot about what we expect from a first solo trip, especially later in life. There’s often an unspoken belief that if we plan carefully enough, choose the right destination, book the right hotel, and think everything through, the trip should go smoothly. It should feel relaxing. A “perfect” trip confirms that we made the right decision to go on our own.

When I look at my own life, that expectation doesn’t match reality. Even the days I think of as good days usually involve small adjustments. Something changes or doesn’t work quite the way I thought it would. I adapt and move on. Days that require no adjustment at all are actually pretty rare.

So it’s worth asking why we expect a solo trip in a new place, with unfamiliar systems and customs, to be any different.

When things go wrong on a solo trip

When something goes wrong on a trip, even something small, our reaction can feel surprisingly strong. I notice how quickly my mind moves into self-blame. I start replaying what I should have done differently, how I should have been more careful, more organized, more prepared. That same pattern exists in my life at home, but it gets louder when I’m away.

I don’t know the systems as well when I travel somewhere new. Time feels more limited and there’s this pressure that the trip is supposed to be a break. I catch myself thinking things like, “This shouldn’t be happening,” or “Why is this happening now?” So I’m not only dealing with the problem itself. I’m also dealing with the frustration of feeling like I’m doing my holiday wrong.

Small mistakes and familiar shame

I’ve locked myself out of my hotel room more than once. I’ve shown up convinced I had a reservation, only to be told I didn’t. I’ve had deliveries sent to the wrong address even when I typed everything in carefully. None of these things are dramatic. But they bring up a surprising amount of embarrassment for me.

Part of that comes from how strongly I identify with being capable. I’m the oldest child in my family, and from a young age, being capable felt like how I stayed safe in the world. It wasn’t something anyone formally taught me. It just became clear that I could handle things and figure things out. That identity followed me into adulthood and into solo travel. When something goes wrong, it can feel like a personal failure instead of a normal human mistake.

Learning to meet myself differently

I still have to work at meeting myself with any kindness in those moments. Sometimes that looks like stopping and saying to myself, “It’s okay, sweetheart.” That doesn’t come naturally. It’s a practice.

Over time, solo travel has shown me that control doesn’t prevent things from going wrong. It mostly just exhausts me when they do. What actually helps is staying present with what’s happening and asking a simpler question: what’s mine to respond to right now, and what isn’t?

Some of the most memorable experiences I’ve had both while traveling alone and at home came from things not going according to plan, like getting lost in a city I thought I knew and ending up somewhere unexpected. It also gives a chance to be helped by strangers in ways I couldn’t have anticipated.

Why “wrong” isn’t a problem

I don’t think a first solo trip needs to go smoothly. I think it needs to go honestly. The moments that feel awkward or uncomfortable are often the ones that show you what you can handle. That’s where self-trust gets built. We expect it to happen through perfect planning, but it happens through lived experience.

If you’re considering traveling alone and worried about getting things wrong, it helps to let go of the idea that mistakes mean failure. Most of the time, they just mean you’re in the middle of learning something.

An invitation

If this brings anything up for you, you don’t need to resolve it all at once. Just notice the next time something small goes wrong on a trip, or even at home how quickly you turn on yourself. You might notice the urge to fix, to control or to explain why you should have known better by now. If you catch that moment, even briefly, see what happens if you pause. Remind yourself that you’re human, and that nothing needs to be proven right then.

Join the community

And if you want a place to explore these questions more slowly, with other women who are thinking about solo travel in this season of life, you’re welcome in the Skool community. It’s a space to talk honestly about what comes up, without pressure to be brave or get it right.