do you really need to plan it all in advance?


Hi Reader,

As I was leaving a coffee shop in Shirahama, Japan, a staff member stepped outside at the same time and said something to me in Japanese. My default (the one I've had for years) is to smile, nod, and keep moving. It's easier and less awkward.

But this time I stopped. I asked what she said. And it turned out she spoke English. We stood on the street and had a proper little conversation. She'd had an English teacher from the Czech Republic. What are the odds?

When I walked away, I had this feeling that in another life we would have been friends. It made me think about something I hear a lot when people are considering solo travel: you have to plan everything in advance or the trip won't work.

I get it. When I first started traveling solo seriously, I wanted every detail locked in. It felt like control. Like safety. But you can't plan for the moments that actually change you. You can only leave a little room for them.

So here's where I'd start: get the essentials sorted. Where you're sleeping, how you're getting there, one or two things you genuinely want to do. Then leave at least one day (or even half a day) deliberately open. Not empty because you ran out of time to plan. Open on purpose.

The conversations, the gift of extra meat from a chef who noticed, the unexpected facial where you end up chatting back and forth via Google Translate, an unexpected conversation with a chef when you end up having omakase with no one else in the restaurant ... none of that fits on an itinerary because you can't plan for them. And those are the things I'm still thinking about weeks later.

You don't need a perfect plan. You need just enough of one and a little (or a lot of) curiosity.

You can do this.

Joyfully, Damianne

PS: This is what episode 23 is really about. 🎧 Traveling Alone Doesn't Change You. Your Decisions Do.​

You made it all the way to the end? Here's a picture of my omakase dinner. This was the best squid I ever had in my life and another of the Chef grilling something before serving it.

chef lightly searing something at range the best squid of my life.

Podcaster & Coach

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Freedom Looks Like This

A newsletter for women over 40 who are tired of making "good" decisions instead of their own. From the host of Freedom Looks Like This. Solo travel as a way back to yourself.

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