How to Plan a Solo Trip You'll Actually Enjoy episode artwork

EPISODE · Jun 10, 2026 · 25 MIN

How to Plan a Solo Trip You'll Actually Enjoy

from Freedom Looks Like This – solo travel back to yourself · host Damianne President – solo travel for women over 40

We plan our trips around the famous sights, the must-do list, the things we'd feel a little silly skipping. And then we come home exhausted, having seen everything without focusing on enjoyment.What if the trip you'll actually enjoy is the one you subtract down to yourself? Think about the best afternoon you've ever had on a trip. I'd bet it wasn't the landmark everyone photographs. It might even be something you'd never have written on an itinerary, and you still think about it months later with a smile.This episode is about how to plan a solo trip around the woman who is actually going, not the one you think you should be, and it doesn't start with where to go but with a better question that prioritizes your enjoyment.We focus on a trip built for delight instead of for more, more, more, and the simple reason a choice that genuinely fits you, what psychologists call self-concordant, is the one you put more into and get more back out of.In this episode:- The afternoon that wasn't on the list- The myth of the one right trip- The subtraction effect- Being good company for yourself- The Krakow evening I skipped the sights- One swap before you goThis episode is for you if:You've decided you want to travel solo and the planning advice you keep finding feels like it's written for somebody elseYou're worried you'll do everything right, see all the right sights, and still come home feeling like you didn't really enjoy itYou keep a famous landmark on the itinerary just because you'd feel silly skipping it, even though you don't actually want to goYou're a woman over 40 who wants a trip that fits the woman you are now, not a twenty-two-year-old backpacker with no preferencesYou already travel solo, or you want to, and you're ready for the howAbout Freedom Looks Like This:Freedom Looks Like This is a podcast for women over 40 who want to travel solo, or who already do, and want to go deeper. Host Damianne President explores self-trust, decision-making, and what it actually takes to stop waiting and give yourself permission to start moving. New episodes every Tuesday. For solo female travelers, midlife women, and anyone who suspects that the real barrier isn't logistics.Support the showJoin the next Solo Trip Decision Workshop live on June 20. It's for women who've decided they want to take a solo trip and want help deciding the trip they actually want: https://freedomlookslikethis.com/trainingEmail: [email protected] Skool: https://freedomlookslikethis.com/community

Episode metadata supplied by the publisher feed · Published Jun 10, 2026

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We plan our trips around the famous sights, the must-do list, the things we'd feel a little silly skipping. And then we come home exhausted, having seen everything without focusing on enjoyment. What if the trip you'll actually enjoy is the one you subtract down to yourself? Think about the best afternoon you've ever had on a trip. I'd bet it wasn't the landmark everyone photographs. It might even be something you'd never have written on an itinerary, and you still think about it months later...

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How to Plan a Solo Trip You'll Actually Enjoy

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This episode was published on June 10, 2026.

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