How to Plan a Solo Trip You'll Actually Enjoy

How to Plan a Solo Trip You'll Actually Enjoy

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 go This 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 else * You're worried you'll do everything right, see all the right sights, and still come home feeling like you didn't really enjoy it * You keep a famous landmark on the itinerary just because you'd feel silly skipping it, even though you don't actually want to go * You'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 preferences * You already travel solo, or you want to, and you're ready for the how About 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 show [https://www.buzzsprout.com/2559400/support] Join 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/training [https://freedomlookslikethis.com/training] Email: contact@freedomlookslikethis.com Join Skool: https://freedomlookslikethis.com/community [https://freedomlookslikethis.com/community]

Your Adult Gap Year Doesn't Have to be a Year

We keep telling ourselves we'll take the trip we actually want once we've finally figured everything out. What if you have that backwards? You will not think your way to your next chapter from inside the old one, and the clarity you keep waiting for tends to arrive out in the doing, on the trip itself. This is the adult gap year, reimagined, and it does not have to be a year, or a leap, or anything as big as you are picturing. After all, this is not Eat, Pray, Love. In this episode: * The season you didn't choose * The trap of thinking harder * The habit discontinuity effect * A quiet month in Florence * Interrupting one autopilot This episode is for you if: * you're in a season that ended before you were ready, a role, a relationship, the shape of your household, and you keep waiting for clarity before you do anything about it * you've wanted a solo trip but told yourself you can't take the time, the job needs you, or you have to figure your whole life out first * you've been calling this stretch a transition, or limbo, and some part of you is ready to do something with it instead of waiting it out * you're a woman over 40 in a midlife transition who wants to feel like yourself again, not just keep showing up for everyone else * you already travel solo, or you want to, and you're ready for the how, and you've heard enough of the why About 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 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 show [https://www.buzzsprout.com/2559400/support] Join 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/training [https://freedomlookslikethis.com/training] Email: contact@freedomlookslikethis.com Join Skool: https://freedomlookslikethis.com/community [https://freedomlookslikethis.com/community]

This is the 40+ Solo Travel Advantage

Solo travel as a 40-year-old looks different from solo travel at 25 in ways that have very little to do with the budget or the boutique hotel. By 40 you already know what you want clearly enough to design a trip around it, and the work at this stage is to stop overriding yourself when something cheaper or more convenient shows up. This week Damianne tells the story of walking out of a Sapa travel agency with the wrong tour booked until she caught herself hours later. The 40+ solo travel advantage is clarity, and the work is to stop negotiating against yourself when you book. In this episode: * [00:00] The 40+ solo travel question * [07:03] Booking and unbooking the wrong tour * [14:21] What a private tour really gives * [17:28] The question that changed * [23:56] This week's invitation This episode is for you if: * you've talked yourself into the cheaper trip and then realised hours later it wasn't the one you wanted * you're a woman over 40 who knows what you want but keeps overriding it for someone else's idea of a good deal * you travel solo or want to, and you're still using rules you set at 25 about money, group tours, or eating on the go * you keep optimising your solo trips for cost or group availability when what you actually want is fit About 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 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 show [https://www.buzzsprout.com/2559400/support] Join 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/training [https://freedomlookslikethis.com/training] Email: contact@freedomlookslikethis.com Join Skool: https://freedomlookslikethis.com/community [https://freedomlookslikethis.com/community]

The Decisions That Build a Solo Traveler Aren't the Big Ones

The small decision on a Sunday morning, the park or the cafe or the hotel room, is building something that will help you for your solo trip. I took myself on an overnight trip to Olomouc in the Czech Republic, a city about three hours from Prague, because I was tired and I knew from experience that if I stayed home with a free weekend I would work. What the trip made visible was this: between where you are now and the solo trip you haven't booked yet, there are lots of small decisions that have been waiting for you to make them. I made a small decision to I leave the Museum of Modern Art in Olomouc after thirty minutes because I was done. There was judgment in that, the kind that asks whether you're cultured enough to stay longer. I noticed it, and I left anyway.. Psychologists call the relevant skill interoception: the ability to sense your own internal signals before you've reasoned your way to an answer. It's a skill, not a fixed trait, and it gets stronger the more you use it in low-stakes situations. Those situations, ordinary and small, are what build a solo traveler. That's the practice. Not the trip. In this episode: - Olomouc in late spring - Thirty minutes in the museum - Holy Trinity Column, covered - Park, cafe, or hotel room - Cognitive distance and the solo outing - The evidence account This episode is for you if: * ou've named the trip, know roughly where and when, but you still haven't booked anything * you're a woman over 40 who finds herself defaulting to the logical choice, and then wondering afterward why it didn't feel right * you've felt the slight pull toward something and then reasoned your way out of it before you had a chance to follow through * you're a solo female traveler who wants to understand what's actually building your capacity for bigger decisions, not just your ability to plan a trip Resources mentioned: * Go Alone guide: My free guide to taking yourself out alone, designed for step one of the process she describes in this episode. It walks you through how to design your solo outing, what to notice, and how to follow what surfaces. Free at freedomlookslikethis.com/goalone [https://freedomlookslikethis.com/goalone] * Free workshop, May 30th: a live online session with Damianne for women ready to take the next step toward solo travel. Details at freedomlookslikethis.com/training [https://freedomlookslikethis.com/training] About 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 start moving. New episodes every Wednesday. Support the show [https://www.buzzsprout.com/2559400/support] Join 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/training [https://freedomlookslikethis.com/training] Email: contact@freedomlookslikethis.com Join Skool: https://freedomlookslikethis.com/community [https://freedomlookslikethis.com/community]

Searching vs. Meeting Yourself as a Solo Traveler

I'm sharing a conversation from Kellie Stirling's podcast Talkin About Midlife [https://podcasts.apple.com/us/podcast/talkin-about-midlife/id1490365703] where I'm visiting as a guest rather than a solo host or interviewer. We started from the very beginning: Saint Lucia at birth, Canada at 12, then India for my first teaching job, then Sudan, Japan, and finally Prague, where I've been for thirteen years.  Somewhere in all of that, a Sufi teacher in India said something to me in my mid-twenties that's still relevant to me and an important reminder more than twenty years later. It directly connects to one of my key ideas these days: there is a real difference between searching for yourself and meeting yourself. In this episode: * Saint Lucia to Prague * The Sufi teacher's reading * Training the nervous system abroad * Searching vs. meeting yourself * Midlife, identity, and new roles * 20% more enjoyment This episode is for you if: * You've been traveling for years and still feel like you're looking for something, and you're not sure whether you're going toward it or away from it * You're a woman over 40 who wants to hear the full long version of how someone became a solo traveler, not the edited highlight version where it all clicked one afternoon * You want to understand what actually separates intentional solo travel from just going somewhere alone, because you've been wondering if you're doing it right * You've heard of the RAIN meditation but never heard someone describe using it while buried in fermented rice sand in Japan, with cotton balls in their ears Free Resources: * Damianne's free guide to start solo travel [https://freedomlookslikethis.com/solo-travel-starter-gift/] * Decide Your Trip [https://freedomlookslikethis.com/training/] workshop to figure out your first or next solo trip Meet Kellie Stirling: Kellie is the host of Talkin About Midlife, a podcast about life, health, love, relationships, the inner world, aging, and what it means to be human in a female body at this time in life. Kellie is also a somatic experiencing practitioner. Find her show wherever you listen to podcasts. Learn more about her podcast and follow at https://www.kelliestirling.com/podcasts [https://www.kelliestirling.com/podcasts] About 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 start moving. New episodes every Tuesday. For solo female travelers, midlife women, and anyone who suspects that the real barrier isn't logistics. Email: contact@changesbigandsmall.com Support the show [https://www.buzzsprout.com/2559400/support] Join 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/training [https://freedomlookslikethis.com/training] Email: contact@freedomlookslikethis.com Join Skool: https://freedomlookslikethis.com/community [https://freedomlookslikethis.com/community]