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

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

Email: contact@freedomlookslikethis.com

Join Skool: https://freedomlookslikethis.com/community

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

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

Email: contact@freedomlookslikethis.com

Join Skool: https://freedomlookslikethis.com/community

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

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

Email: contact@freedomlookslikethis.com

Join Skool: https://freedomlookslikethis.com/community

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
• 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

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

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

Email: contact@freedomlookslikethis.com

Join Skool: https://freedomlookslikethis.com/community

I'm sharing a conversation from Kellie Stirling's podcast Talkin About Midlife 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
• Decide Your Trip 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


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

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

Email: contact@freedomlookslikethis.com

Join Skool: https://freedomlookslikethis.com/community

Most women have a definition of solo travel in their head, and it's usually the thing keeping them from taking the trip they dream of. If solo means handling every unknown by yourself with no one to call on, of course you're not booking the trip.

Gina Cambridge built her business as a travel coach on the gap between that definition and what solo travel can actually look like.

In this episode of Freedom Looks Like this, we talk about solo travel retreats within a group tour and how that still counts. Gina has led over 30 retreats and tours across destinations like New Zealand, Bali, and Cuba. We also get into safety abroad and the difference between what the news tells you about a place and what living there actually feels like.

In this episode:

• Group tours that still count as solo
• Snoring, single rooms, and matchmaking
• The bunk bed that led to Bali
• Lunch with the phone put away
• Cairo, giggling, and going alone
• The family beach day and permission

This episode is for you if:

• you are curious about taking a group trip
• you've considered a group tour but worried about choosing the right one
• you're an introvert who wonders how anyone is supposed to make friends on the road, especially with everyone glued to their phones
• you've taken solo trips before and want to try different approaches

Resources mentioned:

• Gina Cambridge's free guide to Fearless Solo Travel
• Wanderlust Solo Women Tours
• Gina's podcast Wanderlust Solo Women Travel "Unscripted" on YouTube
• Gina on Instagram: @wanderlust_momentum and @wanderlust_travel_coach
• Gina on LinkedIn
• Gina on Facebook

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. For solo female travelers, midlife women, and anyone who suspects that the real barrier isn't logistics.

Support the show

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

Email: contact@freedomlookslikethis.com

Join Skool: https://freedomlookslikethis.com/community

Maybe you've been thinking about a trip for months, looking at flights, reading about the destination, knowing roughly what's there. And still not booking. Or you've already been on the trip and running a calculation the whole time: how do I make this count? Was this worth it? Both versions have the same problem. The question you're asking doesn't close. It just generates more conditions.

In this episode, Damianne introduces the two-word question she's used for years, one that doesn't require a perfect reason to go, just the absence of a real blocker. With three stories from three very different decisions, she traces how the same question opened doors she couldn't have planned for, including thirteen years in a city she'd never seen before she arrived.

The "why should I go" question has a problem: it's designed for explanation, for optimization. It needs a good reason, and so it's easy to delay. Instead, you generate concerns. Address one, and another appears. The timing isn't right. The savings aren't there. Something at work needs you.

Solo travel for women over 40 isn't really a logistics problem. It's a question. So we need to ask better questions.

In this episode:

• The cherry blossom calculation
• The question that keeps generating conditions
• Two words and how they work
• Off the main path in Sapa
• A pyramid in Tirana
• Thirteen years late

This episode is for you if:

• you've been looking at flights for a trip you haven't booked, and you're genuinely not sure what you're waiting for
• you travel solo and find yourself measuring the experience instead of just being in it
• you're a woman over 40 who wants to stop generating conditions and start deciding
• you've answered one concern about a trip only to find another one waiting in its place

Resources mentioned:

Free workshop — freedomlookslikethis.com/training

Make the trip decision in a small group with Damianne. Next session: June 6.

Support the show

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

Email: contact@freedomlookslikethis.com

Join Skool: https://freedomlookslikethis.com/community

You probably have a condition before you'll book the trip, something that needs to be true first. But if you look back, a version of that condition has likely already been true. You met it, and then something else came up. The timing wasn't right, and then it was, and something else came up. There was always something.

This is what practising deferral looks like. Every time you defer, you're getting better at putting yourself last. And after a while, that feels natural. It looks responsible, from the inside and the outside. But the woman you're becoming while you practise it is the one who doesn't quite trust herself to choose. That accumulates. And it compounds.

The clarity and confidence you're waiting for don't come before the decision. They come after you've moved.

In this episode:

- Conditions that keep moving to stay out of reach
- Building evidence, for or against yourself
- The school bus in September
- Nine months without a plan, but moving
- Writing the trip as a decision

This episode is for you if:

• you've been wanting to take a solo trip and keep finding reasons to wait
• you're a woman over 40 who makes thoughtful, reliable decisions for other people all day and can't quite remember the last time you made one that was purely for yourself
• you're a solo female traveler or seriously thinking about becoming one
• you've been telling yourself you're being responsible by waiting, and some part of you suspects that framing is doing double duty as a reason to stay put.
  
  Resources mentioned:
• The Science of Well-Being: a free online course on happiness, with Laurie Santos
• Learning How to Learn: an online course on approaching new skills and subjects, with Barbara Oakley
  
  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. For solo female travelers, midlife women, and anyone who suspects that the real barrier isn't logistics.

Support the show

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

Email: contact@freedomlookslikethis.com

Join Skool: https://freedomlookslikethis.com/community