Freedom Looks Like This – solo travel for women over 40 ready to choose themselves

Someone says a trip is too expensive, and someone else hears "I don't have the money," when what she actually meant was "I would never spend that much on a holiday." I used to say I couldn't afford things by default, and it took me years, and a $500 star sapphire in India, to realise that I didn't know what I meant when I said it. So what do you mean when you say you can't afford a trip?

In this episode:

• A star sapphire in India
• Several sentences, same words
• Mental accounting and the "too much" jar
• How I actually decide
• Saying no to $25,000
• Japan, but not right now

This episode is for you if:

• You've said "I can't afford it" about a trip without stopping to ask what you really meant
• You're a woman over 40 who is careful with money and still feels guilty spending it on yourself
• You dream about solo travel, but the trip keeps landing in the "maybe someday" pile
• You want to make money decisions that fit your own values, not someone else's rules

Resources mentioned:

• Mark Butler on Changes Big and Small, episode 74: the conversation that changed how I think about "expensive"
• Mental accounting, Richard Thaler's research on how we sort money into mental jars
• Episode 42 with Jillian Johnsrud, on pricing a trip line by line
• The Solo Trip Fit Finder

Support the show

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.

Email: [email protected]

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

Most of us say "I can't afford it" about a trip before we've ever sat down and worked out what it would cost. What if the number you keep saying no to is one you've never actually looked at?

Jillian Johnsrud, author of Retire Often, has taken more than a dozen mini retirements, and she explains why a month away rarely costs what we imagine. She gives us a surprisingly easy way to turn a someday trip into a real decision you can make.

In this episode:

• Mini retirements, not holidays
• Chipotle or salsa dancing in Mexico
• The $12,000 math mistake
• A $20,000 week in Paris
• Starting with a one- or two-week trip

This episode is for you if:

• You've said "I can't afford it" about a trip you've never actually priced
• You're a woman over 40 who wants to travel solo and money feels like the wall you keep hitting
• You only have a week or two of leave and wonder whether any of this applies to you
• You're curious how a mini retirement or sabbatical could fit around your work and your life

Resources mentioned:

• Retire Often by Jillian Johnsrud: her book on planning a month or more away from work, available wherever books are sold
• Jillian's website and newsletter: https://www.jillianjohnsrud.com
• Jillian on Instagram: https://www.instagram.com/jillianjohnsrud/

Support the show

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.

Email: [email protected]

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

Even when the place is beautiful and you are grateful to be there, a trip can still leave you depleted.

I used to think that meant I had chosen wrong. 

What I have come to think is that it is a question of fit, between what a place asks you to carry and what you were already carrying when you arrived. This one is from the vault, and it starts with a very long day in Kandy.

In this episode:

• The twelve-hour tour
• Two measurement systems
• Rain on the museum roof
• What you're already carrying

This episode is for you if:

• You came home from a good trip more tired than when you left, and you have never quite worked out why
• You're a solo female traveler who keeps adding one more stop because somebody said you should
• You're a woman over 40 fitting travel around work, and the weekends are not restoring you
• You have let somebody else decide what counts as worth seeing

Take my fit finder quiz here: https://freedomlookslikethis.com/solo-trip-personality-quiz/

Support the show

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.

Email: [email protected]

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

I was on a walkway in Brazil, soaked through, my raincoat sitting on the bus, walking back as fast as I could and repeating under my breath, "This is crazy." Most weeks I talk about solo travel as practice for self-trust. But that Saturday at Iguazu Falls wasn't about practicing anything. And it made me wonder why so many of us need a reason before we let ourselves have the thing we love.

In this episode:

• An update from the road
• The coati and the alfajor
• Two sisters from below
• A raincoat on the bus
• Three frontiers
• Love is a reason

This episode is for you if:

• you only let yourself go when you're burnt out enough to have earned it
• you're a woman over 40 who keeps putting the thing you love behind everybody else's needs
• you travel solo, or with friends, and are intrigued when you hear "pure delight"
• you've ever felt you had to justify a trip before it felt allowed
  
  

Resources mentioned:

• Iguazu Falls blog post with photos
• Live Lab founding cohort available for $147.47, closes September 28 at 12:00 UTC. Email [email protected].
  
  

Support the show

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.

Email: [email protected]

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

By the time I actually landed in Lagos, everyone else had already been there for a full day because my visa came through late. Once I was there, surrounded by family for my stepmother's 61st birthday, the same skills solo travel built in me were still firing, in taking Uber to the grocery store, in figuring out a food delivery app alone in my room. How could this trip be mine as much as it was ours? I think the answer is yes.

In this episode:

• The delayed landing in Lagos
• Traveling with family
• The Uber grocery run
• Self-efficacy, defined
• Mine as much as ours

This episode is for you if:

• You've wondered if solo travel confidence holds up once you're surrounded by family again
• You're planning a family or group trip and are worried you'll lose the version of yourself solo travel built
• You're a woman over 40 who notices old family patterns showing up the moment you're back in familiar situations
• You've ever reached for the easier, hands-off version of something instead of figuring it out yourself and wondered what that choice actually costs you

Resources mentioned:

Episode 36 with Kristine Madera about belonging as a set of skills you build

Support the show

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.

Email: [email protected]

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

I was standing in the corner of Edinburgh airport with two suitcases, a backpack, a side bag, and no visa, making call after call that went nowhere. The plan had been for my whole family to fly to Lagos together for my stepmother's 61st birthday. I had to let go of that plan at eight in the morning and what actually got me through the experience wasn't the thing I expected.

In this episode:

• Checking the visa portal all night
•  Alone at the Edinburgh check-in
• The woman without the visa
• Trying to switch to Ghana instead
• Buying two new tickets
• Six hours in the airport lounge
• Landing in Lagos

This episode is for you if:

• You've had travel plans nearly fall apart the night before you were supposed to leave
• You're a woman over 40 traveling with family and still figuring out how much of the decision-making is yours
• You've assumed a plan would hold and didn't check it until it was almost too late
• You're a solo female traveler who wants to hear what actually gets you through a travel disaster, not the highlight reel

Support the show

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.

Email: [email protected]

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

I'm bringing this one back from the vault. I recorded it in April, before this month took me through Nigeria, Ghana, and Rwanda, and before I missed an episode for the first time because I didn't have reliable internet. It still holds up. The next two episodes are going to get specific about this trip, the Nigerian visa that almost didn't come through in time, and what I learned about connecting with strangers.

I left a fourteen-year teaching career without knowing what would come next. I remember standing on a balcony in Canada that September, watching a school bus go by, and feeling relief instead of grief. That relief was the confirmation, not a plan. Since then I've spent three months living as a digital nomad in Southeast Asia and built a life I would not have believed was available to me back then. None of it started with feeling ready. It started with one decision I was willing to name.

In this episode:

- The planning meeting that broke something
- Watching the school bus go by
- The conditions that kept multiplying
- Clarity comes in the decision
- Three months as a digital nomad
- Naming the trip as a decision

This episode is for you if:

• you keep waiting for one more condition to be met before you'll book the trip
• you're a woman over 40 who left something certain for something you couldn't yet imagine
• you think clarity has to arrive before the decision instead of inside it
• you've been telling people about a trip for longer than six months and still haven't named a date
• you've caught yourself treating "someday" as a real plan instead of a way of avoiding one

Resources mentioned:

• Laurie Santos's course The Science of Wellbeint
• Barbara Oakley's Learning How to Learn
  
  

Support the show

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.

Email: [email protected]

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

You never find somebody who's just like you, not even twins. My guest today, Kristine Madera, has backpacked solo through China, Russia, and the Baltics during the fall of the Soviet Union, served in the Peace Corps in Papua New Guinea, taught English in Japan, and spent years since teaching other travelers how to belong in cultures that were never built around them.

We get into the two-minute trick a Peace Corps trainer taught women stationed in Papua New Guinea, why small talk is never actually small when you're the one traveling alone, what to do when someone comes on too strong in a culture that isn't yours, and what it means to belong

In this episode: 

• The Dali hostel, sixteen strangers, one hour
• Belonging to yourself
• The Papua New Guinea micro-tribe trick
• Small talk as the door
• Pacing yourself as an introverts
• Practicing curiosity as a skill

This episode is for you if: 

• you've walked into a room full of strangers and felt like everyone else already knew each other
• you're a solo female traveler who wants real connection, not just polite distance
• you're an introvert, or a recovering shy introvert, who assumes small talk isn't for you
• you're a woman over 40 who's curious about other cultures but isn't sure where you actually belong in them
• you've ever needed permission to say "I just need a few minutes"

For more from Kristine, see The Art of Belonging (free guide)

Support the show

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.

Email: [email protected]

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

I recorded this one a while back, and in it I explore a feeling so many of us have after 40, where you walk into a room and somehow nobody quite registers that you're there. Back then I thought the answer was to be seen again, to be noticed, and that if I could just be visible then the rest would sort itself out. I'd say it a bit differently now.

I've pulled the episode from the vault because the question underneath it still holds up. I talk about the small everyday versions of this and why travel makes all  so hard to ignore.

Here's what I've come to think since. Invisibility isn't really the deepest problem.  While I've left the original episode the way it was,  at the end I come back and add the part I didn't have words for yet, plus a small invitation you can actually try this week.

In this episode:

• Airports and overhead bins
• The chocolate shop in Oman
• When waiting becomes a habit
• Fight, flight, freeze, fawn
• The cost of walking away
• Chosen vs. imposed invisibility
• Becoming visible to yourself first
• What I'd add now

This episode is for you if:

• you've stood clearly next in line and watched someone who arrived after you get helped first
• you travel solo, or you're thinking about it, and you've felt strangely easy to overlook when there's no one beside you
• you're a woman over 40 who's tired of having to remind the world that you're right here
• you've felt that heat rise up in you when you're passed over, and you don't want to have to beg to be seen
• you've wondered whether letting it go keeps the peace, or slowly trains you to abandon yourself

Resources mentioned:

Take the solo travel quiz at https://freedomlookslikethis.com/solo-trip-fit/

Support the show

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.

Email: [email protected]

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

A lot of us have a list somewhere, in a notes app or just in the back of our heads, of places we'd like to visit. Every place on it sounds lovely, and not one of them is an obvious yes. So we keep researching, and we keep not choosing.

What if the way you've been choosing where to go is the very thing keeping you home? The best destination for you probably isn't the one the lists keep pushing, and it isn't the safest or the most impressive one either. There's a different question to ask first, and most of us have never been taught to ask it.

This episode gets into why researching more makes the choice harder instead of easier, the reason a place that looks perfect online can leave you feeling almost nothing once you're standing in it, and four feelings I've chosen trips around, along with the very different places that gave them to me. The places are mine. The question underneath them might change how you pick your next one.

In this episode:

• The 15 best places trap
• Situation selection, explained
• Four feelings
• Your invitation

This episode is for you if:

• you've saved a dozen versions of "the 10 best places for solo women over 40" and still can't commit to one
• you travel solo, or want to, and every option feels reasonable but none of them feels like yours
• you're a woman over 40 who has gotten so good at the sensible choice that the muscle for choosing what you actually want has gone quiet
• you once did the bucket-list trip and felt almost nothing, and you've never quite known why

Resources mentioned:

Take the solo trip personality quiz at freedomlookslikethis.com/solo-trip-fit/.

Support the show

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.

Email: [email protected]

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