From High Heels to Hiking Boots: How I Reinvented My Life to Travel Full Time

by | Nov 19, 2023

hiking boots travel full time adventure
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Last updated on November 30th, 2023

Featured image: The life of your dreams starts with a single step forward/ Photo by  Meniphoto via Envator  

Reinvention isn’t about age, it’s about embracing the joy of uncertainty

by Carolyn Ray

November 2023 is a milestone month for me. It marks my fifth anniversary of the beginning of what some might call my ‘midlife reinvention’.  As it happened, I turned 50 in 2018, but I don’t think my decision to rethink my life was age-related. We can – and do – reinvent ourselves all the time. Sometimes it’s small, and other times it can be life-changing, as it was for me when I decided to travel full time.

How to travel full time: Six shifts

In these five years, I’ve gone from high heels to hiking boots. I’ve travelled to places I had only read about, and many I knew nothing about. I’ve shifted from spending money on things to investing in experiences. From owning a three-bedroom house to living anywhere in the world. I’ve learned that it only takes a first step to make dreams happen. Instead of fearing the future, I embrace the unexpected. In these past five years, I’ve come to see that joy is the only antidote to fear — and that I have alone the power to create the life I want for myself, not wistfully expect it to suddenly appear.

1. From high heels to hiking boots

Let’s be clear about something. When I decided to pursue a life of travel full time, I wasn’t unhappy. I didn’t feel unfulfilled. I didn’t lack purpose. I didn’t have people who were unsupportive around me. I loved my career in consulting. I just wanted to do something different. After 30 years of managing a fast-paced, busy career, and raising a daughter as a single mom, I wanted to slow down. I wanted a simpler life. But most of all, I was curious to learn more about the world.

It didn’t happen all at once. In 2017, I left my successful six-figure corporate job as the CEO of a global consultancy to start my own business. A year later, when I turned 50, I travelled to Kenya’s Maasai Mara on a service trip with Alyxandra, my then 18-year-old daughter, who was starting university in the fall. Meeting so many people who were living joyfully, in harmony with nature, was an awakening for me. Looking at my own life, I felt as if I had fallen into the trap of consumerism and lost my connection with the world.

I returned home to a house I loved, looked around its overflowing rooms, and decided it was time to change. Why was I spending weekends acquiring things and watching travel shows on TV instead of doing what I really wanted to do — learn about the world through travel. I also decided that everything had to go. For years I had played by the rules. I didn’t want to be constrained by material possessions anymore.

Blue-footed Boobie Galapagos Ecuador
Alyxandra and Carolyn at a school in Kenya, August 2018/ Photo credit Carolyn Ray
horse banff alberta midlife reinvention
Horseback riding in Banff, Alberta’s backcountry in August 2020/ Photo credit Carolyn Ray

2. From a house to a backpack

Within six weeks, I put my house on the market, sold it and liquidated everything in it. I hired a company to auction off the contents, donated my clothing to non-profits, and gave the rest to friends. This was no small feat. I had lived in this house for almost 15 years, raised my daughter in it, and accumulated far more possessions than I had realized. I was embarrassed when I started going through the boxes of clothing, high school memorabilia and baby toys. My basement had turned into a storage locker for my family. Why did I have all these things?

My biggest hurdle was separating my identity and sense of self from these things. I had been fortunate to inherit most of my furniture from my grandparents. It was old and banged up but it felt like a part of me. Every piece of furniture had a childhood memory attached to it. I had to tell myself that I had done my part, that it was okay to let someone else love it as I had. Silly as it sounds, meeting the people who bought my family heirlooms at the auction helped. It was cathartic — I was able to tell them the history of a favourite chair or lamp, and the stories that were intrinsically tied up in these items.

When I walked out the front door of my house for the last time sense, I felt an overwhelming sense of relief and gratitude. Somehow I had liberated myself. For the first time in my life, I didn’t have a mortgage, household expenses or anything to worry about. I could start on my new journey. I was free.

Carolyn stands with her Gregory backpack

At the airport in November 2021, leaving for my first three-month long stay in Mexico / Photo by Carolyn Ray

travel full tme

My definition of freedom is owning as little as possible/ Photo by Carolyn Ray

3. From watching life happen to living life

I moved into a furnished apartment in downtown Toronto, intending to stay for a few months while I planned out my worldwide journey. I started researching UNESCO World Heritage sites, and created my own travel wall, with a map of the world covered in hundreds of sticky notes.

My only guide was intuition and impulse. Ethiopia’s Rock-Hewn Churches, Croatia’s old city of Dubrovnik, Ecuador’s Galapagos Islands, the ancient city of Petra in Jordan. I wondered if it was possible to take a freighter around the world. Even though I had travelled extensively, the idea of going around the world for months for long periods of time was intimidating. But there had to be a way, right?

4. From dreaming about what could be to making it happen

Aside from my daughter, there are three things I’m passionate about: writing, women’s stories and travel. For years, I had dreamed about being a travel writer, but I had no idea what that meant. I decided to do a pilot trip to Puerto Rico, where I stayed for a month. I started writing and created an Instagram account called ‘wisdom and wonder’ to share my travels. Then, something unexpected happened.

Early in 2019, I was having lunch with my friend Erica. She was distraught. Not only was her mother very sick with cancer, but Erica was also concerned about her mom’s business, a beloved website for solo women. At the time, I was planning a trip to Spain, and carrying on about my travel plans. I’ll never forget the moment when she looked at me with a strange look on her face and said: “You. You should carry on my mother’s business.”

That business was JourneyWoman, the world’s first website for solo women travellers. After many discussions and a huge leap of faith, I agreed to buy it. A few weeks later, I went to visit Evelyn in the hospital. Erica and her sister Leslie and I sat with Evelyn, and told her JourneyWoman was in good hands. Two days later, Evelyn passed away. Over the next six months, with Erica by my side, we announced my purchase of JourneyWoman and redesigned it, relaunching the website in March 2020.

These photos, taken years apart, were a sign from the universe to do it/ Photo by Carolyn Ray
5. From fear of uncertainty to trusting the universe

When I agreed to take over JourneyWoman, I thought I had purchased a website. I soon found out that JourneyWoman is so much more than that. It’s very special and unique, because of how Evelyn created it. It’s not just a website — it’s also a community of women, who, arm in arm with Evelyn, discovered themselves through travel. She was the vanguard of that community, always out in front, willing to go courageously where others didn’t. She inspired thousands of women to follow their hearts and make their dreams happen. To take that first step.

Over the past four years, I’ve tried to do the same. In doing so, I’ve discovered strengths within myself that I didn’t know existed. While I don’t have a fear of travelling solo, I still have a fear of uncertainty, especially after the pandemic. I like to do research, plan and put detailed itineraries together. I like to have enough knowledge to make me confident, so that I can deal with the unexpected.

Journey Woman acquired by Carolyn Ray
Erica Ehm and Carolyn Ray: Transitioning a legacy, with Evelyn’s red boots and an original JourneyWoman newsletter from 1995 / Photo by Carolyn Ray

Never was I prepared for almost three years of a global pandemic, which basically stopped me in my tracks. But I adapted. For the two years when travel was curtailed, JourneyWoman became a place of learning and community, with weekly community calls, webinars, book clubs and articles that explored the wisdom of women. I travelled at home, hosted meetups and found different ways to explore the world.

6. From following the rules to following my heart

When the world started to open up again, I decided to say yes to everything, even if it scared me. I was still determined to make my dream of full time travel real. I learned to ride horses in the backcountry in Banff in August 2021. In September, I walked 120 kilometres of Spain’s Camino de Santiago, never imagining I could actually walk 12 kilometres a day.

In the past four years, I have travelled to places I had only watched movies about.  In 2022, I went to 17 countries, including Colombia, Panama, Mexico and several European countries. My travels surprised even me, and I ended the year in Malaga, Spain, where I lived for two months.

This year, I went to the Galapagos, the Ecuadorean Andes and the Amazon. I went on my first expedition cruise through the Suez Canal and Red Sea to Egypt, Jordan, Saudi Arabia, Djibouti, Dubai and Socotra (Yemen).  I now spend my winters exploring one country during the off-season, where I can truly immerse myself in a place and see it at a less expensive time when there are no crowds and very few tourists.

Carolyn in Ecuador Cotapaxi
Over 16,000 feet up, with Cotapaxi Volcano in the background, Ecuadorian Andes, August 2023 / Photo credit Carolyn Ray
egypt giza
In Giza, Egypt exploring the pyramids in October 2023 / Photo credit Carolyn Ray

Travel full time: A journey in progress

During the pandemic, I bought a small 500-square-foot apartment in Toronto instead of paying rent. It’s all I need. My only expenses are my mortgage, a utility bill, an annual insurance policy for travel, phone service and public transit. I don’t have television or cable anymore, just Internet, which I pause when I travel. I recycle, repair and thrift my clothes. When I travel, I try to go in the off-season, negotiate longer stays, fly on points, use buses and trains and try to eat in. That said, food is significantly cheaper (and fresher) outside North America, so I feel like I’m saving money and eat healthier when I live in other countries.

Being a travel writer might look glamorous but it’s hard work. I can tell you that none of us are doing it to make money. We don’t ‘travel for free’, especially me, since it’s a lifestyle decision, not just a career. I do this because I love it, and because nothing gives me more joy than seeing women start their journey of self-discovery and inspire others to take their first step. I am often brought to tears by emails I receive, from a woman who has been touched by our articles, or has found a life-changing trip in our Women’s Travel Directory. Or by women in our private Facebook group who are vulnerable and receive such positive encouragement from others to JFDI! That makes it all worthwhile. I can’t imagine a better and more fulfilling purpose.

As JourneyWoman celebrates our 30th anniversary in 2024, and I continue the second half of my life, I think a lot about my legacy. But my most important audience is my daughter, who’s now 23 and graduating with her master’s degree in London, UK. What will she say about me? Is she proud of me? Am I a good role model for her? Is she learning from me?

She’s currently on a trip with her friend in Vietnam, one she planned and organized, trekking in the mountains, staying in hostels and eating street food. So far, I think I’m doing all right.  And yes, my hiking boots go with me everywhere now — they are a symbol of my own freedom and a reminder that we can all live the life of our dreams. It just takes that first step. You can do it!

What I’ve learned about how to travel full time

I’ve learned so much in these past four years as I’ve pursued my dream of full-time travel. When we talk about living the life of our dreams, what we’re really talking about is saying yes to the unknown. And then finding the courage to do it. Life isn’t about what you know, it’s about what you don’t know. Isn’t that a magical idea?

 1. Know that the world is waiting for you – say yes!

Every day we are invited to do something new. It might be something that scares us or makes us uncomfortable. That’s often good! We have a choice. We can say no and stay comfortable where we are or we can say yes and discover something new. Be open to all your potential and say yes.

2. Channel your fear and use it to your benefit

We’re too concerned about fear, and not focused enough on the opportunity for personal growth. When you follow your heart, everything changes. Trust your intuition. Trust the universe. Stop asking everyone else what they think, and look to yourself and the universe. Look for the little things. Better yet, ask for a sign. It might be the glow of a sunset. Or a ladybug. Or a flower. You’ll find it. You deserve to live the life of your dreams.

3. Make your own rules

Don’t wait for approval – follow your intuition and do it. When we look at history, women ruled. We’ve become socialized to fit into a patriarchal society.  Every time I am told there is a rule or ‘ it’s always been this way’ I have a visceral reaction to it – why? Why does this exist? Who made it? 

where to stay

Find Your Own Adventures

As the CEO and Editor of JourneyWoman, Carolyn is a passionate advocate for women's travel and living the life of your dreams. She leads JourneyWoman's team of writers and chairs the JourneyWoman Women's Advisory Council and Women's Speaker's Bureau. She has been featured in the New York Times, Toronto Star and Zoomer as a solo travel expert, and speaks at women's travel conferences around the world. In March 2023, she was named one of the most influential women in travel by TravelPulse and was the recipient of a SATW travel writing award in September 2023. She is the chair of the Canadian chapter of the Society of American Travel Writers (SATW), a member Women's Travel Leaders and a Herald for the Transformational Travel Council (TTC). Sometimes she sleeps. A bit.


  1. Jasmine Thompson

    Carolyn, I wanted to share this with you. I first followed the writings of Evelyn Hanson ‘s travels and now I have been enjoying your reflection of your travels around the world.
    I admire your enthusiasm & courage in making such a drastic life change in living the life of your dreams. I am 73 yrs old, married 48 yrs with 3 adult children. I have often thought, if my life panned out to be different & living independently, I would have most certainly reached out to living a life of travel. But my life went in a different direction and so instead, I have the fortune of being able to experience travel through your shared articles.
    Thank you for sharing a little bit of your personal life and your experiences as you travel around the world, Merry Christmas and only the best to come in the New Year. Jasmine Thompson

  2. Gretchen

    Carolyn, I have enjoyed following Journeywoman these last several years and have started trying to provide my insights daily in responses from nearly 30 years of working from home, many years of living abroad before that in Germany, France and Brazil, and being a digital nomad since 2007, now living 7 to 9 months abroad, in four base countries each year, and the rest split between my home I own free and clear in Redlands, California and a long-time friends place in the Bay Area, with him. Made my art/research businesses that are based in Texas virtual and share with my sister if I do work there in person. It is an amazing journey.

    This year is a transition year to move from doing research and art for a living for clients, to writing and my own travel memoirs art and other projects full time so have to figure how to generate the most passive income.
    I find owning a property that is a comfortable home for me in the USA, but a home away from home for others, such as travel nurses, visiting professors, grandparents, people testing area for purchase and fellow digital nomads has generated much of my travel monies, or at least lodging abroad $us21-24k per year, Key though are the property managers…and I found a nearby husband wife combo to handle check ins, cleaning, repairs etc. I only rent minimum one month and have an Italian couple for the last 4 years renting 9 months a year! But we split in two so I am now a superhost on Airbnb, which helps in finding tenants during summer months when they live in Italy. I kick them out every other year at Christmas too so I can spend in my home in Redlands near family in Long Beach, California!
    I automate all my bills!

    Would love to finally meet up with you and other journeywomen sometime. We always seem to just miss each other, whether London or Florence, Slovenia or Spain! This year I will be in Cairo in Feb-March 5 weeks; Warsaw April-May 7 weeks; Mostar, Bosnia 2 months July-August; and Sevilla 2 months September-October. I have an extra bedroom in all places…last year for that…will likely stay in studios once living on social security, rental income and any passive income from book sales!
    Here’s to journeywomen everywhere!
    Thanks again for all that you do!


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