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.

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.

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.

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? 

Find Your Own Adventures