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

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

By Carolyn Ray, JourneyWoman

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 placees 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 that I loved, looked around its overflowing rooms, and decided it was time to make a 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.