Meet Carolyn Ray: Reinventing What Matters

If you’ve ever wondered what it would be like to sell everything you own—your home, your car, and most of your belongings—so that you could refocus your life around the people and work that matter to you, Carolyn’s story is one you’ll want to read.

Carolyn Ray has always been dedicated to her work and the impact it can make, setting a strong example for her daughter as a single, career-driven mother, and an entrepreneur. After spending 10 years at Interbrand, most recently as the Managing Director of its Canadian business, Carolyn left to start her own brand strategy firm, AUTHENTICA, in 2017. A year later, she decided to sell her home, her car, and 75% of her belongings. She’s since taken over JourneyWoman, the world’s first women’s travel website, which allows her to do more of the work she loves (travelling, writing, and empowering women) while spending more time with the people she loves.

We know Carolyn to be a driven, compassionate, and resilient woman. She’s purposeful with her time, energy, and money while maintaining a “let’s do it!” attitude towards life. We sat down with her to learn more about why she decided to sell everything, how that changed her outlook on money and consumerism, and her newest venture, JourneyWoman.

Why money isn’t her driving motivation

In addition to sitting on the Myseum of Toronto‘s Board of Directors, Carolyn feels fortunate to run two businesses she loves. You don’t have to spend much time with Carolyn to feel the care she has for the work she does, the people she works with, and the community she leads. Although extremely successful in her endeavours, it’s clear that she’s not guided by profit margins. “Everything I’ve done well has been because I truly cared,” she affirmed, “money has never been my motivation. The times I have made decisions for money, instead of choosing my values, I was desperately unhappy.”

Why she decided to sell everything

When her daughter, Alyx, went to university almost two years ago, Carolyn decided to make a big lifestyle change. She and Alyx had just returned from a transformative trip to Kenya with WE, and it became clear to Carolyn that she needed to live a simpler life. In the span of six weeks, she sold her house, returned her leased car, and auctioned most of her furniture. Alyx and Carolyn donated 90% of their clothes. Carolyn says they did everything possible to rid themselves of material things—hiring an auctioneer, hosting garage sales, giving furniture to friends, and donating whatever they could to charity.

Carolyn ended up with one 10’ x 10’ storage unit to keep some beloved antique furniture, family heirlooms and musical instruments, including a piano her great-grandfather made in Toronto. Everything else fit in a small moving truck she drove herself.

Why she opted out of homeownership

After selling her house, Carolyn had to decide if she wanted to buy again or rent. Reflecting on 30 years of trying to balance being a good mother and employee with a good credit rating, she asked herself why she would want to go back into debt or have the ties that come with homeownership.

“For most of my life, my focus was about managing debt, which is very stressful.” Carolyn reflected, “I had an RRSP from the time I started working in my 20s, I saved, only had one credit card, never missed a mortgage payment, and had an RESP for my daughter. I did all the things I was supposed to do but I was constantly stressed out about money. After having houses, a cottage, boats, and cars throughout my life, I just wanted to be free.”

Having the flexibility to live wherever she wanted was important. When her partner left his job in New York and moved to Canada, they decided to rent a furnished condo downtown as a short-term measure. Now they’re focused on living a simple life without a lot of possessions and can choose to live anywhere in the world.

How her view of consumerism has changed

We all know how easy it is to find ourselves spending more time or money trying to find the ‘right’ things to wear or put in our house. “We’re trained to acquire material possessions,” says Carolyn, “it takes a while to unravel that.”

“All the things I spent hours and months looking for…” Carolyn began, “what a waste of time. I could have been spending that time with my daughter, or writing, or exercising. Instead, I was going from store to store, looking for that perfect lawn set.”

Now, Carolyn finds life simpler and easier when she doesn’t have a list of things to acquire and look after. She likes the feeling of being able to put things in a backpack and go.

How she’s redefined the meaning of home

Like many of us, Carolyn’s relationship with money has changed over time. “It’s a means,” she shares, “money is important to me, just as a home is important to me, but we can redefine it. I used to think home is where you have your belongings,” she remarked, “but home is where my family is. I don’t care where we’re living if we’re together. I don’t need all the artifacts. I am grateful I had this phase of my life, but now I just want to live freely with people that I care about.”

Why she’s excited to be JourneyWoman’s next CEO

Carolyn never expected that JourneyWoman would become a part of her life. Founded in 1994 by Evelyn Hannon, JourneyWoman is beloved by women travellers around the world. It inspires women to travel safely and well by connecting like-minded them in a global community. Before Evelyn passed away, her daughter, Erica Ehm, invited Carolyn to consider taking over the business. Together, they hired a third party to conduct an objective valuation to determine the value of the JourneyWoman brand and website. In July 2019, Carolyn bought the business and is now JourneyWoman’s CEO and Publisher.

Although not something she ever intended to do, a series of serendipitous events and the encouragement of Evelyn’s family made her feel called to do it. “It’s an honour to take on someone’s legacy but also a bit intimidating,” she says, “I see this as an opportunity to reinvent myself and pursue my passions of travel, empowering women and sharing their incredible stories of courage and resilience learned through travel.”

Seven months later, Carolyn and her team just re-launched JourneyWoman with a new brand, website, e-books, a line of accessories, and a series of virtual sessions to support the global community.

“I never imagined I would be re-launching a travel business in the midst of a global pandemic, but it has opened up all kinds of new conversations and opportunities to strengthen our community,” she shares. “We are more than a website, we are a platform to empower women, with travel as a shared passion.”

Well said, Carolyn! Thanks for speaking with us and sharing your passion for reinvention, it’s truly inspiring. I’m sure all of us are looking forward to a world we can get out and explore safely again!

To learn more about JourneyWoman, please visit their website and Facebook page or follow them on Twitter or Instagram.

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