Naomi Weisman is a Canadian-Australian and mother of three who loves to Ramble with her dog, cook for family and friends, and laugh whenever possible.
Is it just me, or did our generation of women lack ambitious direction?
Yes… I think it’s just me.
When I was a kid, I never knew what I wanted to do with my life. Marriage and children weren’t some grand aspiration of mine; I simply assumed they would happen eventually.
The one thing I did know—without question—was that I wanted to travel the world. My parents were avid travellers and extraordinary storytellers. They spoke of going to communist Russia in 1972 to watch Team Canada face the Soviets in that iconic battle for hockey supremacy, or hiking in Argentina to see Iguazú Falls. Their stories planted something deep in me.
So while many of my friends were entering the workforce or heading off to university, I was backpacking through Europe, living on a kibbutz in Israel, or riding a camel around the pyramids in Egypt. I felt that the rest of life’s responsibilities could wait.
When I eventually returned home, I fell into a career in retail, which evolved into management and then into a buyer for a women's fashion house. I enjoyed the work, but I wouldn’t describe it as a passion.
My parents always insisted I had a mind suited for academia. I never believed them. I didn’t see myself as particularly intellectual, and I was comfortable with the fact that I wasn’t university-educated.
I met my husband through a friend when I was twenty-five—my very first blind date. I was never much of a dater; my only other relationships had been in high school or on the kibbutz, where friendship came first.
After we married, I continued working, but when we had our first child, my husband wanted me to stay home. His job was demanding, and given my lack of clear career ambition, I agreed. I was content raising our children and managing our home.
Then came separation and divorce at forty. I had three children aged ten and under, a house to sell, and a mother with advanced Parkinson’s and Alzheimer’s. I felt unmoored—panicked, uncertain, and deeply afraid.
My father, always my sounding board and my steady harbour, said to me, Go to school, Naomi. He told me I had a curiosity about the world and untapped talents I had never fully claimed. I couldn’t see myself that way, but I trusted his vision of me more than my own.
It took enormous courage to apply. I was convinced no university would accept a woman with my background and perceived limitations into something as lofty as higher education.
As for what to study, the answer revealed itself naturally. I had always been a reader, fascinated by language and meaning. I loved historical fiction and literary classics—Dickens, Austen, the Brontë sisters. So I chose a double major in English Literature and History, because I simply couldn’t choose between them.
Five years later, I earned my honours degree and became a teacher at forty-six. I taught English until the pandemic arrived, and I realized that teaching online was not for me. The learning curve felt too steep, too technical, and I knew—honestly—that I would not be happy or at my best doing it.
Then came Sole Sister Ramblers.
My friends have dragged me—often kicking and screaming—into the twenty-first-century tech world. I can hardly believe what I have learned over the past four years while helping to build this community. Jill Thomas, in particular, has patiently held my hand, taken deep breaths, and explained how to do the same thing in the backend of the newsletter more times than I care to admit. And somehow, after much angst, I now know how to do it.
So why am I telling you all of this?
Over the past four years, I have met countless Sole Sisters—women in midlife and beyond—who are thoughtful, accomplished, and deeply intelligent. Women who have taken winding, unexpected paths to arrive where they are now. Mothers, writers, entrepreneurs, teachers, doctors, lawyers, activists, and women who have endured loss, reinvention, and profound change.
What strikes me most is how few of us travelled a straight line to get here. So many of the women I’ve met through Sole Sister Ramblers have lived several lives already. Careers paused and resumed. Dreams deferred, reshaped, or quietly revived. Detours taken not out of indecision, but out of necessity, love, responsibility, or survival.
These circuitous routes are not signs of failure or lack of direction. They are evidence of resilience, adaptability, and courage. They tell a story of women who responded to the realities of their lives with grace, pragmatism, and strength—even when the destination was unclear.
Lately, I’ve been reflecting on how often we fail to recognize our own potential until someone else mirrors it back to us. How sometimes all it takes is a community, a conversation, or a well-timed nudge to help us see ourselves differently—and to take the leap we didn’t know we were ready for.
I no longer believe that I lacked ambition. I believe my ambition simply took its time finding its shape. And when I look around at the women in this community, I see that I am far from alone.
If there is one thing I know now, it is this: there is no single path to becoming who we are meant to be. Sometimes the long way around is not a delay at all—but the very road that makes us ready.
READ MORE > Her Story, Rambler Cafe Blog
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