Falling in love is a risk. But what happens when your love is so unconventional it threatens your career and reputation? Here’s my profile feature in CanvasRebel, and how RISK created triumph (when I allowed myself to ‘fail’ in order to win). #profilefeature #interview #risk
I feel honored to have been chosen for this profile feature in CanvasRebel Magazine. I’m often asked about my origin story in terms of how I found my way to this industry. I’ve had scores of interviews that focus on how falling in love with a younger man brought me into the work I do today. So I especially appreciate this angle of presentation, as it focuses on risk.
In order to love, we have to be willing to bring our best selves forward. And we have to enter the construct of love understanding that it brings both joy and pain, as well as triumph and failure. We must risk the downside in order to participate in the upside.
This article is rather lengthy so I will be including several sections that might be new to you. I encourage you to click the read more to gain access to the entire content of my conversation.
The Editor writes, “We recently connected with Susan Winter and have shared our conversation below.
Editor: Susan, thanks for taking the time to share your stories with us today Can you open up about a risk you’ve taken – what it was like taking that risk, why you took the risk and how it turned out?
Taking a Risk:
Susan: “Risk comes in many forms—stepping into a competitive field, investing savings into a startup, or the unexpected risk of falling in love. The last one became my story.
Falling in love is a risk. It’s a straight up gamble with no guarantees. But what happens when your love is so unconventional it threatens your career and reputation? Most would walk away. I didn’t.
I arrived in New York City as an Opera singer and stage actress. The work thrilled me. The lifestyle didn’t. Over seven years, I transitioned to becoming a Corporate Spokesperson for over half of the Fortune 500 companies. That career led to becoming the host and moderator of ‘Corporate Profiles’ on Financial News Network (FNN), now called CNBC. The work was exciting and the respect fulfilling.
With my career came societal expectations about my romantic choices. People assumed I’d choose someone polished, cosmopolitan, and age appropriate. But when I built my dream home in a rural location an hour from Manhattan, my life quickly changed.
Suddenly living outside of the cosmopolitan New York City environment, I was exposed to a limited dating pool. Yet, it was there that I met a wonderful younger man in the local gym with whom I had great conversations. He was bright, ambitious, and a deep thinker. I had no idea that he would become my partner a year later and would mark the great love in my life.
In 1995, in a remote town, a relationship with someone 20 years younger was unthinkable—even to me. But when something feels true and right, you know it.
This wasn’t Manhattan, and I had no allies. As a newcomer from the big city, I sparked a storm of gossip and controversy. Invitations to community events dried up, and friends—both new and old—distanced themselves. Some women openly admitted their husbands forbade them from seeing me.
As rumors snowballed, so did the consequences. I was branded a “witch” and a “spellcaster.” Simple errands like getting gas or groceries became battles, with attendants sometimes refusing to serve me. My TV show on spirituality and higher consciousness, ‘Higher Ground,’ was pulled from the local network after over 100 residents signed a petition labeling me a “detriment to the community.”
That’s a long fall from being a highly respected business professional. But in that time and place— it was my reality. I could have capitulated. I could have given up. I could have dumped my boyfriend and been gradually accepted back into the group. But this was not a group from whom I wanted acceptance. And moreover, there was a greater conversation to be had.
I believe that Life is beautiful and purposeful in its events. Nothing comes here to torture us, only to advance us. And in the midst of all this drama and trauma, I held steadfast to that knowledge. It was a casual comment by a friend that enabled me to activate the greater gift within all of this pain. She suggested writing a book about older women and younger men.
That book became an international bestseller. ‘Older Women/Younger Men; New Options for Love and Romance’ (New Horizon Press, 2000) is still considered the ‘bible’ for older women and the younger men who love them. I interviewed over 200 couples who had similar stories to mine. Formerly ostracized, they now had a voice. Formerly misunderstood, they now brought forth a greater understanding of inclusion and opportunities for love.
The media attention I gained allowed me to uncover a new and unexpected career; that of Relationship Expert— a title given to me by ‘The Today Show.’
I didn’t anticipate being in this field as it didn’t exist at that time. And though I was one of the first, hundreds of others have since entered the dating and relationship realm. To date, I’ve counseled over 6000 individuals. As of this interview, I have over 42 million views on YouTube, and 1250+ interviews by top-tier newspapers, magazines, TV, Radio, and Podcasts.
I had no idea that I would discover my true calling by taking the risk of falling in love. This type of risk isn’t associated with career success. And I had no idea that in the midst of all the tears and pain, I was actually on the correct path to discovering my greatest contribution and deepest happiness.
Here’s the twist. We rarely understand the process as it’s happening—its purpose is obscured by uncertainty.
To be sure, some risks aren’t worth taking. They’re a known dead end. But some risks “pull” at us, compelling us forward despite every outward sign to stop. It’s in those moments, when we’re driven by something we can’t yet name, that we’re honoring an inner truth—still forming, not yet born, but quietly coming into fruition.”
Editor: Let’s talk about resilience next – do you have a story you can share with us?
Susan: Starting a new career later in life demands a unique kind of resilience. It’s not just about forging ahead, staying disciplined, or maintaining momentum—it’s about being willing to start at the bottom and climb back up. For those who’ve reached the peak of their former careers, it’s a daunting task to be a beginner again.
Editor: What’s a lesson you had to unlearn and what’s the backstory?
Susan: “I had to unlearn the desire for social approval. Being at the center of controversy isn’t easy, but it’s far better endured when you’re fighting for a greater cause. The cause was beyond older women and younger men. It was about a woman’s worth—beyond youth and beauty. And the ability to be seen in totality, with inherent value that’s undiminished by time.
I prefer to be liked, as we all do. I prefer to be respected. What I never expected was the admiration and respect that came from being true to myself and my beliefs. But by playing the wildcard and trusting my gut, I found the ultimate form of guidance, and acceptance.”
