Liberation & Freedom | Sylvia Winter

Liberation Freedom | Sylvia Winter

Sylvia Winter


It’s always risky to pigeonhole extremely creative people—they’ve got more than one trick up their sleeve. In the case of Founder and Creative Director Sylvia Winter, those tricks also happen to include pilot, a podcaster with thousands of listeners, landscape designer, artist, runner, skier, mother, and more. She has always believed in the unique strengths of the multi-hyphenate: one with several professions or skills.

She founded When Women Fly as the virtual space she needed and couldn’t find in the early spring of COVID 2020. During a time that shut down the world as we knew it, she strongly desired to tap into her perennial fascination with the metaphor of flight and female power. 

She wanted to hear stories of women, by women, who were changing the world through their bold, rigorous, and unstoppable physical strength and mental tenacity. It was always looking beyond the accomplishments to examine the underpinning of women who “fly” and explore the phenomena of what happens when women fly.

In When Women Fly, Sylvia believes that every woman harbors the spirit of flight, and what determines whether you climb the mountain, cross the finish line, fly the plane, or dare to dream the big idea is tethered to unlocking confidence and validating female power. She believes that women get the opportunity to define themselves despite a society that is tempted to shape them into roles and create an “ideal.” She hopes that by hearing women tell their stories of passion and perseverance, others can dive deeper into their own.

Sylvia is clear in her vision for women to feel the liberation and freedom inherent in flight. She began flying to get a new perspective on the ground and the patterns in the landscape, but it soon became more than a tool and has been a way to build durable resilience, grit, and discipline that is transferable way beyond the physical act of flying or lifting off. The liberation, thrill, and excitement when we fly is indescribable. The sky is not the limit – it’s just the view.

Sylvia also brings a keen awareness fear. “Not one of us goes through life unafraid. Fear is normal, but it can shrink the world if you let it,” says Sylvia, who does not let fear stop her from what she wants to do and how she is called to show up. It comes out in the founding of When Women Fly as a podcast – making a debut into an entirely new creative medium. “There are no guarantees but there are too many amazing things to experience to ever let fear hold us back,” says Sylvia. “Acknowledge fear and encourage yourself to do it anyway. It takes practice and repetition.”

A True Leader

When Women Fly has an extensive network of women charting new territory in male-dominated fields, by amplifying these voices, female entrepreneurs can see examples of what is possible. They are planning several workshops over the next year led by Sylvia that explore how learning to fly as a metaphor can be translated into actionable steps toward doing the things women thought they couldn’t do.

Women are looking for ways to unlock confidence in their lives and take the controls into their own hands. Sylvia supports women by being a steady guide and sounding board, interviewing women who serve as motivation to others out there trying to establish themselves, and mentoring women with backgrounds in art and science who don’t fit the mold. Many know what it’s like to “fly” and need the support to get started and stick with it.

According to Sylvia, leadership is building people up, not tearing each other down. “We inspire, support and validate over and over again. The results are unlocking wellsprings of confidence. The women of When Women Fly are intelligent and clever, talented, and strong – and they know it,” she explains. “We are confident. This offers hope – hope that gender inequities will dissolve as the next generation grows.” Sylvia features confident and brave women and admits to being bit wild herself. “To be wild is to be full of life, ideas, and color- unapologetically so. Ultimately being wild is being free. Free to try new things without self-judgment.”

The movement – celebrating flight as a symbol of freedom – when women fly offers a vision that transcends the physical. Change in culture starts with inner change. “I believe that when we tell our stories, own our fears and dismantle our perceived limitations – the possibilities are boundless.” Sylvia uses in the episode intros. Sylvia and When Women Fly apply the principles of movement and flight, to self-improvement, business, and storytelling – and the ways we can level up in our lives.

Motivating Women

By avoiding the pull to become industry specific, When Women Fly has remained a project about how they approach what they do. Sylvia and her team think that although women are doing innumerable things today, there is an infinite catalog of women who have been the “only” and the “first” or who have just been so gritty and determined they cannot be ignored. “Women have many phases of life and the way in which we manifest the spirit of flight will look very different. We are fascinated in what happens when women fly because we know that this is reclaiming our power, independence, and authenticity,” adds the steadfast leader.

When Women Fly’s biggest achievement is their impact within their community and the audience, new and old, listeners have had life-changing moments in their lives triggered by When Women Fly. Beyond numbers and awards, this is by far the most important achievement to Sylvia and her team. “This means that we are not only creating a space that will support people in going for their dreams, but they are no longer settling for being a passenger in their own life. This is amazing,” she elucidates. “We want to celebrate women and girls for being themselves. In a world that favors conformity: acting a certain way, wearing the right clothes, fitting into predetermined roles, and behaving within a set of normal expectations – we want to highlight women who rewrite this code of conduct. It’s unfinished business and yet, I am so inspired by the swelling momentum of women who are redefining roles and expectations. Real change is happening and we are playing our part. My daughter – our daughters-  are grow

Sylvia Winter Award

" I believe that when we tell our stories, own our fears, and dismantle our perceived limitations - the possibilities are boundless. "

Sylvia Winter

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Liberation & Freedom | Sylvia Winter
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Liberation & Freedom | Sylvia Winter
In the case of Founder and Creative Director Sylvia Winter, those tricks also happen to include pilot,
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The Women Leaders
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