We caught up with the brilliant and insightful Winslow Vail a few weeks ago and have shared our conversation below.
Alright, Winslow thanks for taking the time to share your stories and insights with us today. We’d love to have you retell us the story behind how you came up with the idea for your business, I think our audience would really enjoy hearing the backstory.
As a child, I loved the fairies. Every day, I spent hours outside tending a fairy house I built beneath a large oak tree using sticks, moss, leaves, flowers, mud, and treasures from nature. I spent hundreds of hours working on my fairy house. At the same time, I wrote letters to the fairies, leaving the notes on my windowsill. The fairy world represented a safe space of love, validation, and joy, and I always confided in the fairies, sharing my deepest secrets, worries, fears, and questions about the world. Even as I entered second and third grade, fairy letters were the place where I felt safest telling my inner truth.
I was a deeply sensitive child who experienced anxiety and insecurity. I worked hard to please others, avoided conflict at all costs, and often felt overwhelmed by other people’s pain and suffering. The world felt loud and sharp, and I didn’t yet have the language or tools to navigate family, friends, or school confidently. The fairies, whether imagined or something more, offered me a sanctuary and an emotional lifeline to inner peace and soothing.
After college, I spent over a decade working closely with children and families in the United States, the Dominican Republic, Mexico, Chile, Canada, India, and Honduras. Across cultures and contexts, my work consistently focused on personal growth, resilience, creative learning, and empowerment. Again and again, I met children who reminded me of my younger self. They were energetically and emotionally sensitive, perceptive, emotionally attuned, and often overwhelmed by the world around them. I began to see a clear, consistent pattern: that highly sensitive children desperately need safe, imaginative, creative, and joyful spaces where they can explore their inner worlds, build emotional competence, and develop tools to foster confidence, calm, and inner connection.
In 2020, I began running my own Fairy School groups for children. As part of these gatherings, I started leaving handwritten notes from the fairies. The response was immediate and unmistakable. The children were captivated. They listened to the fairies in a way they didn’t always listen to adults. On the rare occasions I forgot to leave a fairy note, the children were genuinely devastated. That reaction reminded me of “the power of the fairies” and how children gravitate towards wonder, magic, and awe. The fairy messages landed in their hearts.
Through the voice of the fairies, children absorbed ideas about self-love, inner peace, emotional awareness, and resilience with openness and joy. Concepts that might feel heavy, abstract, or instructional became accessible, playful, and deeply embodied when offered through magic and imagination. This was the moment the idea crystallized. I began writing Fairy School letters to children, mailing them worldwide. Each hand-illustrated, double-sided letter contains gentle, empowering practices designed to support emotional competence, confidence, and calm.
Fairy School was born from the realization that what supported me as a sensitive child could support others, too, especially in a world where highly sensitive children are increasingly overstimulated, pressured, and disconnected from their inner lives. Fairy School fills this gap by offering an imaginative approach grounded in energetic and emotional tools that teach highly sensitive children to trust their sensitivity as a strength and to navigate the world with confidence, resilience, and joy. Fairy School is unique because it teaches emotional resilience and self-love to highly sensitive children through imagination, play, and personalized guidance from the fairies, delivered through in-person and online classes, fairy letters, a fairy podcast, summer camps, one-on-one sessions, and more.
As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?
I’m Winslow Vail Brokaw, founder of Fairy School, where highly sensitive children develop calm, confidence, and emotional resilience through imagination, creative practices, and energetic and emotional tools. My journey began in childhood, tending fairy houses and writing letters to the fairies, who were my safe space for sharing fears, worries, and dreams. That imaginative connection became a source of comfort, joy, and inner regulation, shaping my lifelong passion for supporting sensitive children.
Growing up, I lacked the tools to navigate school, friendships, and family with confidence. I often felt anxious, overwhelmed, and burdened by others’ emotions. At 17, I had my first energetic and emotional coaching session with Aleya Dao, a master sound healer, energetic practitioner, and Founder of the 7 Cups of Consciousness. Aleya taught me simple yet powerful tools to cultivate self-worth, calm, and joy internally. These tools became my trusty anchor, helping me navigate life’s ups and downs. I still use these tools today, and I wish I could have learned them as a child.
After college, I spent over a decade working with children and families across the U.S., Latin America, Canada, India, and Honduras. I noticed a clear pattern: highly sensitive children often feel overwhelmed, lack effective tools, and rarely have environments that honor their unique needs. This inspired me to create Fairy School in 2020, offering letters from the fairies, guided practices, small-group classes, and one-on-one sessions. These experiences encourage self-love, emotional awareness, inner peace, creativity, imagination, and a love of nature, all delivered via the joy and magic of the fairies.
Being sensitive can be challenging, and highly sensitive children often experience emotions more intensely, notice subtle details others might miss, and are deeply affected by their surroundings. Without the right tools, anxiety, insomnia, headaches, or overwhelm can be constant. Fairy School fills this gap by providing energetic and emotional tools in a safe, joyful context, helping children ages 4-20 to trust their sensitivity as a strength and build calm, confidence, resilience, and joy.
What sets Fairy School apart is the combination of personal experience, decades of study with master teachers, and a playful, imaginative approach that meets children where they are. I’m most proud of witnessing children light up while reading a fairy letter, sharing their dreams, and discovering strategies to navigate life with confidence. For families, clients, and followers, I want them to know that Fairy School is a nurturing, supportive, and magical space where highly sensitive children can thrive, feel seen, and embrace their feelings while cultivating joy, wonder, and self-trust.
Can you tell us about what’s worked well for you in terms of growing your clientele?
Fairy School is really growing one child and parent at a time. Each experience, whether it’s a class, a Fairy School letter, or an episode of the podcast, is designed to create a meaningful, heart-centered connection. I’ve found that the best way for new families to discover Fairy School is through word-of-mouth. When a child or parent experiences the magic and support firsthand, they naturally share it with friends, and that’s often how the community grows. It’s slow, intentional, and deeply rewarding. Every new connection builds on a foundation of trust and care, and that’s what makes this growth feel so authentic and special. It also requires patience and perseverance.
One story that illustrates my resilience is really woven into my everyday life as a highly sensitive person. Growing up, I often felt overwhelmed by my own emotions and the intensity of the world around me. I experienced anxiety, insecurity, and the weight of other people’s feelings as if they were my own. Over time, I learned (and continue to practice) tools to navigate this sensitivity, including emotional validation known as “affect labeling” and emotional and energetic skill sets that I have spent decades studying.
The same tools I now teach at Fairy School are the ones I rely on every day. I use them to stay calm, centered, and connected to my own inner world. This personal practice has not only helped me manage my sensitivity but has also given me the confidence to create Fairy School as a space where children can learn to trust their own sensitivity, navigate challenges, and cultivate resilience. It’s deeply rewarding to know that the methods I use to take care of myself are helping children feel empowered and supported in the same way.
Contact Info:
- Website: https://www.winslowvail.com/
- Instagram: https://www.instagram.com/winslowvail/
- Facebook: https://www.facebook.com/winslowvail
- Youtube: https://www.youtube.com/@winslowvail
- Other: The Fairy Podcast: https://www.buzzsprout.com/2512803
Image Credits
Sunflower Fairy Letter – Halsey Pierce