For more than 15 years, Shari Winchester has been telling stories visually.
As a graphic designer by training, she has built a solid, 15-year career in graphic design and also expanded her creativity organically into fashion and costume design, where she has spent the last decade bringing characters and concepts to life. Winchester is also a wife and mother of two, roles that, like her work, demand her energy, devoted presence and constant care. A lover of colour, texture and travel, her creative journey places vibrance and evolution at the core, and she has recently taken her talents into a new field with the creation of her self-care journal, Rooted.
Rooted came into being parallel to Winchester’s personal and professional growth, where she struggled with the challenging weight that many women know well. She was carrying multiple roles without pause, moving from task to task, rarely stopping to check in with herself. A turning point came in July 2025, when she travelled to China for a seminar. Alongside another working mother, they were both juggling Trinidad-based jobs, checking in with their families and attending the day-to-day events of the programme abroad. The experience raised a mirror to herself, and she saw the reality of how much Caribbean women often carry - professionally, and personally - without ever fully stopping. Upon her return home, she came to the realisation that she was deeply burnt out. Exhausted in body and spirit, she realised that she had something to give.
The journal that would become Rooted began as a personal lifeline. Writing and designing the journal was a passion project and an outlet, a quiet space where she could process her burnout and begin to breathe again. “Women don’t have space for ourselves,” she realised, “especially Caribbean women, who often feel guilt around resting or treating themselves well.” The cultural inheritance of “always doing” became apparent to her. The burnout she was feeling could be traced back generations, remembering the ways her grandmother, who served endlessly, never stopped, and saw in herself that even moments of rest were accompanied by self-criticism.
Rooted was thus born from a simple desire to help herself and, by extension, help Caribbean women pause. Winchester wanted to create something “by us, for us, that was familiar and comforting, something Caribbean in spirit, encompassing the values we hold dear, and ultimately still honest, warm and grounded.”
“I created Rooted because I know what it feels like to carry so much that you forget yourself,” she said. The journal honours culture, memory, evolution and emotion, offering a companion for moments when women want to slow down, listen to their innermost thoughts and find peace in who they are becoming.
True to her entrepreneurial spirit, Winchester decided to publish the journal and share it with others. Using her graphic design skills, she designed and illustrated the entire book herself, despite not considering herself an illustrator. It became an exciting new creative challenge. From scratch, Rooted was written, designed, manufactured and published locally in only five months, and she brought it to life in December 2025.
The journal is structured into six chapters, each with thoughtful prompts such as Where is my safe space? And what makes me feel appreciated? It also includes reflective quotes, conclusions for each chapter, and colouring pages that invite calm and play. One quote that resonates deeply with Winchester reads: “Joy is not in things, it is in us;” and “stillness is where clarity begins.” For her, Rooted filled a space that didn’t exist with a goal to reframe and unlearn “generations of negative self-talk,” replacing it with gentle affirmations.
While Winchester admitted that even through this process of healing her burnout, she hasn’t mastered the balance between rest and responsibility, she knows its importance. The physical manifestation of stress over the past year made that clear. Even cherishing the precious small moments where she wakes up early to sit quietly by herself, or simply being still have become acts of self-preservation. “If we [as the women in the household] are not okay, neither is anyone,” she said, a nod to the metaphor of putting on your oxygen mask before others.
Receiving an overwhelmingly positive and grateful response from women who said the journal is exactly what they needed has been deeply healing, Winchester said. She feels that Rooted fills a long-empty space. However, one of the most meaningful moments of feedback came close to home. As she wrapped up the book, her 15-year-old daughter, a student at Holy Name Convent, watched in awe as the process unfolded, from concept to completion. At the launch, she told her mother how proud she was and excitedly shared the journal with her friends and their mothers. For Winchester, this moment was not only a proud one for her, but cemented the importance of modelling rest, creativity and self-worth for the next generation.
Looking ahead, Winchester envisions Rooted as more than a journal. She is planning to create spaces and places for women to actively use the journal and build community amongst themselves. Ever buoyed by her entrepreneurial spirit, she also wants to expand the journal’s reach, taking it throughout the Caribbean and into the diaspora. Though she once worried her focus might have been too niche, she is now assured that the uniqueness of the Caribbean woman’s experience is enough to carry the journal forward.
Rooted is Shari Winchester’s love letter to women like herself, women who deserve gentleness, community and the freedom to finally rest.
Rooted can be ordered on the website (https://neonness.co/journal) or purchased at 36 Cornelio, and will be available internationally via Amazon soon.
