Parenting Circle: The Inner Life of Parenting with Deepa Gupta
Parenting Circle @ The OTR Academy Club
Parenting Circle @ The OTR Academy Club
The purpose of Parenting Circle @ The OTR Academy Club is to empower our community of parents to share and learn new coping skills, develop new resources and tools, reframe challenges and create a safe space to come together in small group settings – to connect with other parents, share parenting challenges, support each other by sharing experiences, resources, and practices, to exercise self-care and wellbeing practices together.
This is a space where a community is forged – together we co-create solutions and celebrate positive change no matter how small. Each participant is responsible for their own learning through active participation and sharing: to explore solutions together and help each other deal with parenting challenges in the digital age – supporting each other to better prepare our children/child to meet an increasingly uncertain New Future.
Our goal is to integrate child-centred conversations, self-awareness and inner work into these circles, while staying true to our mission of fostering genuine family wellbeing beyond mere parenting techniques. This is a space for the community by the community – facilitated by wellbeing practitioners, parenting coaches and professionals – those who are passionate about nurturing healthy, positive parent–child relationships and the development of future-ready children.
Series Theme: The Inner Life of Parenting – Understanding the Person We Become in the Process
Session 1: Seeing through your child’s eye. | Understanding their inner world
Date: Wednesday, 5 August 2026
Time: 8PM - 9PM
Mode: Online via Zoom
Session Goals: Parents reflect on their growing up emotional needs, recognise their child’s needs beneath behaviour, and respond with deeper understanding and awareness.
Session 2: Becoming themselves. | Understanding development and identity
Date: Wednesday, 12 August 2026
Time: 8PM - 9PM
Mode: Online via Zoom
Session Goals: Parents understand the developmental changes shaping their child’s identity and autonomy, while reflecting on the self-talk influencing their parenting responses.
Session 3: The space between us. | Understanding the relationship dynamics
Date: Wednesday, 19 August 2026
Time: 8PM - 9PM
Mode: Online via Zoom
Session Goals: Parents will assimilate their reflections and learnings about themselves and their child’s emotional needs, putting them into practice through connection tools that deepen the relationship.
Deepa Gupta
Founder of RAEwithDeepa Pte Ltd | Certified ICF Transformational Coach
Deepa is dedicated to empowering parents and young adults in Singapore and beyond. Her parenting journey began in New Delhi as a banking professional and mother, where she realized that meeting her child’s needs wasn’t enough — a deeper emotional connection was missing. Relocating to Hong Kong without the support of family or community deepened this realization, prompting her to pursue executive and life coaching. Applying these tools at home transformed her relationship with her son from control to friendship and mutual respect.
Deepa now advocates for a progressive shift in parenting: task-based, hierarchical parenting to nurturing resilient, independent children through strong emotional bonds. She works with parents, young adults, and community groups, fostering self-awareness, confidence, and positive transformation through interactive coaching and mentoring.
Passionate about building supportive ecosystems, Deepa believes community support is more vital than ever in today’s fast-paced world. Guided by the philosophy that “it takes a village to raise a child,” she equips parents with the tools to foster emotional intelligence and meaningful family connections.
For Deepa, listening to your child is a gift.
About the OTR Academy Club
The OTR Academy Club is created as a branded community space of the OTR Academy where wellbeing practitioners, volunteers and the public can continue personal and professional growth with holistic wellbeing as the overarching theme — through ongoing events, peer support circles, and workshops. The structure is flexible, allowing for multiple thematic circles (e.g., for parents, teachers, career, etc), and emphasizes shared learning, applications, and the development of practical wellbeing skills. We want to create an environment where each group has a clear structure and a safe space for both practice and peer learning.
Our circles revolve around four main themes:
DEVELOP: Personal development through understanding ourselves — our strengths and blind spots — in order to continue growing with clarity and purpose.
CONNECT: Mastering the science and art of communicating with compassion so that we thrive in the relationships that matter.
LEAD: Level up leadership skill sets with focus on leading with purpose and connection in the age of AI.
BELONG: Bringing community and collaboration to the forefront by sharing access to a large network of professional mentors, social impact leaders, mental health practitioners and experts.
Our purpose is to inspire individuals in their personal and professional development journeys and foster deeper connections. Through deep sharing and guided reflections, attendees will learn how to thrive through stories, tools and strategies, as we work together and support each other as a community in our move towards a holistic transformation.