Happy Place How Trinny Woodall deals with rejection: Learning from failure and feedback
Jul 21, 2025
Trinny Woodall, entrepreneur and founder of Trinny London, candidly discusses her journey through rejection and resilience. She shares insights on backing one's ideas and the courage it takes to seek feedback without fear. Trinny opens up about personal challenges, including her time in rehab and the impact of grief on her life. The conversation dives into the importance of self-worth and personal presentation, as well as the unique challenges faced by women in business, offering listeners both inspiration and practical strategies for growth.
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Self-Worth vs Trust in Life
- Trinny separates personal self-worth from work-related trust when dealing with challenges.
- Personal doubts stem from self-worth, while work doubts arise from trust in decisions and teams.
Early Business Failure and Intuition
- Trinny raised money during the dot-com boom but had to close her first business after two years due to inexperience and market challenges.
- She learned to trust her intuition more when founding Trinny London instead of hiring top executives too early.
Persistence Amid Rejection
- Trinny faced repeated investor rejections but sustained belief in her idea like persisting through IVF struggles.
- She stayed in a 'keep it going space' of cautious optimism to ultimately succeed.