What If and Why Not? A Mantra for Living with Curiosity and Courage with Bobbi Brown

In this episode, Bobbi Brown explores the questions “What if?” and “Why not?”—her mantra for living with curiosity and courage. Renowned makeup artist, entrepreneur, and founder of Jones Road, Bobbi shares how choosing decency over drama and normalcy over fabulosity shaped both her career and her life. She talks about the power of kindness, the myth of “always-on” authenticity, and how the outside—our clothes, lighting, and even a touch of makeup—can support the inside without replacing it. The conversation also delves into bio-individuality in health, the art of reinvention, and why making small choices, day by day, adds up to resilience and joy.

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Key Takeaways:

• Bobbi’s life and career journey as a makeup artist and entrepreneur.
• The importance of kindness and authenticity in personal and professional life.
• The concept of normalcy versus fabulosity and its impact on self-acceptance.
• Bobbi’s approach to makeup, focusing on enhancing natural beauty rather than drastic changes.
• Transition from the beauty industry to becoming a functional health coach and the idea of bio-individuality in health and diet.
• The significance of flexibility and self-compassion in health and lifestyle choices.
• The role of naivety in fostering creativity and resilience in pursuing new ideas.
• The emotional complexities of leaving a successful business and navigating new beginnings.
• The influence of family dynamics and personal history on self-identity and growth.
• The pursuit of joy and authenticity in life, including personal interests and passions.

If you enjoyed this conversation with Bobbi Brown, check out these other episodes:

From Toxic Perfection to Honest Care: Boundaries, Healing, and Wholeness with Sophia Bush

Living Skillfully with Gretchen Rubin

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