Why Women Hesitate to Apply and Program Outcomes

Simon and Chris analyze gender differences in applications, outcomes from mentorship seasons, and motivations for fame versus craft.

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In this episode, Chris Do sits down with entrepreneur and philanthropist Simon Squibb to explore the imbalance between talent and opportunity. Together, they discuss how people can break through systemic barriers, the importance of resilience in creative fields, and why access—not ability—often determines success.

They reflect on Simon’s viral “What’s Your Dream?” project, the lessons he’s learned from mentoring others, and how creative education can become more inclusive. If you’ve ever questioned how to turn your skills into real opportunities, this conversation delivers unfiltered clarity and practical wisdom.

Timestamps

(00:00) - Intro

(02:10) - The Real Tests of Resilience

(04:42) - Building a Personal Brand

(07:28) - Getting Paid Speaking Gigs

(10:15) - How Representation Creates Access

(13:09) - Mentoring Young Designers Online

(16:45) - Why Women Hesitate to Apply

(19:52) - Fame Over Craft Discussion

(23:17) - Creating a Creator Accelerator

(27:44) - How to Price Creative Work

(31:55) - Overcoming Imposter Syndrome