Underdog Mentality and Skill Stacking

Jess Wiseman is a multidisciplinary artist and creative director known for her storytelling, design, and her raw, honest reflections on the creative journey. In this episode, Jess opens up about fear, identity, burnout, obsession, comparison, reinvention, and how she built a career by posting consistently, experimenting publicly, and rebuilding herself from the inside out.

We go deep on creativity, psychology, filmmaking, social media, AI, discipline, and the hidden struggles behind “overnight success.” Jess shares the real cost of chasing perfection, how comparison destroys confidence, and why intention matters more than obsessing over tools or trends. She also breaks down how she got clients without experience, how she survived burnout, and the small habits that completely transformed her career.

Whether you’re an artist, filmmaker, designer, or creator trying to navigate the modern creative world, Jess’s insights are some of the most honest and impactful you’ll hear in 2025.

Episode 76 Chapters:

00:00 Introduction

06:02 Overcoming Public Speaking Fears

09:05 The Journey of Artistic Exploration

12:00 The Impact of Distractions on Creativity

14:59 Building a Portfolio Through Competitions

17:51 The Importance of Outreach in Creative Careers

24:00 The Role of Free Work in Career Development

29:52 The Influence of AI on Creativity

32:55 Finding Balance in Creative Pursuits

35:51 The Importance of Self-Awareness

38:54 Mastery vs. Momentum Mindset

44:37 The Future of Creativity in an AI World

01:00:25 The Power of Authenticity in Content Creation

01:05:42 The Journey of Daily Content Creation

01:12:00 Transitioning from Free Work to Paid Clients

01:17:51 Overcoming Imposter Syndrome

01:23:34 Finding Value Beyond Big Clients

01:30:20 Navigating the Creative Process

01:38:05 Leveraging AI in Creative Work

01:44:38 The Future of Creative Careers in an AI World

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