In this deeply vulnerable and relatable episode of High, Low, and Unexpected, Shaun Gordon sits down with Kelley Gilster—wedding filmmaker, serial entrepreneur, and co-founder of The Level Up Co.—to talk about the emotional cost of success, rediscovering purpose after burnout, and building a business that supports your real life, not just your goals.

Together, they unpack Kelley’s journey through motherhood, running four businesses, hitting her financial peak in 2024 while feeling at her lowest emotionally, and the wake-up call that brought her back to herself. Shaun also reflects on his own recent retreat experience and shares how emotions, the Enneagram, and a deeper awareness are shifting the way he shows up as a leader.

Key Topics Covered:

• The myth of “having it all together” and what happens when you don’t
• Kelley’s unexpected path into motherhood and entrepreneurship
• The emotional weight of 2024—and why success felt empty
• Building Level Up Co. and the power of aligned partnerships
• Enneagram Type 3w2 and how it shaped Kelley’s mindset
• The power of awareness, therapy, and showing up as your whole self

This is a must-listen for anyone juggling ambition and real life, and anyone who’s ever felt like their achievements weren’t enough. You’ll walk away challenged, inspired, and seen.