Bad Boss Confessional 02: Broken, Better, and Whole: A Coach’s Journey to Heart-Led Leadership
Jul 30, 2025
Shasheen Shah, a coach for founders and leaders, shares his transformative journey from high-powered hustler to heart-led healer. He candidly discusses how the pursuit of success almost shattered him, prompting raw self-reflection and emotional growth. Shasheen touches on ego traps, the inner critic, and the profound loneliness often found in achievement. He emphasizes the importance of authentic self-care and shadow work, highlighting how embracing vulnerability can lead to genuine joy and connection.
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Coaching On The Move
- Shasheen prefers moving during sessions and often coaches while walking, hiking, or with his dog.
- He says physical movement helps him connect, listen, and channel ideas in session.
Tech Success That Crashed Hard
- Shasheen recounts building a dot-com at 29 that peaked at a potential $100M exit and then collapsed due to cash problems.
- The failure forced an existential reckoning about ego, significance, and unmet childhood needs.
The 30-In-30 Challenge That Launched Coaching
- Shasheen describes deciding to become a coach after a mentor challenged him to help 30 people in 30 days.
- That push led to coaching work, a Tony Robbins contract, and a slow professional arc into coaching.
