Hayden Lee lives by one question: at the end of my life, will I regret not trying this? In this conversation, Jason sits down with his first ever coach, an executive and leadership coach who has worked with leaders at companies like Google and Meta and has been named a top 20 LA coach eight times. Hayden explains why the most useful definition of faith for him is unshakable self belief, how years of rejection as a professional actor trained him to collect nos without flinching, and why he treats self belief as a skill you practice rather than a trait you are born with. He walks through the origin of his annual coaching retreat in France, the real cost of chasing it (time, not money), and the two filters he runs every big idea through: the no regrets test and a head, heart, and gut check that keeps a bias for action from turning into blind ambition. The conversation then slows down into presence, why Hayden resists the word surrender in favor of letting go, and what a quiet Saturday spent vacuuming dog hair out of his car taught him about rushing. Along the way, Jason and Hayden get honest about what deeper work actually costs: fewer external scoreboards, saying no to transactional clients, and a shorter list of people who want to have a real conversation. If you are a founder or leader weighing a decision that strategy alone cannot answer, this episode is a grounded look at how to choose a path you can actually live with.
Chapters:- (00:00:00) Will I regret not trying? Meet leadership coach Hayden Lee
- (00:06:35) Faith as unshakable self belief and the professional rejectee
- (00:12:48) Enneagram 3s, the achievement drive, and doing the reps
- (00:19:36) Same purpose, different medium, and the real cost of the France retreat
- (00:25:48) The no regrets value, the full body hell yes, and the head, heart, gut filter
- (00:32:40) Thinking, feeling, and action: knowing how you are wired
- (00:39:35) Surrender vs letting go, and the car vacuuming moment
- (00:46:30) Nervous systems on overdrive: slow is smooth, smooth is fast
- (00:53:25) Redefining success: external wins and internal fulfillment
- (01:00:15) Saying no to transactional work, and trusting another wave will come
Links and Resources:- Website: https://www.haydenlee.com/
- Hayden Lee on LinkedIn: https://www.linkedin.com/in/haydenleemcc/