Episode 9
Why Achievement Is Quietly Costing You More Than You Think with Hayden Lee
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.…
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
Show notes
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/
About The Living Question
The Living Question is a long-form leadership and decisiom-making podcast hosted by Jason Lee for founders, CEOs, entrepreneurs, and leaders navigating high-stakes business transitions, entrepreneur burnout, and life decisions strategy alone cannot answer. Each episode slows down one real crossroads: selling a company, staying or leaving, scaling through burnout, rebuilding after success, choosing integrity over momentum, navigating a leadership transition, or redefining success when the old scoreboard stops working. With calm pressure and precise questions, Jason helps guests stop performing certainty and name the real decision, the hidden cost, and the version of themselves the choice requires. Grounded and unhurried, the show is not about doctrine, spiritual branding, or productivity hacks. Faith appears as lived discernment: the conviction you cannot un-know, alongside intuition, conscience, values, and self-trust. Together, these inner signals shape public choices in work, money, relationships, identity, purpose, and direction. If you are carrying a living question of your own, this is a place to borrow courage from people who have stood at the edge of reputation, momentum, and belonging—and still stayed with uncertainty long enough to choose a path they could actually live with.