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.

• (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

• Website: https://www.haydenlee.com/
• Hayden Lee on LinkedIn: https://www.linkedin.com/in/haydenleemcc/

When the life you built starts draining you, how do you know whether to push harder or finally let it change? Dr. Erin Burgoon joins Jason Lee to explore why slowing down can feel genuinely unsafe for founders, executives, and high achievers whose identity has been shaped by achievement. Erin shares how burnout forced her to question the coaching business she had built, what happened when she gave herself a time bound experiment in rest, and why the greatest cost was not lost income but the loss of a familiar professional identity. Together, Erin and Jason discuss nervous system regulation, Internal Family Systems, the difference between excitement and durable joy, and the courage required to stop performing certainty long enough to hear what is true. This conversation offers a grounded way to recognize when grit has become avoidance, redefine what it means to provide, and make choices rooted in joy, self trust, and a deeper sense of purpose.

• (00:00:00) Why slowing down can feel permanent
• (00:05:38) How to tell discipline from avoidance
• (00:11:06) The nervous system fear beneath constant action
• (00:16:24) Creating a time bound experiment with rest
• (00:22:32) The identity cost of stepping away from work
• (00:29:06) Redefining provision, care, and a meaningful day
• (00:35:42) Treating the body with love instead of criticism
• (00:42:36) Why joy begins with nervous system safety
• (00:49:18) Joy as a spiritual center and source of clarity
• (00:56:12) Small practices that make joy more accessible

• Website: https://drerinb.com/
• LinkedIn: https://www.linkedin.com/in/drerinb/

Jason Lee sits down with Chris Gray — marketer, co-founder of Red Palm, and Front Row Dad — to unpack the decision logic couldn't make, and the alignment work that made his gut trustworthy in the first place. Chris shares how he moves from head to body before reacting, why joy is the most vulnerable emotion, how he built AI "spiritual guides" shaped by the Bhagavad Gita, the Bible, Eckhart Tolle, and Richard Rohr — and the moment one of those agents showed him that turning surrender into a framework was just his ego grabbing the wheel. They dig into faith moves versus good moves, why the peace that goes beyond understanding requires forfeiting your right to understand, why clients are ultimately buying confidence, and how the state you decide in determines the quality of the action. Chris closes with his current living question: what does it actually look like to feel your feelings, when you've spent a lifetime equating feeling with weakness?

• (00:00:00) - Welcome to The Living Question
• (00:00:47) - The decision logic couldn't make
• (00:07:00) - Keeping someone the numbers said to cut
• (00:08:10) - Why joy is the most vulnerable emotion
• (00:12:30) - Catching unconscious reactions at home
• (00:17:45) - AI as a spiritual guide
• (00:20:17) - When surrender becomes another framework
• (00:26:50) - Selling confidence while Google rewrites the rules
• (00:33:27) - How leading from the head once protected him
• (00:38:33) - Chris's living question: learning to feel

• Connect with Chris Gray @yochrisgray — Instagram, Facebook, LinkedIn
• Red Palm, Chris's marketing company for home service businesses: https://redpalm.us
• The Surrender Experiment by Michael Singer: https://www.amazon.com/Surrender-Experiment-Journey-Lifes-Perfection/dp/080414110X
• Front Row Dads: https://frontrowdads.com