Why Great Leaders Start With Sleep, Not Strategy

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Season 3, Episode 241

Why Great Leaders Start With Sleep, Not Strategy (feat. Jessica Morris AND JONBOB Willis)

What if the biggest limiter of your leadership effectiveness isn’t skill, strategy, or experience—but exhaustion?

In this powerful and deeply human conversation, Mike Sipple Jr. is joined by Jessica Morris, executive health coach and wellness expert, and JONBOB Willis, creative entrepreneur and community builder, to unpack what holistic leadership really looks like in practice. From sleep deprivation and burnout to margin, community, and purpose-driven creativity, this episode reframes leadership through the lens of well-being.

The group explores why sleep is the cornerstone of peak performance, how leaders unknowingly model burnout for their teams, and why psychological safety begins with asking better questions—like “What’s feeling heavy right now?” instead of “How are you?”

They also dive into JONBOB’s community-driven initiatives like The Simple Portrait Project and Relentless 2800, illustrating how margin, play, and connection fuel creativity and resilience—both personally and organizationally.

This episode is a masterclass in human-centered, unconventional leadership for executives, founders, and anyone responsible for leading people.

In this episode, we cover:

- Sleep as a Leadership Skill: Why sleep is the foundation of emotional regulation, decision-making, and resilience

- Burnout Warning Signs: How stress shows up physically, emotionally, and relationally before leaders notice it

- The “At Your Best” Framework: Defining how you think, feel, and operate when you’re fully aligned

- Psychological Safety: How asking better questions transforms trust, engagement, and performance

- Margin & Creativity: Why protecting margin unlocks innovation and courage

- Community as Fuel: Lessons from The Simple Portrait Project and Relentless 2800

- Athlete Mindset for Leaders: Treating leadership like elite performance—with rest, recovery, and discipline

- Unconventional Leadership Defined: Leading holistically, human-first, and without waiting for permission

🔗 Links and Resources:

- Connect with Jessica Morris: https://www.linkedin.com/in/jessicamorrisky

Health Coach with Vytalize Health, Health Coach & Wellness Leader & Founder of RYTT Solutions

- Connect with JONBOB Willis: https://www.linkedin.com/in/jonbobdotcom

Relentless 2800: JOIN or start a team TODAY https://www.relentless2800.com

Simple Portrait Project: https://www.thesimpleportraitproject.com

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