118: Your Questions Answered: Leadership, Mindset & Decision-Making

In this special Q&A leadership session, Dwayne Kerrigan brings forward one of his most personal and powerful teachings yet—an unfiltered look at problem-solving, decision-making, emotional mastery, strategic planning, and the rituals that shape high-performance leaders.

Responding to 51 listener questions, Dwayne breaks down the “three pillars of progress,” the psychological layers of every problem, why decision-making is a muscle, and how fear, uncertainty, and overwhelm quietly sabotage performance.

He shares the exact rituals he has used for decades—from weekly solitude planning to identity-based scheduling—and the transformative practice he credits with changing his life: think time.

This episode is a masterclass in intentional living and high-performance leadership, blending mindset, structure, neuroscience, and real-world business wisdom. If you’re navigating fast-moving environments, leading teams, or trying to build a more purposeful life, this conversation gives you a proven roadmap forward.

Key Takeaways:

• Decision-making is a muscle—if you don’t practice small decisions with process and ritual, big decisions will always overwhelm you.
• Your focus determines your emotional life—the meaning you attach to events shapes long-term joy or suffering.
• Rituals create identity and outcomes—weekly solitude planning, think time, and identity-based scheduling produce clarity and momentum.
• Strategic thinking requires cadence—yearly visioning, quarterly reviews, weekly planning, and daily recalibration.
• AI will disrupt faster than expected—leaders must systemize processes now to survive the shift.
• Self-love, vulnerability, and forgiveness are essential ingredients for emotional mastery and better decision-making.

Quotes:

“Decision making is a muscle .. and it's a skill set. And often times where we struggle is this area of making the tough and difficult decisions.”

“What you ritualized in practice in private is rewarded in public.”

“The business side of things should be a game. I mean, it should be fun most of the time.”

"What is going to make you a happier and more joyful person, is attaching a different meaning to the events that happen in your life.”

Resources Mentioned:

Tony Robbins – “Three Pillars of Progress,” Date With Destiny program, life-planning philosophy

Stephen Covey – prioritization framework (A/B/C method)

Waking Up App (Sam Harris) – meditation and mindfulness

ChatGPT (Teams) – referenced as part of Dwayne’s business infrastructure

SOPs (Standard Operating Procedures) – foundational to AI-based workflow agents

Identity-based scheduling – Dwayne’s personal system (Chairman, Husband, Father, Student, etc.)

Audio Timestamps:

00:00 – How meaning, not outcomes, determines happiness and fulfillment.

01:00 – Welcome, context for the live Q&A format, and session overview.

02:00 – Framing the biggest listener questions around decisions, problems, and leadership.

03:00 – The three pillars of progress and why focusing on problems makes them grow.

05:00 – The three levels of a problem: external, internal, and psychological.

07:00 – Why fear, uncertainty, and overwhelm stop people from making decisions.

09:00 – Decision-making as a muscle and the importance of rituals for small decisions.

12:00 – Managing overwhelm through physiology, breathing, and better questions.

16:00 – Focus, meaning, and how emotional patterns shape leadership behavior.

23:00 – Strategic thinking rituals: yearly visioning, quarterly...