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In this raw and powerful episode of You Winning Life, Jason Wasser welcomes Adrian Koehler, a high-impact executive coach and leadership trainer, to discuss the transformative power of commitment, language, and self-awareness in both life and leadership.

They explore how getting “stuck” in career or personal relationships often stems from a lack of clarity, aligned values, or the fear of fully committing. Adrian breaks down the difference between trying and committing, shares insights from coaching founders and prison inmates alike, and opens up about his own growth through fatherhood, failure, and radical honesty.

The episode covers everything from reinventing your job description to challenging toxic workplace dynamics, and how proactive conversations and deep accountability can help you play to win—not just survive.

Key Topics Covered:

🔹 Commitment vs. Trying – why "trying" keeps you stuck
🔹 The power of language in leadership and personal transformation
🔹 Coaching vs. traditional therapy – how results and accountability shift outcomes
🔹 How to rewrite your job description and align with your purpose
🔹 The role of self-awareness in authentic relationships
🔹 Rewiring chronic complaints (“rackets”) in personal and professional life
🔹 Using personal stories and feedback loops to drive growth
🔹 Building strong family standards and leadership at home
🔹 The difference between playing to win vs. playing not to lose

Memorable Moments:

🎧 Adrian shares how Paul Simon’s “Still Crazy After All These Years” helped him through tough times
🛠️ Real-world advice on how leaders can use audacity and alignment to thrive
📢 Why TEDx talks and unedited conversations matter more than polished content

Resources & Links:

🌐 Learn more about Adrian Koehler: https://www.takenewground.com

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In this episode, Jason is joined by award-winning speaker, educator, and author, Scott Fried who has been a significant presence in Jason's life since 1994/95, when Jason first heard him speak at his childhood synagogue in South Florida. That initial encounter sparked a lasting connection. Their bond has remained strong for over 30 years, with Scott's work and personal story continuing to inspire Jason.

Scott shares his transformative personal journey and insights on living with purpose, self-love, and self-responsibility. He reflects on his life with HIV and his mission to help teens and adults make better life choices, focusing on self-empowerment and compassion. The conversation explores the concept of elegance—not just as a physical attribute, but as a way to live with grace, integrity, and a deep sense of personal growth. Scott also touches on the importance of vulnerability, compassion, and emotional intelligence in building meaningful relationships and embracing life's challenges.

Key Takeaways:

• Personal Growth and Elegance: Elegance is more than just appearance—it’s about living with grace, emotional balance, and self-awareness, especially in times of hardship.
• Self-Love and Responsibility: Scott shares how his own experiences shaped his understanding of self-love and the importance of self-care in supporting others.
• Compassion and Vulnerability: Acknowledging and embracing vulnerability is essential for personal growth and building strong, compassionate relationships.
• Purpose and Agency: Taking responsibility for our lives and understanding the balance between joy and struggle helps us stay aligned with our higher purpose.

In This Episode You’ll Hear About:

• Scott’s personal journey with HIV and how it has influenced his perspective on life, love, and self-empowerment.
• The concept of "elegance" in personal growth and how it applies to self-care, leadership, and interactions with others.
• Insights into self-acceptance and why it's crucial for living a fulfilling life.
• Stories of vulnerability, tenderness, and resilience, and how these qualities shape our journeys as adults.
• The importance of surrounding ourselves with compassionate, accepting relationships and fostering radical self-acceptance.

Featured Books:

• If I Grow Up: Talking with Teens about AIDS, Love, and Staying Alive
• My Invisible Kingdom: Letters from the Secret Lives of Teens
• A Private Midnight: A Teenager’s Scrapbook of Secrets
• How to Raise an Elegant Teen: The ABCs of Gen Z Parenting

Resources:

• Scott Fried’s website: Scott Fried
• Pandemic Playbook course at Colby College: AIDS and the Meaning of Life

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In this episode of You Winning Life, Michael Reddington, a Certified Forensic Interviewer and expert in strategic communication, joins Jason to break down the power of listening, asking better questions, and handling high-stakes conversations. Michael shares investigation-based techniques that can transform the way we communicate in business, relationships, and personal growth.

Together, they explore effective communication strategies, career paths and problem-solving techniques, and how situational awareness and emotional intelligence shape impactful conversations. Jason also shares how helping a violin teacher expand his brand reinforced the importance of asking for what you want—a principle Michael applies to business, leadership, and everyday interactions.

If you’ve ever struggled with feeling undervalued, handling difficult conversations, or understanding different perspectives, this episode is for you.

What You’ll Learn in This Episode:

✔️ How forensic interrogation techniques apply to business, leadership, and personal relationships
✔️ The importance of context and empathy in conversations
✔️ How to ask better questions to uncover key insights and build trust
✔️ Strategies for handling difficult conversations and managing emotions
✔️ Why taking action creates clarity when dealing with workplace ambiguity
✔️ How to reframe questions to guide people toward better outcomes
✔️ The role of situational awareness in effective communication
✔️ Understanding hyper-rational individuals and how to engage with them emotionally
✔️ Avoiding misunderstandings by asking open-ended questions rather than leading ones
✔️ The impact of self-awareness and emotional intelligence in business and relationships

Key Takeaways from The Disciplined Listening Method:

🔹 Illustrate before investigating to create a comfortable environment for sharing information
🔹 Focus on the outcome, not immediate emotional reactions
🔹 Reframe questions positively—ask what someone wants rather than what they want to avoid
🔹 Use non-accusatory language—shift from “Did you?” to open-ended phrasing
🔹 Say, "Please correct me where I'm wrong" to encourage more open communication
🔹 Recognize that action creates clarity in ambiguous situations
🔹 Let people “gas themselves out” before responding in high-emotion conversations


Buy his book: The Disciplined Listening Method: How A Certified Forensic Interviewer Unlocks Hidden Value in Every Conversation

🌐 Website: michaelreddington.com

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