#67 Matthew Pridgen: When Cognitive Dissonance Breaks Open

"You can only live with so much cognitive dissonance in your life." - Matthew Pridgen

Matthew Pridgen joins Ken Woodward for a raw, wide-ranging conversation about how questions can crack open denial and move us toward truth, repentance, and reconciliation.

Matthew shares his dramatic journey from addiction and a near-fatal suicide attempt to a decades-long pursuit of faith, justice, and historical honesty. His pivotal moment was when an eight-year-old girl asked, “Why did you take my church down?” after a tent revival in Charleston’s historically Black East Side, which became the question that launched his racial awakening.

Together, they explore how American “mythology” hides the realities of slavery, Jim Crow, and modern dog whistles, and how the Black church has sustained a prophetic witness against oppression.

The episode highlights the personal cost of cognitive dissonance, the freedom of living without lies, and a central challenge for today: are Christians willing to abandon Christian nationalism and follow Jesus’ actual teachings?

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

Be sure to subscribe to the weekly Curated Questions Dispatch newsletter for more fun with questions and curiosity! (https://substack.com/@curatedquestions)

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#65 Mitchell Osmond: Everything Is Hard - Choose Your Hard

"Literally everything in life is hard. The question is, what cost are you willing to pay? And you pay that willingly and happily because you value it." - Mitchell Osmond

In this episode of Curated Questions, Ken Woodward sits down with Mitchell Osmond, founder of Dad Nation Co., and host of the Dad Nation Podcast (Top 5% globally), to explore a hard but liberating truth: everything in life is difficult; the question is which difficulty we choose.

Mitchell shares the moment a single question at a funeral, “Are you living a life worthy of imitation?” forced him to confront his health, marriage, finances, and legacy. From that reckoning emerged a framework for growth rooted in discomfort, integrity, and honest self-inquiry.

Together, Ken and Mitchell examine why confidence is built through keeping promises, how avoiding hard questions quietly shapes our futures, and why legacy is forged at home as much as at work.

The conversation challenges the myth of ease, reframes struggle as a signal of alignment, and invites listeners to define success on their own terms. Ultimately, this episode is a call to stop outsourcing meaning, and to choose the hard that leads to a life worth living.

Mitchell is launching a new group coaching program, the High Performance Husband Accelerator! All the details can be found at https://www.dadnationco.com/accelerator

Mitchell is offering The Connection Code as a gift. 50 questions to spark the fun and get the fire back is available at https://www.dadnationco.com/code

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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#64 Ken Woodward: What Questions Are You Carrying Forward? Reflections on 2025

"What are the questions you will be carrying into the year, such that it will be a celebration of your becoming?" - Ken Woodward

This year-end Curated Questions episode is a reflective curation of the questions that shaped several conversations throughout 2025. Rather than offering a rapid recap of every episode, Ken highlights a handful of moments that reveal how intentional questioning can clarify purpose, interrupt unhelpful patterns, and guide meaningful becoming.

Across stories from entrepreneurs, scientists, artists, and personal reflection, the episode explores questions that ask us to define the change we seek to make, consider who we are becoming, and choose where to place our attention. Along the way, listeners are reminded that good questions often emerge only after many imperfect ones, that perspective shapes dignity and connection, and that small mental reframes can act as powerful resets.

As the year closes, the episode becomes an invitation: to name the questions that mattered most in 2025, to carry one forward with intention into 2026, and to trust that a better world is built by those willing to keep questioning.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

Ensure to subscribe to the Curated Questions Dispatch weekly newsletter on Substack.

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#62 Haru Yamada: Flashlights, Lanterns, and the Way We Listen

"Not being a hundred percent sure all the time is a weird strength." - Haru Yamada

In this episode of Curated Questions, Ken Woodward is in conversation with Dr. Haru Yamada, a sociolinguist, intercultural communication scholar, and author of Kiku: The Japanese Art of Good Listening, to explore what it really means to listen. Haru traces her early understanding of questions back to age four, when she moved from Tokyo to New York and had to use questions as a tool for language, belonging, and survival.

Together, they unpack how culture shapes communication: English often rewards “flashlight” questioning, the precise, content-driven clarity, while Japanese culture tends to favor a “lantern” approach that illuminates context, relationship, and what isn’t said. Haru also shares the harrowing accident that reshaped her understanding of listening as a health practice, linking felt-heard experiences to relational, mental, and even physical well-being.

In a noisy, multitasking world, this conversation reframes listening as an active, life-giving skill, and a compass for navigating each other with empathy.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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#60 Radhika Dutt: From Goals to Puzzles: How Questions Outperform OKRs in Real Teams!

"We vote with our labor for the world we want to create. If you don't reflect on what you're doing, how do you know you're casting the right vote?" - Radhika Dutt

In this episode of Curated Questions, host Ken Woodward engages entrepreneur and author Radhika Dutt in a profound exploration of how questions can transform organizations from goal-driven to puzzle-solving entities. Radhika is the author of "Radical Product Thinking" and shares her journey from MIT to becoming a serial entrepreneur to developing the puzzle-based leadership OHLA framework (Objectives, Hypotheses, Learnings, Adaptations).

The conversation reveals how traditional goal-setting, rooted in 1940s assembly-line thinking, fails in today's complex environment, where creative problem-solving matters more than repetitive execution.

Radhika demonstrates through a live experiment how "puzzles" energize while "goals" burden, explaining that puzzles tap into internal motivation rather than external pressure. She emphasizes the critical importance of reflection, a practice she credits with enabling better decision-making both personally and professionally.

Drawing from her nine languages and global experience, including living in post-apartheid South Africa, Radhika offers insights on creating psychological safety for questions across cultures. The episode culminates with practical guidance on implementing puzzle-based thinking in organizations, showing how asking better questions leads to ownership, engagement, and transformative results.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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#59 Ken Woodward: The Insight Pause: When a Single Truth Rewrites Your Story!

"The Insight Pause is sitting in the rubble of your shattered worldview before clearing a single stone." - Ken Woodward

In this solo episode, Ken Woodward introduces The Insight Pause—a five-step framework for navigating the moments that crack open our worldview. Through his own story of confronting the hidden history behind the Indigenous names and artifacts that shaped his childhood landscape, Ken explores how insights arrive fully formed, unsettle our identities, and demand more than quick fixes or defensive reactions.

He walks listeners through the foundational skills that prepare us for these moments, the instant of recognition, the sacred pause that follows, and the slow work of integrating unsettling truths into a new, liberated worldview.

Whether you're rethinking long-held beliefs, noticing contradictions you can’t ignore, or sensing that something in your life no longer fits, this episode offers a practical and compassionate guide for holding discomfort without collapsing into denial or overreaction.

Discover how the Insight Pause can transform the questions you carry—and the person you’re becoming.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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#57 Jaimie Reese: Building Enduring Trust Through the Questions We Ask!

"When you have a trusting environment, it is exactly to hold each other accountable." - Jaimie Reese

What does it take to build trust in one of the world’s largest bureaucracies? Former U.S. Navy Senior Executive (SES) Jaimie Reese joins Ken Woodward to explore how genuine curiosity and courageous questioning can reshape systems, teams, and lives. From the aftermath of 9/11 to boardrooms and the Pentagon, Reese shares hard-won lessons on leadership, timing, and the art of listening when stakes are high.

Through stories that move from crisis to calm, she unpacks why trust isn’t granted by authority but earned through everyday inquiry—how slowing down, asking better questions, and truly hearing the answers can transform any organization. Jaimie traces the invisible threads between humility, communication, and change, revealing what happens when leaders replace certainty with curiosity.

This episode challenges every listener to reimagine leadership as an ongoing dialogue. Because, as Jaimie reminds us, “Leadership is a conversation you have with the future—one question at a time.”

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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#56 Garrett Wood: Safety, Burnout, and the High-Achievement Mask!

"The closer you become with these people while you're wearing that mask, the more distant you actually feel from the people around you." - Garrett Wood

In this episode of Curated Questions, host Ken Woodward engages in a deep conversation with Garrett Wood, a national board-certified health and wellness coach and certified clinical hypnotherapist. Garrett shares his insights on the hidden tolls of high achievement, addressing issues such as perfectionism, imposter syndrome, and burnout. He explores the power of questions and how they can transform our understanding of identity, worth, and achievement.

The discussion dives into the paradox of wearing masks to gain social acceptance, the first signs of burnout manifesting as cynicism, and the importance of creating authentic connections. Garrett also discusses practical strategies, such as non-sleep deep rest, to enhance performance and creativity, as well as the role of self-compassion in maintaining mental health.

This episode offers valuable perspectives on how to navigate and make sense of the world through the power of questioning.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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#55 Ken Woodward: The Locked Door: How Avoided Questions Hold the Key to Transformation!

"Your avoided question isn't just personal development, it's an act of resistance." - Ken Woodward

In this episode of Curated Questions, host Ken Woodward explores the transformative power of confronting the questions we're avoiding. Delving into neuroscience, psychology, and personal reflection, he highlights why these avoided questions create discomfort and how they serve as a gateway to significant change.

Ken introduces tools and methodologies to help listeners identify and tackle these questions, both in their personal lives and within organizations. With practical advice and real-world examples, this episode encourages listeners to pause, reflect, and take actionable steps towards growth.

Ken also underscores the importance of curiosity and its role in overcoming avoidance, ultimately leading to meaningful transformation.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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#51 Dave McGurk: Mental Models, Cognitive Frameworks, and the Questions That Disrupt Them!

"If we start talking about developing people, you have to ask those deep questions." - Dave McGurk

Dave is a transformational leader who bridges military precision with cutting-edge organizational development. As Founder and CEO of Veridian Perspective and Vice President at Apogee Global RMS, Dave brings over 20 years of executive leadership experience. His impressive 30-year military career includes Training Operations Director at the U.S. Army Command and General Staff College, Army Enterprise liaison and senior executive advisor to U.S. Army European, African and Special Operations Command teams.

He has managed multi-billion-dollar budgets, led teams of hundreds, and influenced policy at the highest levels of government—including presidential-level decisions. His approach blends 30 years of military leadership, adult education, & neuroscience to create AI-powered diagnostics, hyper-personalized development, and dynamic simulations for resilient leaders in a volatile world.

Ken Woodward engages in a profound discussion with Dave McGurk, a transformational leader with a rich background in military leadership and organizational development. Dave shares his experiences, including a pivotal moment during his deployment in Iraq where he learned the cultural importance of time through the simple act of removing his watch. This revelation led him to question the embedded cognitive frameworks that shape our understanding of the world.

Through deeply reflective questions, Dave emphasizes the importance of framing problems accurately, understanding inherited mental models, and fostering genuine connections with others. He introduces his innovative seat swap counseling method, which promotes genuine feedback and psychological safety. This episode dives into the power of questions in personal growth and leadership development, urging listeners to challenge their assumptions and continuously evolve.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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#50 Mike Hilson: Why "Who Do I Say I Am?" Changes Everything!

"Who am I? Was never gonna turn out well. Who do I say I am? Had a chance." - Mike Hilson

Mike Hilson is the Senior Pastor of New Life Church based in La Plata, Maryland. Since 1999, the church has grown under his leadership from a congregation of less than 100 into several churches and video venues. The New Life Network of churches now averages more than 5,000 in regular attendance across Maryland, Northern Virginia, and online.

Mike currently serves on the Board of Trustees at Southern Wesleyan University. He is also a member of the Chesapeake District Board of Administration for the Wesleyan Church. He lives in the D.C. Metro Area with his wife, Tina and their three adult sons.

Mike has written several books, including Napkin Theology, Speak Life, A Significant Impact for Christ, Heart of a Leader: Moses, and a series of books called Coffee with the Pastor.

These successes led to numerous invitations to teach and coach leaders from multiple regions, states, denominations, and nations.

In this episode, host Ken Woodward welcomes Pastor Mike Hilson, senior pastor of New Life Church. They delve deep into how questions shape identity, leadership, and personal growth.

Mike shares his journey, from wrestling with self-identity as a child to leading a thriving network of churches. Key discussions include the necessity of creative boredom, the evolution of the question 'Who do I say I am?', the importance of strategic delegation, and balancing doctrinal adherence with familial love.

The episode addresses how asking the right questions can uncover more profound truths, facilitate effective leadership, and nurture valuable relationships.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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#49 Naomi Campbell: The Key to Helping Others Find Their Own Questions!

"Questions are an extremely sophisticated thinking skill that everyone can use and practice all the time." - Naomi Campbell

In this episode, host Ken Woodward is in conversation with Naomi Campbell, Director of the Right Question Institute (RQI) Legal Empowerment Program. They delve into the transformative power of teaching people to ask questions, highlighting its impact across various fields, including education, legal practice, and healthcare.

Naomi shares her journey from an inquisitive childhood encouraged by her family and school, through law school at Harvard, to her work in Mexico City advocating for migrant workers. The episode emphasizes the importance of questioning as a sophisticated skill that fosters personal agency and enhances democratic participation. Naomi also discusses RQI's unique methods for teaching this skill and how they support change agents in different communities.

The conversation provides insightful examples of how empowering people to formulate their own questions can lead to meaningful social change and better navigating decision-making systems.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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#48 Ken Woodward The Curated Questions Origin Story: When It All Began!

" Once you have the question, the hard part begins." - Ken Woodward

In this solo episode, host Ken Woodward delves into the origin and development of the 'Curated Questions' project, which began in 2018. Ken shares his personal journey of curiosity, inspiration from Tim Ferriss' podcast, and the influences that led to the creation of his blog and subsequent podcast.

Highlighting notable milestones and influential interviews, Ken discusses the structure and purpose of the Curated Questions website and its various elements, including famous questions and lists. He also reflects on the profound impact of asking meaningful questions, illustrated with personal anecdotes.

The episode encourages listeners to embrace curiosity and engage with the world through the power of well-chosen questions.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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#47 Maury Rogow: How Questions Create Instant Trust in Any Conversation!

"You were the most interested person in the room, and you're gonna get love." - Maury Rogow

Maury Rogow is all about storytelling. He is the CEO of the Rip Media Group and creator of the Story2Sales methodology that's generated over $150 million in trackable revenue for clients. I appreciate the tag line, "Your brand will thrive or die, based on the story you tell."

Maury's unique journey spans high-tech success and Hollywood storytelling. He built his business career at companies like Avaya, Lucent Technologies, and GeoTel—a startup that sold to Cisco Systems for over $1 billion. He then pivoted to Hollywood, serving as executive producer for feature films like "Bedrooms" and "Enter The Dangerous Mind," and working with industry legends including the creator of the Batman franchise.

Today, Maury combines business acumen with cinematic storytelling to help Fortune 1000 companies like Comcast, Kaiser Permanente, and Ben & Jerry's create compelling brand narratives. His approach recognizes that in our noise-filled marketplace, every company must master storytelling to survive and thrive.

Maury has proven that great stories don't just entertain—they sell. He's written several books, with his latest on the horizon being "Your Story Can Be Your Superpower - Selling in an AI world." He has been featured in Forbes, Inc., and Entrepreneur magazines.

In this episode of Curated Questions, host Ken Woodward engages with Maury Rogow, CEO of RipMedia Group, to explore the transformative power of questions in both personal and professional contexts. Maury shares pivotal moments in his career, from telecommunications to Hollywood, emphasizing how a single question can change a transactional relationship into a meaningful connection.

The discussion covers the importance of storytelling, the benefits of embracing unique traits, the impact of framing on emotional responses, and effective strategies for leveraging questions in sales and daily life. Maury also offers practical advice on finding balance in business, the role of AI in asking the right questions, and shares key resources and techniques for developing better questioning skills. Listeners are encouraged to take on an audience challenge to spend a day asking only questions and to reflect on the impact it has on their interactions.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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#46 Dr. Matt Lampe: Why the Right Question Feels Like an Invitation

"The meaning of your communication is the result you are getting." - Dr. Matt Lampe

With a Doctorate from Alliant International University's California School of Professional Psychology, Matt has dedicated his career to transforming how organizations approach change, leadership development, and workplace agility.

He is currently leading enterprise-wide organizational change efforts as part of Business Oregon's flagship modernization initiative, which focuses on aligning internal systems, strengthening operational infrastructure, and enhancing statewide service delivery to help businesses throughout Oregon.

Sponsored by the non-profit Science For Work, Matt hosts the "Science for Work Podcast," where he explores the science behind creating healthier, more effective work environments through conversations that translate heady scientific research findings into practical action steps.

His consulting practice helps organizations navigate complex transformations through change management, leadership development, strategic planning, and project management—combining data-driven insights with compelling storytelling.

Matt's philosophy centers on creating cultures where people can thrive. He's learned that data alone isn't enough to drive change; it's the combination of solid research with relatable storytelling that truly motivates action and engagement. And if that wasn't enough, he is also a contributing writer to PositivePsychology.com.

In this podcast episode, host Ken Woodward delves into the significance of questions in both professional and personal spheres with Dr. Matthew R. Lampe, an expert in organizational change and leadership development. Highlighting the vital role questions play in verifying communication, navigating change, and building trust, Matt shares insights from his experience in managing organizational transformations and personal growth. The conversation also touches on the deep tradition of yearly trips to Yosemite, offering a unique perspective on how consistent reflection against an unchanging backdrop can facilitate personal growth and evolution. Additional elements include updates about the curated questions community, announcements of new features, and an introduction to the Science for Work Podcast.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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#44 AI Alan Turing: What Machines Can’t Imitate - On Questions, Doubt, and the Discipline of Curiosity

"I suspect beauty comes when a question both sharpens and enlarges your vision." - AI Alan Turing

In this special episode, we step back to a cold December night in 1951 and into the warm, wood-paneled room of The Britons Protection, a historic Manchester pub. Across the table sits Alan Turing, the mathematician, wartime codebreaker, and one of the founding figures of computer science, who is brought to life through an AI simulation.

Best known for his role at Bletchley Park during World War II, Turing devised techniques and machines, including the Bombe, that cracked the German Enigma code and helped shorten the war by years. His groundbreaking 1936 paper on “computable numbers” introduced the concept of the universal machine, and became the theoretical foundation for modern computers. Later, at the University of Manchester, he advanced early computing, explored artificial intelligence, and even pioneered mathematical biology.

Our imagined conversation, grounded in historical detail and Turing’s own writings, delves into his enduring fascination with questions: how to ask them, when to abandon them, and why some are worth carrying for a lifetime. We discuss the interplay between beauty and inquiry, the discipline required to avoid seductive but unproductive lines of thought, and the place of doubt as an essential human strength.

We also revisit his famous “imitation game” — now known as the Turing Test — and consider the boundaries of machine intelligence, the dangers of mistaking simulation for genuine dialogue, and the questions that only humans can keep alive, all while wrestling with the meta question, "Is this machine thinking?"

This episode blends history, philosophy, and imagination while inviting you to consider what it means to think, to doubt, and to remain fully human in an age of advancing machines.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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#42 Ashley Kirsner: Want Connection? Skip The Small Talk

"It is much safer to be vulnerable than you might think." - Ashley Kirsner

Ashley is the founder and director of Skip the Small Talk, and believes in the efficacy of high-quality person-to-person interaction for improving psychological health. She has conducted research with professors at prestigious organizations such as Cornell University, the Harvard Decision Science Lab, and the Harvard Business School, on social and clinical psychology topics ranging from decision-making and implicit biases to facial expressions in borderline personality disorder patients.

Ashley gained hands-on therapeutic experience as a suicide hotline phone responder and as a peer counselor at Cornell. Ashley received her B.A. in Psychology from Cornell University and turned down acceptances to doctorate programs in order to devote her time to Skip the Small Talk. She received a fellowship from the Harvard Divinity School for individuals who have demonstrated a social impact in the domain of creating meaningful communities. Skip The Small Talk events are regularly held internationally, as well as an online options.

In this engaging episode of 'Curated Questions,' host Ken Woodward sits down with Ashley Kirsner, the founder and director of 'Skip the Small Talk.' They explore the transformative power of meaningful conversations, the science behind vulnerability, and the surprising benefits of structured social interactions.

Ashley shares her experiences from the suicide hotline, her inspiration for starting 'Skip the Small Talk,' and how intentional question design can foster deeper human connections. The conversation also delves into the physiological benefits of social interactions, ethical considerations in community building, and the importance of creating safe spaces for vulnerability. Tune in to learn how these insights can help you build stronger, more authentic relationships in your own life.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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#41 Robert Sturman: The Question of Beauty: A Photographer's Pursuit

"I realized that paying attention is a form of a question." - Robert Sturman

Robert Sturman is a seeker and visual storyteller. Driven by an unshakeable belief that beauty exists everywhere. He has pursued this vision as an Official Artist of the Grammy Awards and the FIFA World Cup, and as a globally recognized photographer who captures the healing power of humanity through yoga. After studying art at UC Santa Cruz and Memphis College of Art, he discovered that his life itself, was art, and needed to become a masterpiece.

Robert has mastered finding profound beauty in unexpected places - from the streets of Manhattan to San Quentin Prison, from Kenyan orphans to breast cancer survivors bearing their scars. His philosophy is rooted in Rumi's words: "I can't stop pointing to the beauty."

Through his lens, Robert demonstrates that everyone belongs and vulnerability becomes strength. His approach reveals that the most potent questions aren't about technique, but about trust, connection, and helping people recognize their own light. He seeks beauty where others see difficulty because he understands transformation happens when we're willing to look deeper.

The most heartfelt title he answers to is Dad to Otis the Handsome Hound, an 85-pound English American Redtick Coonhound who was rescued following animal testing. Otis has nearly 7K Instagram followers and is an advocate for cruelty-free testing.

In this episode of Curated Questions, host Ken Woodward converses with renowned visual storyteller Robert Sturman. Robert, celebrated for his profound and inclusive photography, shares insights on capturing the healing power of humanity through his lens. The discussion explores Robert's journey from photographing idyllic beach yogis to documenting yoga practice in diverse and challenging settings, including maximum security prisons and amongst war veterans. Through his lens, he celebrates vulnerability, trust, and beauty in unexpected places. Robert also delves into his advocacy work with his rescued animal companion Otis, highlighting the critical issue of cruelty-free product testing. Throughout the episode, recurring themes focus on the transformative power of paying attention, the courageous response to criticism, and the continuous pursuit of personal and artistic growth.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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#30 Tim Molnar: Intentionally Cracking Love's Enigma Through Analytics

Host Ken Woodward talks with Tim Molnar, who shares how he developed his strategic dating framework by applying research principles to dating, emphasizing the importance of asking better questions about ourselves and potential partners. He explores how traditional metrics like "feeling a spark" can be misleading compared to questions about safety, visibility, and energy levels after being with someone. The conversation highlights how self-awareness, intentional action, and thoughtful questioning can increase the probability of building fulfilling relationships while also creating space for continued growth and evolution within partnerships.

#28 Lisa Wimberger: From Lightning's Wrath to Neuro Resilience

Host Ken Woodward converses with Lisa Wimberger about the transformative power of curiosity and the practice of Neurosculpting. Lisa shares her harrowing experiences of being hit by lightning and suffering from non-epileptic seizures, which led her to develop a unique healing modality by combining brain science and mindfulness. Through this dialogue, Lisa explains how asking the right questions can lead to profound personal growth and healing, providing practical insights into emotional regulation and neuroplasticity. Listeners also gain a deeper understanding of how Lisa has utilized her experiences to help corporate leaders, law enforcement, and first responders improve their mental resilience.