Ask For An Answer

What happens when life flips the script and forces you to step up as the parent to your own parents?

Vivian Olodun joins Ask for an Answer for a conversation about high emotional intelligence, financial literacy, and the messy reality of navigating the sandwich generation. A best-selling author, CEO of Flourish Media, marketing strategist, and creator of Proximity to Money, Vivian built a life around building strong relationships and applying hard-won wisdom. From growing up as a military child across nine schools to launching her Substack, Vivian has dedicated her work to teaching others that proximity changes what is possible. In this episode, she and Jim dig into the emotional toll and financial maze of caring for aging parents with cognitive decline.

Can Financial Literacy Save You in a Family Crisis?

The conversation shifts to the stark realities of elderly care and why financial preparedness is non-negotiable. Vivian and Jim shed light on the unexpected gaps in traditional health insurance, the immense cost of memory care, and how proximity to money creates real solutions when high-stakes decisions arise. Vivian emphasizes the value of veteran resources, while Jim reflects on the foresight of long-term care insurance. The episode concludes with practical wisdom on emotional resilience, accepting help without judgment, and leading through life's hardest transitions with empathy and grace.

KEY TAKEAWAYS

1. How growing up in dynamic environments like military life can build exceptional emotional intelligence and adaptability.
2. Why seeking proximity to financially successful people accelerates personal growth and financial literacy.
3. How cognitive decline often shows up through subtle signs like hiding symptoms, hoarding, or double-paying bills.
4. Why caring for an aging parent requires redirecting conversations rather than constantly correcting their reality.
5. How the emotional burden of caregiving can create unique friction and stress among siblings.
6. Why traditional health insurance often fails to cover long-term memory care or cognitive decline facilities.
7. How long-term care insurance and proactive financial planning serve as essential safety nets for families.
8. Why reducing an aging parent's environment or routine can actually give them greater comfort and security.
9. How specialized veteran resources can offer critical, high-quality support for cognitive decline care.
10. Why leading through family adversity demands letting go of perfectionism and embracing vulnerability.

CHAPTER TIMESTAMPS

01:35 Meet Vivian Olden: Entrepreneurship and Proximity to Money

07:26 Growing Up Military: Developing Emotional Intelligence Through Change

13:18 Stepping Into the Sandwich Generation: Toddlers and Aging Parents

17:38 Navigating Dementia: Military Benefits and Social Work Support

21:58 Financial Red Flags, Hoarding, and Sibling Dynamic Stress

27:06 Medication Management and The Decision for Assisted Living

33:13 Understanding Care Costs, Insurance Realities, and Memory Care

42:40 Handling Behavioral Changes and Loss of Filters with Humor and Patience

53:08 Treating Parents Like Toddlers: Creating Safe and Smaller Spaces

56:37 Planning Ahead: Long-Term Care Insurance and Estate Protection

01:02:44 Closing Thoughts and Final Words

Meet Vivian Olden

Vivian Olodun is a best-selling author of Stumbling Through Adulthood, CEO of Flourish Media, keynote speaker, and marketing strategist. She is the creator of Proximity to Money, where she teaches ambitious individuals how habits, identity, and tribe dictate wealth and opportunity. Drawing from her background as a military child who attended nine schools, she leverages public relations and high emotional intelligence to help people navigate business, relationships, and financial growth

✨ Connect with Vivian Olden

🌐 Website: vivianolodun.com

💼 Substack: Proximity to Money

📚 Book: Stumbling Through Adulthood

♥️ Instagram: instagram.com/vivianolo

💼 LinkedIn: linkedin.com/in/vivianolodun

📩 Contact: [email protected]

✨ Follow Jim Fielding & Ask For An Answer

🌐Website: hijimfielding.com

♥️ Instagram:@hijimfielding

💼 LinkedIn: linkedin.com/in/jimfielding

🔗 Podcast: Ask For An Answer, available on YouTube, Apple Podcasts, and Spotify

Subscribe to Ask for an Answer on your platform of choice, and leave a review if you want more of this kind of honest, unscripted conversation.

#SandwichGeneration #EmotionalIntelligence #CaregivingJourney #FinancialLiteracy #ProximityToMoney #LeadershipPodcast #AskForAnAnswer

What happens when you trade external validation and financial success for internal alignment and emotional freedom?

Hans joins Ask for an Answer for a conversation about personal transformation, overcoming addiction, and the courage to start over. Hans spent two decades in North Carolina after moving from Germany at 25 to work in his family's veneer manufacturing business. From the outside, he seemed to have everything a person could dream of. On the inside, he felt empty, hollow, and profoundly disconnected, eventually leading to severe depression, anxiety, and an eight-year struggle with opioid addiction. Everything changed when he chose to stop running, step away from the family business, and embrace the power of plant medicine and breathwork. Now a breathwork facilitator and integration coach, Hans helps others release suppressed emotions, heal trauma, and rediscover their true purpose.

Jim and Hans explore the moments that sparked this profound shift. Hans shares how an unscripted trip to Peru for an ayahuasca ceremony shattered his expectations and showed him the path toward recovery. He discusses why letting go of control allowed him to surrender to his inner guidance and break free from addictive patterns. Hans also opens up about his recent decision to relocate his entire life back to his hometown in Germany with his wife and two children, proving that true growth requires stepping into the unknown.

IN THIS EPISODE:

• How external markers of success can mask deep internal emptiness, depression, and disconnection.
• Why real personal change occurs when the fear of remaining unchanged outweighs the fear of the unknown.
• How letting go of rigid expectations creates space for unexpected healing and personal insight.
• How somatic breathwork helps access the inner healer to process suppressed emotional pain.
• Why revisiting past trauma through conscious breathing allows people to reframe their stories and take full ownership of their lives.
• Why integration coaching, journaling, and daily habits are vital for turning emotional insights into permanent life shifts.
• How practicing radical gratitude for past hardships breaks the cycle of addiction and self-blame.
• Why trusting the process and surrendering control lowers anxiety during massive life transitions.
• How simple conscious belly breaths can serve as a daily reset tool when feeling overwhelmed or distracted.
• How authentic personal growth positively impacts immediate family dynamics and personal relationships.

CHAPTER TIMESTAMPS:

01:12 Welcoming Hans: A Major Transition Back to Germany

03:27 Moving to America at 25: Chasing Financial Success

06:43 Feeling Hollow: The Long Journey to Recognizing the Need for Change

09:18 Quitting the Family Business and Choosing Trust Over Fear

13:11 The Hidden Struggles: Opioid Addiction, Depression, and Anxiety

14:40 The Ayahuasca Experience: Dropping Expectations and Finding Inner Peace

17:35 Breaking Free: Reclaiming Curiosity, Sobriety, and Personal Growth

20:49 Discovering Somatic Breathwork as a Powerful Path to Healing

22:45 How Breathwork Sessions Work: Surrendering to the Inner Healer

31:32 Transforming Pain with Gratitude: Finding Freedom from Past Addiction

38:39 Virtual vs In-Person Breathwork: Building a Practice Across Borders

48:46 The Importance of Integration Coaching and Daily Action Steps

54:05 Closing Reflections: Leading with Curiosity, Kindness, and Awareness

Meet Hans

Hans is a breathwork facilitator and integration coach dedicated to helping individuals break free from emotional suppression, addictive patterns, and internal stagnation. After spending 20 years in North Carolina working in engineering and manufacturing, he navigated a personal recovery journey from opioid addiction, depression, and burnout through somatic breathwork, plant medicine, and self-reflection. Today, he works with clients globally, combining deep breathing practices with structured integration coaching to facilitate lasting emotional healing, self-trust, and resilience. He lives in the Black Forest region of Germany with his family.

✨ Connect with Hans Weygoldt

💼 LinkedIn: linkedin.com/in/hans-andreas-weygoldt-151777356

📱 Facebook: facebook.com/hans.whygold

✨ Follow Jim Fielding & Ask For An Answer

🌐Website: hijimfielding.com

♥️ Instagram:@hijimfielding

💼 LinkedIn: linkedin.com/in/jimfielding

🔗 Podcast: Ask For An Answer, available on YouTube, Apple Podcasts, and Spotify

How Do You Raise Capital and Build Success When the System Wasn't Built for You?

Allison Byers joins Ask for an Answer with Jim Fielding to discuss self-trust, overcoming trauma, and reclaiming power in venture capital. After walking away from corporate management consulting following a maternity leave ultimatum, Allison co-founded a medical device company out of MIT, raised nearly $10 million, and brought an FDA-registered product to market. When a Series B round stalled, an asset sale turned into a painful wake-up call. The all-male acquiring team went on to raise $55 million using her team's assets. Instead of playing the victim, Allison dived deep into capital allocation research, exposing systemic bias and founding Scroobious to level the playing field for every underrepresented founder.

Jim and Allison dig into what it truly takes to navigate inequity without losing your identity. They unpack the power of turning personal hardship into systemic change, why equity investing is a form of everyday voting, and how setting healthy boundaries protects high performers from burnout. Allison also opens up about her grassroots political work with Founders for Kamala, her role in co-authoring California's landmark Fair Investment Practices by Venture Capital Companies Law, and why entrepreneurship gave her back her professional identity.

IN THIS EPISODE:

1. How to spot and reframe real-time bias during high-stakes investment pitches.

2. Why separating your personal identity from your company protects mental health.

3. How physical burnout and stress signal the need for immediate boundaries.

4. The key differences between fiduciary venture funds and angel investor groups.

5. How groupthink inside angel networks can accidentally block funding for great ideas.

6. Why female founders deliver more profit per dollar invested despite receiving less capital.

7. How alternative funding sources can liberate founders from demoting themselves for venture money.

8. Why legislative policy and data collection are mandatory for long-term systems change.

9. How treating everyday spending and investing as voting shapes our economy.

10. Why entrepreneurship offers a vital lifeline for reclaiming professional agency.

CHAPTER TIMESTAMPS:

01:06 Welcome Allison Byers, author of Fundraising for the Rest of Us

02:40 Origin story: From management consulting to spinning out an MIT medical device

03:45 The asset sale, systemic disparities, and turning trauma into action

08:31 How historical bias shapes check-writing decisions

12:28 Identifying bias inside the room and shifting the narrative

16:50 Physical limits: Battling facial shingles from extreme stress

18:50 Healing through community, partnership, and separating self from business

22:40 Launching Scroobious in 2020 and building a movement

38:34 Why founders shouldn't dim their light for venture capital

42:28 Writing California's historic Fair Investment Practices by Venture Capital Companies Law

55:53 Why consumer dollars and investments dictate daily life

01:00:03 The final question: Why entrepreneurship matters so deeply

MEET ALLISON BYERS

Allison Byers is a founder, investor, capital access advocate, speaker, and author of Fundraising for the Rest of Us: How to Build Your Pitch, Navigate Bias, and Raise Capital on Your Terms. She is the founder of Scroobious, a relationship-first capital access platform built to scale startup growth for underestimated founders. With experience spanning corporate management consulting and medical device innovation out of MIT, Allison co-authored California’s landmark Fair Investment Practices by Venture Capital Companies Law and serves on multiple boards.

✨ Connect with Allison Byers

🌐 Website: allisonbyers.com | scroobious.com

💼 LinkedIn: Allison Byers | Scroobious

🦋 Bluesky: @apbyers.bsky.social

📸 Instagram: @apbyers | @scroobious

📚 Book: Fundraising for the Rest of Us

✨ Follow Jim Fielding & Ask For An Answer

🌐Website: hijimfielding.com

♥️ Instagram:@hijimfielding

💼 LinkedIn: linkedin.com/in/jimfielding

🔗 Podcast: Ask For An Answer, available on YouTube, Apple Podcasts, and Spotify

Subscribe to Ask for an Answer on your platform of choice, and leave a review if you want more of this kind of honest, unscripted conversation.

#LeadershipPodcast #FundraisingForTheRestOfUs #WomenInBusiness #StartupCapital #Resilience

What happens when you stop running from your past and finally claim your full story?

Dr. Joel Davis Brown joins Ask for an Answer for a deep, soul-stirring conversation about the messy reality of personal transformation, emotional growth, and what it truly means to lead an authentic life. As an awareness agent, organizational development consultant, university professor, and Chief Visionary Officer of Pneumos LLC, Dr. Joel shares how unaddressed trauma and unhealed wounds silently govern our choices until we take ownership of our narrative.

Jim and Dr. Joel unpack the subtle art of inner work. They explore why real leadership starts from the inside out, how to break free from generational patterns, and why forgiveness is a physical release rather than a quick, surface-level exercise. Dr. Joel opens up about his journey writing his latest book, reflecting on his relationship with his late father, learning to parent himself, and finding true freedom in total vulnerability.

IN THIS EPISODE:

• How claiming every part of your personal story eliminates the leverage others have over your self-worth.
• Why authentic leadership requires doing deep internal healing work before attempting to lead external organizations.
• How unaddressed emotional trauma and anger eventually bleed out onto loved ones and colleagues if left unchecked.
• Why true healing involves learning to parent yourself and stepping into full governance over your own narrative.
• How to break the cycle of generational trauma when caring for aging parents or navigating family dynamics.
• Why forgiveness is an active, physical release of bitterness that makes you lighter rather than a one-time gesture.
• How overextending yourself for others can actually be a subtle symptom of unhealed personal wounds.
• Why reframing leadership beyond corporate titles allows you to show up better in everyday personal relationships.
• How embracing complete stillness without overstimulation restores emotional energy and prevents burnout.
• Why self-acceptance and inner peace are essential prerequisites before building healthy long-term partnerships.

CHAPTER TIMESTAMPS:

00:37 Welcoming Dr. Joel Davis Brown to Ask for an Answer

01:05 What It Means to Be an Awareness Agent and Strategic Storyteller

05:28 The Inspiration Behind Souls of Queer Folk and Redefining Leadership

10:14 Embracing the Beauty and Complexity of Intersectional Human Identity

15:44 Finding Belonging, Community, and Authenticity Across Different Cities

24:09 I Had to Become the Father: Unpacking Healing, Repair, and Letting Go

31:58 Navigating Generational Trauma and Caregiving for Aging Parents

42:42 Owning Your Truth and Finding Total Freedom in Vulnerability

45:49 Redefining Family, Parenting, Mentorship, and Healthy Relationships

53:36 Prioritizing Self-Care Through Stillness and Peace

56:56 Final Thoughts and Closing Remarks

Meet Dr. Joel Davis Brown

Dr. Joel A. Davis Brown, Esq., PCC, is the Chief Visionary Officer of Pneumos LLC. As a certified leadership, life, and executive coach trained in somatic coaching, Gestalt methodology, and trauma-informed care, Dr. Joel works collaboratively with organizations, civic groups, and professionals to create synergistic cultures, breakthrough performance, and dynamic leaders. He teaches strategic storytelling at a university in France, specializes in cultural intelligence, emotional intelligence, and organizational strategy, and has spent nearly 30 years working with Startups, Non-Profits, Philanthropic Organizations, and Fortune 500 companies. He is the author of Souls of Queer Folk: How Understanding LGBTQ+ Cultural Values Can Transform Your Leadership Practice and I Had to Become the Father: The Art of Healing, Reconciliation, Repair, and Letting Go.

✨ Connect with Dr. Joel Davis Brown

🌐 Website: pneumos.com

💼 LinkedIn: linkedin.com/in/joelanthonybrown

📧 Email: [email protected]

📚 Books: Souls of Queer Folk & I Had to Become the Father

✨ Follow Jim Fielding & Ask For An Answer:

🌐Website: hijimfielding.com

♥️ Instagram:@hijimfielding

💼 LinkedIn: linkedin.com/in/jimfielding

🔗 Podcast: Ask For An Answer, available on YouTube, Apple Podcasts, and Spotify

Subscribe to Ask for an Answer on your platform of choice, and leave a review if you want more of this kind of honest, unscripted conversation.

How do you find the courage to lead with total vulnerability when the whole world expects you to stay invincible?

Dr. Julie Basler walked away from a high-profile career as a college president to help leaders reclaim their mental health, their boundaries, and their lives without losing their seat at the table. Armed with a PhD in English and decades of leadership experience, Dr. Basler is an author, speaker, and advocate who wrote her transformative book, She Is Strong Enough to Break, to break the silence around female leadership, mental health, and the burden of carrying it all alone.

What Happens When Leaders Stop Hiding Behind the Armor?

Dr. Julie Basler joins Jim Fielding on Ask for an Answer for a deeply moving conversation about emotional intelligence, personal growth, and the quiet struggles high achievers carry behind closed doors. From secretly going to therapy while running a college to sending a middle-of-the-night email to her entire campus admitting she was broken, Dr. Basler shares the moment her youngest daughter made her realize that hiding mental health struggles teaches the next generation to do the same. Jim and Julie explore how true strength comes from authenticity, why choosing kindness is a radical leadership strategy, and how breaking down opens the door to genuine healing.

IN THIS EPISODE:

• How to recognize when hiding mental health struggles sends the wrong message to those watching you.
• Why true strength requires stepping away from perfectionism and embracing vulnerability in front of your team.
• How to shift your focus from the First Mountain of ambition to the Second Mountain of servant leadership.
• Why simple, intentional acts like handwritten notes can transform how someone feels seen and valued.
• How standing up for personal values creates long-lasting ripples of courage for others.
• Why emotional intelligence and high-level leadership belong together in modern organizations.
• How reframing traffic disruptions or everyday frustration with empathy helps you realize everyone is carrying hidden pain.
• Why forgiving previous generations for their lack of mental health awareness brings personal peace.
• How embracing the role of a lifelong learner builds long-term resilience and intellectual curiosity.
• Why breaking down is often the necessary first step to breaking through into a more authentic life.

CHAPTER TIMESTAMPS:

00:00 Teaser: A Daughter's Six Words That Changed Everything

00:40 Introduction: Welcoming Dr. Julie Basler

03:48 From English PhD to College President

06:01 Leaving the Office Behind: Transitioning to the Second Mountain

10:35 The Book: She Is Strong Enough to Break

12:05 Sneaking to Therapy: The Middle-of-the-Night Email

19:40 Writing for Women in Leadership

21:35 The Dinner Table Conversation That Added an Extra Chapter

24:14 Someone Noticed Her: The Power of Handwritten Letters

31:18 Jim's Story: The Indiana University Resignation Letter

37:20 Hidden Pain: Why Everyone Is Carrying Something

41:24 25 Years Later: Going Back to College for Counseling

44:41 Research Notes vs. Tech Dashboards

55:20 Generational Trauma and Forgiving Our Parents

01:03:50 Final Words and Where to Find Dr. Julie Basler

MEET DR. JULIE BASLER

Dr. Julie Basler is an author, keynote speaker, executive mentor, and President of Strong Teams, a company dedicated to building empathy, service, and compassion in workplace culture. With nearly three decades in higher education leadership, including serving as Vice President of Academic Affairs and President of Platt College for over 18 years, Dr. Basler led her team to achieve initial nursing accreditation with ACEN, the first prelicensure BSN program at a career college to do so.

✨ Connect with Dr. Julie Basler

🌐 Website: juliebasler.com

💼 LinkedIn: Dr. Julie Basler

📚 Book: She's Strong Enough to Break: How Female Leaders Can Reclaim Their Mental Health, Their Boundaries, and Their Lives Without Losing Their Seat at the Table

✨ Follow Jim Fielding & Ask For An Answer:

🌐Website: hijimfielding.com

♥️ Instagram:@hijimfielding

💼 LinkedIn: linkedin.com/in/jimfielding

🔗 Podcast: Ask For An Answer, available on YouTube, Apple Podcasts, and Spotify

Subscribe to Ask for an Answer on your platform of choice, leave a review, and share this episode with someone who needs to hear it today.

#EmotionalIntelligence #Resilience #MentalHealthMatters #WomenInLeadership #AskForAnAnswer

What happens when a life-threatening crisis becomes your greatest catalyst for self-love, healing, and purpose?

Jenn Greenhut joins Ask for an Answer for a deeply moving conversation on mindset shifts, emotional intelligence, and finding gratitude in life’s hardest moments. A former elite USA National Team gymnast and UCLA athlete who was used to demanding perfection from her body, Jenn found herself facing rock bottom when a stage IV triple-negative breast cancer diagnosis gave her a 12 percent chance of surviving five years. Instead of seeing the news as a death sentence, a single perspective shift at her oncologist’s office helped her view the diagnosis as a gift that ultimately saved her life. Declared cancer-free just four months later, she turned her personal transformation into a mission to heal and give back. Today, she is the co-author of Everyone Needs a Larry, founder of Love, Zero Negative, and founder of The Zero Negative Foundation, supporting cancer patients, caregivers, and families through their toughest trials.

Jim and Jenn dive deep into the emotional themes that shape true resilience: shifting from asking "why is this happening to me" to "what is in this for me," replacing self-judgment with unconditional love, and trusting the journey even through trauma. Jenn shares her experience of navigating a terminal diagnosis as a newlywed, the unique bond between a patient and caregiver, and how elite sports discipline shaped her mindset during recovery. They also explore the power of staying present, managing life choices after career-altering injuries, and how simple daily anchors like her "Pinch Me" method can pull you back into gratitude.

IN THIS EPISODE:

• How shifting your mindset from punishment to protection can turn life's scariest obstacles into gifts.
• Why asking "what is in this for me" creates openness, curiosity, and emotional growth during adversity.
• How childhood trauma and high-performance pressure create toxic patterns of self-worth tied strictly to achievement.
• Why self-love and gratitude serve as powerful emotional superpowers for physical and mental healing.
• How to navigate a severe medical diagnosis as a newlywed while honoring the critical role of caregivers.
• Why trusting your medical team allows you to surrender outcome control and focus entirely on present healing.
• How elite athletic discipline provides psychological strength during personal health battles.
• Why pivoting away from a lifelong dream like the Olympics can open up unexpected new chapters of fulfillment.
• How to build an intentional brand and nonprofit foundation to support patients and caregivers.
• Why using simple tools like the "Pinch Me" method snaps you out of anxiety and grounds you in present gratitude.

CHAPTER TIMESTAMPS:

03:04 Facing a Stage IV Cancer Diagnosis and IVF Struggles

06:02 The Medical Moment That Shifted Her Perspective

08:24 Becoming Cancer-Free in Four Months Through Love and Gratitude

11:47 Turning Trauma Into Purpose and Giving Back

16:28 Writing Everyone Needs a Larry and the Caregiver Journey

21:32 Life as an Elite USA National Team Gymnast

37:33 The Sacrifices of High-Level Athletics and Personal Worth

42:40 Expanding Grants for Families and Fundraising Events

44:45 Pitching and Preparing for a TEDx Talk

48:22 Asking Better Questions and Leading With Curiosity

53:14 Jim Shares His Father’s Story With Pancreatic Cancer

01:00:15 Navigating Genetic Markers and Health Decisions

01:02:08 The Pinch Me Method for Staying Present

Meet Jenn Greenhut

Jennifer "Jenn" Greenhut is a TEDx speaker, author, and founder whose work explores healing, resilience, and transforming life's hardest challenges into opportunities for growth. After becoming cancer-free four months following a stage IV breast cancer diagnosis, Jenn dedicated her life to helping others heal. She is the co-author of Everyone Needs a Larry, founder of Love, Zero Negative, and founder of The Zero Negative Foundation, a nonprofit supporting cancer patients, caregivers, and families.

✨ Connect with Jenn Greenhut:

🌐 Website: www.lovezeronegative.com

🌐 Foundation: www.zeronegativefoundation.org

♥️ Instagram: @lovezeronegative @jenngreenhut @zeronegativeorg

💼 LinkedIn: linkedin.com/in/jennifergreenhut

🎥 TEDx Talk: TEDxRobinsonRoad - Jennifer Greenhut

✨ Follow Jim Fielding & Ask For An Answer:

🌐Website: hijimfielding.com

♥️ Instagram:@hijimfielding

💼 LinkedIn: linkedin.com/in/jimfielding

🔗 Podcast: Ask For An Answer, available on YouTube, Apple Podcasts, and Spotify

Subscribe to Ask for an Answer on your platform of choice, and leave a review if you want more of this kind of honest, unscripted conversation.

#LeadershipPodcast #EmotionalIntelligence #PersonalTransformation #Resilience #CancerSurvivor #OvercomingAdversity #MindsetShift

How do the world’s most successful leaders learn to navigate massive pressure, personal trauma, and total uncertainty?

Adam Bryant spent over a decade interviewing more than 500 CEOs for The New York Times Corner Office series. Now Senior Managing Director and Partner at The ExCo Group, Adam joins Jim Fielding on Ask for an Answer to break down what actually makes or breaks a leader when the stakes are highest. From asking executives about their childhood memories instead of their quarterly earnings to recognizing why resilience in the face of early adversity is the ultimate differentiator, Adam brings decades of journalism experience and human insight into one powerful conversation.

The two reflect on why leading today is harder than ever before and how authentic leadership means closing the gap between how you want to be perceived and how people actually decode you. Adam explains why so much traditional leadership advice falls short when real human beings are brought into the equation. The conversation wraps up with a sharp look at why active listening is the ultimate underrated superpower for anyone trying to build real trust and followership.

KEY TAKEAWAYS:

• How early life adversity, family dynamics, and personal setbacks shape the internal drive needed for executive success.
• Why birth order and childhood expectations heavily influence your default leadership style and team management habits.
• How to manage the control-freak instinct that gets you promoted before it burns you out.
• Why your greatest professional strength can easily double as your biggest weakness without deep self-awareness.
• How to close the gap between how you want people to perceive you and how they actually decode your actions.
• Why practical human wisdom beats rigid, cookie-cutter leadership theories every single time.
• How to build psychological safety in remote or hybrid teams by intentional effort toward creating a sense of us.
• Why admitting you do not have all the answers creates stronger solutions from your entire team.
• How active listening serves as a foundational superpower containing humility, curiosity, and respect.
• Why processing information rather than just hearing it transforms surface conversations into real connection.

CHAPTER TIMESTAMPS:

03:26 The Origin of Corner Office: Asking CEOs About Their Childhoods

05:54 The Three Opening Questions That Uncover Real Vulnerability

10:25 Indicators of Success: Why Early Adversity Drives High Achievers

15:10 Unpacking Sibling Order, Family Expectations, and Leadership Traits

17:39 Deprogramming Control Freak Tendencies to Avoid Burnout

25:46 Starting at the Bottom: Adam’s 30-Year Journey in Journalism

29:27 The Pivot to Executive Mentoring at ExCo Leadership Group

31:09 Why Most Cookie-Cutter Leadership Theories Fail in Practice

37:44 The Dual Challenge of Modern Leadership: Authenticity and Pressure

41:39 Navigating Hybrid Work Culture and Building Real Team Connection

51:42 The Underrated Leadership Superpower: Active Listening

Meet Adam Bryant

Adam Bryant is a veteran journalist, author, speaker, and Senior Managing Director and Partner at The ExCo Group. Across his 30-year career in journalism, including two stints at The New York Times, he interviewed more than 1,000 CEOs and board directors and created the renowned Corner Office column. He has authored four books on leadership, including The Corner Office and The CEO Test, focusing on practical, actionable insights for modern leaders navigating complex human dynamics.

✨ Connect with Adam Bryant

🌐 Website: excoleadership.com

💼 LinkedIn: linkedin.com/in/adambryantleadership

📚 Books: The CEO Test, The Corner Office, Quick and Nimble, Jump-Start Your Career

✨ Follow Jim Fielding & Ask For An Answer:

🌐Website: hijimfielding.com

♥️ Instagram:@hijimfielding

💼 LinkedIn: linkedin.com/in/jimfielding

🔗 Podcast: Ask For An Answer, available on YouTube, Apple Podcasts, and Spotify

Subscribe to Ask for an Answer on your favorite platform, and leave a review to help us bring you more honest, unscripted conversations!

#LeadershipPodcast #EmotionalIntelligence #Resilience #ExecutiveCoaching #ActiveListening

What Happens After 31 Conversations With Extraordinary Leaders?

After an unforgettable second season of Ask for an Answer, Jim Fielding steps behind the microphone alone to reflect on the biggest lessons that emerged from 31 conversations with CEOs, creatives, public servants, founders, athletes, journalists, and changemakers.

This isn't a highlight reel. It's a deeply personal look at what changed Jim's own thinking about leadership, curiosity, and what it really means to ask better questions.

Drawing on conversations with guests like Jeremy Hobson, Olivia Jordan, Marie Harf, Gerardo Celasco, Ryan Stana, and Brad Stulberg, Jim shares the three ideas that kept resurfacing all season—and why they've become the foundation of his next book.

More importantly, he explains why leadership isn't about having the right answers. It's about creating the conditions where better questions can be asked.

What Are the Three Lessons Every Leader Needs?

Jim explores how the best leaders don't walk into a room trying to win—they walk in ready to learn. He reflects on why asking honest questions always comes with personal risk, why consistency matters more than breakthrough moments, and why kindness isn't soft leadership. It's one of the strongest leadership strategies we have.

He also shares a personal update, including why he's taking a short break from the podcast to finish his second book and what's coming in Season 3 of Ask for an Answer.

Whether you've listened to every episode or you're discovering the show for the first time, this conversation captures what the podcast has always been about: curiosity, humanity, and leading with intention.

KEY TAKEAWAYS

• Why the best leaders enter conversations ready to learn, not ready to win.
• How asking better questions creates stronger teams, deeper trust, and better decisions.
• What Jeremy Hobson, Olivia Jordan, Marie Harf, Ryan Stana, Brad Stulberg, and Gerardo Celasco taught Jim about modern leadership.
• Why clarity is an act of kindness, especially during difficult conversations.
• How consistency—not breakthrough moments—is what actually builds meaningful work.
• Why leaders should stop performing and start listening.
• The leadership philosophy behind Jim's upcoming second book.
• Why rest isn't the reward for great work—it's part of doing great work.
• What listeners can expect from Season 3 of Ask for an Answer.

Follow Jim Fielding & Ask For An Answer

Website: hijimfielding.com

Instagram: @hijimfielding

LinkedIn: James (Jim) Fielding

Podcast: Ask For An Answer on YouTube, Apple Podcasts, and Spotify

Community: LeagueOfRadicalKindness.com

If this episode reminded you that leadership starts with better questions, subscribe to Ask for an Answer and leave a review. It helps more curious leaders discover the show.

CHAPTER TIMESTAMPS

00:00 Welcome to the Season 2 Recap

01:15 Lesson One: How You Walk In Changes the Room

03:05 Lesson Two: The Questions That Cost You Something

05:00 Lesson Three: What You Keep Is What You Become

07:00 The Leadership Philosophy Behind Jim's Next Book

09:10 Gratitude for Season 2's Guests and Community

10:45 Why Jim Is Taking a Short Break

12:15 Inside the League of Radical Kindness

13:15 Season 3 Preview: What's Coming Next

14:30 Final Reflections: Why Questions Still Matter Most

What does authentic leadership look like in a world that's more divided than ever? How do you have meaningful conversations with people who see the world completely differently? And what happens when democracy itself is being tested?

In the final guest episode of Season 2 of Ask for an Answer, Jim Fielding sits down with foreign policy expert, political analyst, and University of Pennsylvania executive director Marie Harf for a candid conversation about leadership, civic responsibility, and why engaging across differences matters now more than ever.

Drawing on her experience at the CIA, the U.S. State Department, and nearly a decade as a Democratic political analyst on Fox News, Marie shares what she's learned about communicating across political divides, America's changing role on the global stage, and why thoughtful disagreement is essential to a healthy democracy.

Together, Jim and Marie explore the challenges facing the Democratic Party ahead of the 2026 midterms and 2028 presidential election, the qualities the next generation of leaders will need, and why hope, curiosity, and community remain powerful forces during uncertain times.

Whether you're passionate about politics, interested in leadership, or simply looking for a thoughtful conversation about where we go from here, this episode offers perspective without sacrificing nuance.

In this episode, you'll learn:

• Why America's role in the world is changing and what it means for the future
• How to have productive conversations with people you fundamentally disagree with
• The leadership qualities the next generation of political leaders will need
• Why democracy depends on participation, not perfection
• How radical kindness, curiosity, and community can bridge even our deepest divides

00:00 Why Democracy Depends on Better Conversations

03:15 Marie Harf's Journey from the CIA to Fox News

08:05 America's Changing Role in the World

18:20 Inside Fox News: Finding Common Ground Across Political Divides

31:00 What Democrats Need to Learn Before the Next Election

42:15 The Leaders to Watch for 2028

50:00 Why Democracy Requires More Than Winning Elections

54:30 Hope, Civic Responsibility, and Building a Better Future Together

Meet Marie Harf

Marie Harf is a former CIA analyst and State Department Deputy Spokesperson who has spent her career at the intersection of foreign policy, national security, and public communication. She is the Executive Director of Perry World House at the University of Pennsylvania and has been a Democratic political analyst on Fox News for nearly a decade, where she brings thoughtful perspective to some of the country's most important conversations about democracy, leadership, and America's role in the world.

Instagram: @marieharf

LinkedIn: Marie Harf

Follow Jim Fielding & Ask For An Answer:

Website: hijimfielding.com

Instagram:@hijimfielding

LinkedIn: James (Jim) Fielding

If this conversation resonates with you, subscribe to Ask for an Answer, leave a review, and share this episode with someone who believes better conversations can lead to a better future.

#LeadershipPodcast #Democracy #PoliticalLeadership #ForeignPolicy #CivilDiscourse

Leslie Grandy worked for James Cameron and Brian De Palma, then walked away from Hollywood at 35 to start over as the most junior person on a tech team. That decision led to Apple, Amazon, T-Mobile, and a career built on one belief: you can figure it out.

What Happens When You Stop Waiting for Permission to Pivot?

Leslie Grandy joins Ask for an Answer for a freewheeling conversation about self-trust, reinvention, and why creative confidence matters more than ever in the age of AI. A Northwestern film graduate who earned her way into the Directors Guild of America with no industry connections, Leslie built a successful Hollywood career before realizing the lifestyle would cost her the relationship and the life she actually wanted. So she got an MBA, took an entry-level product role, and rebuilt from scratch. That second act took her through Visio's billion-dollar sale to Microsoft, the first Android phone launch at T-Mobile, and product leadership roles at Apple, Best Buy, Discovery, and Amazon.

Jim and Leslie dig into what made the pivot work: choosing what you're moving toward instead of running from what isn't working, trusting your own judgment over external approval, and having the humility to swallow your ego when starting over. Leslie shares the story of applying to exactly one college, early admission only, because she believed she'd get in. She did.

Can You Stay Creative When AI Does the Thinking for You?

The conversation turns to Leslie's award-winning book, Creative Velocity: Propelling Breakthrough Ideas in the Age of Generative AI. Leslie makes the case that creativity isn't a talent you're born with. It's a capacity everyone carries and most people abandon, especially now, when a machine can hand you polished output with no soul behind it. She and Jim talk about using AI as a thinking partner rather than a replacement, why leaders must build environments where teams believe they can solve unfamiliar problems, and how curiosity connects directly to the Ask for an Answer philosophy of leading with questions instead of certainty.

The episode closes with a candid look at redefining retirement. Leslie's definition is simple: never doing anything she doesn't want to do. From teaching executive education at the University of Washington to planning a life with a husband 22 years her senior, she shows what it looks like to design your time around joy, vitality, and learning. Her answer to Jim's final question, what she'd tell her younger self, is one every high achiever needs to hear.

KEY TAKEAWAYS

1. How to know when a career pivot is right by identifying what you're moving toward instead of what you're escaping.
2. Why creative confidence, not raw talent, determines who solves unfamiliar problems and who runs from them.
3. How to use generative AI as a thinking partner without surrendering the human creativity that gives work meaning.
4. Why starting over at a lower level requires ego management, and how self-belief makes the trade worth it.
5. How prioritizing a core relationship can clarify major career decisions instead of complicating them.
6. Why leaders who admit they don't have all the answers draw better solutions from their teams.
7. How curiosity and the willingness to say "I don't know how this works yet" build durable self-confidence.
8. Why the best answers in a room often come from the most junior or unexpected voices.
9. How to define retirement as freedom of choice rather than the absence of work.
10. Why going easier on yourself may be the most important leadership lesson high performers learn too late.

CHAPTER TIMESTAMPS

00:00 Introduction: Welcoming Leslie Grandy

02:18 From Northwestern Film School to the Directors Guild

03:14 The Pivot: An MBA and a Billion-Dollar Startup Exit

06:01 The Two Moments That Made Leaving Hollywood Clear

08:12 Choosing a Relationship Over Industry Stature

09:57 Self-Approval Instead of External Validation

11:03 Starting Over at 35 and Managing the Ego

13:22 Building Self-Trust Without Role Models

16:11 Betting on Herself: The One-School College Application

21:55 A Totaled Car and the Problem-Solver Instinct

26:45 Why Leslie Wrote Creative Velocity

28:51 Protecting Human Creativity in the Age of AI

32:07 Curiosity as the Foundation of Creative Confidence

34:17 Why Leaders Don't Need All the Answers

36:50 Redefining Retirement: Only Doing What Brings Joy

41:36 Planning Life and Retirement With a 22-Year Age Gap

43:19 Money, Timing, and the Freedom to Choose

49:35 Aging, Vitality, and the Morning Body Inventory

54:32 Ask for an Answer: What Leslie Would Tell Her Younger Self

56:46 Closing Thoughts

Meet Leslie Grandy

Leslie Grandy is a product executive, speaker, and CEO advisor who spent 25+ years leading first-to-market products at Apple, Amazon, T-Mobile, Best Buy, and Discovery after an early career in film as a Directors Guild of America assistant director for Brian De Palma and James Cameron. She's the author of Creative Velocity: Propelling Breakthrough Ideas in the Age of Generative AI (Wiley), founder of The Product Guild, and an executive educator at the University of Washington's Foster School of Business.

✨ Connect with Leslie Grandy

🌐Website: lesliegrandy.com

💼 LinkedIn: Leslie Grandy

📚 Book: Creative Velocity: Propelling Breakthrough Ideas in the Age of Generative AI

✨ Follow Jim Fielding & Ask For An Answer:

🌐Website: hijimfielding.com

♥️ Instagram:@hijimfielding

💼 LinkedIn: James (Jim) Fielding

🔗 Podcast: Ask For An Answer, available on YouTube, Apple Podcasts, and Spotify