Best Debbie Weiss Podcasts (2025)

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Ep. 136: Is Gratitude Just A Buzzword? 16:03

1d ago16:03

16:03

Send us a text This episode wasn’t planned. But sometimes, the unscripted moments are the ones that need to be shared most. After a powerful workshop and a walk with my dog that turned into something way more reflective than expected, I found myself thinking about all the ways I used to roll my eyes at the idea of “gratitude.” I thought it was fluf…

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Finding Meaning Through Caregiving, Loss, and Writing with Nickolas Butler 1:05:25

1h ago1:05:25

1:05:25

In this episode, Nickolas Butler explores finding meaning through caregiving, loss, and writing. At just 20 years old, Nick became his father’s legal guardian after a sudden brain aneurysm — a role he held for 23 years. What began as a family emergency became a long, complex journey that shaped his identity, his values, and his voice as a novelist.…

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How to Quiet the Inner Critic and Finally Get Unstuck with Michelle Chalfant 59:06

2d ago59:06

59:06

In this episode, Michelle Chalfant explores how to quiet the inner critic and finally get unstuck. She has spent 25 years developing practical tools for working with what she calls the other wolf. Michelle explains why most of us are making decisions from the emotional age of about 13. And she’ll give you the exact process for transforming triggers…

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From Divorce to Discovery: Nature’s Wisdom for Life’s Transitions with Lyanda Haupt 1:05:29

6d ago1:05:29

1:05:29

In this episode, Lyanda Haupt shares her journey from divorce to discovery and nature's wisdom for life's transitions. She challenges everything you might think you know about hope, about walking barefoot on the earth, and what it actually means to feed the good wolf. Discover the six hidden saboteurs that quietly derail your best intentions—like a…

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Why We Resist Change (and What to Do About It) with Ross Ellenhorn 55:06

10d ago55:06

55:06

In this episode, Ross Ellenhorn explores the complexities of why we resist change and what to do about it. As Ross explains in this conversation, “staying the same protects you from the insult of small steps.” He shows us why these tiny steps can sometimes feel insulting and demoralizing. Ross also delves into the fear of raising expectations, the …

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How to Create Change at Work Without Losing Yourself with Melody Wilding 1:03:17

14d ago1:03:17

1:03:17

In this episode, Melody Wilding discusses how to create change at work without losing yourself. She challenges the idea that you’re powerless at work, even in tough cultures. If you’ve ever wondered how to navigate office politics, or if there’s a way to work with integrity even when you’re not in charge, this conversation will give you both practi…

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Ep. 135: When's The Last Time You Felt Like You? 22:00

17d ago22:00

22:00

Send us a text In this episode, I open up about something deeply personal: what it felt like to completely lose myself while caring for everyone else. I share the moment I realized I had become disconnected from my joy, my identity, and even my laugh. Maybe you’ve felt it too, that quiet sense of going through the motions, showing up for everyone b…

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Can Radical Hope Save Us from Despair in a Fractured World? with Jamie Wheal 1:02:42

17d ago1:02:42

1:02:42

In this episode, Jamie Wheal explores the question of “Can radical hope save us from despair in a fractured world?” He argues that most of the feel-good positivity we are sold is useless when facing real crises, from climate collapse to meaninglessness. But there is a kind of hope that survives contact with brutal reality. Get Weekly Bites of Wisdo…

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Is Stress Speeding Up Your Aging? What You Can Do About It Today with Elissa Epel 33:29

21d ago33:29

33:29

In this episode, Elissa Epel explores how stress can speed up aging and what you can do about it. She explains telomeres, which are those protective caps on our chromosomes, shorten with stress and poor habits, speeding up aging and disease. She also delves into the science of how thought patterns, diet, and even our response to daily challenges ca…

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Ep. 134: Mid-Year Check In! 20:18

24d ago20:18

20:18

Send us a text We’re halfway through the year, can you believe it? In this episode, I’m doing a personal mid-year check-in and inviting you to do the same. No pressure, no perfection, just an honest look at where we are, what’s worked, what hasn’t, and where we want to go next. I’ll walk you through a simple reflection exercise to help you refocus …

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From “Why Me?” to “What Now?”: A New Approach to Pain and Growth with Scott Barry Kaufman 56:56

24d ago56:56

56:56

In this episode, Scott Barry Kaufman challenges us to go from asking ourselves “Why Me?” to “What Now?” as he unpacks a new approach to pain and growth. Scott explains how the real work happens in the messy middle as we unpack the dangers of black and white thinking, and why genuine change isn’t about a single epiphany, but a thousand small choices…

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Purposeful Living: Strategies to Align Your Values and Actions with Victor Strecher 1:04:18

28d ago1:04:18

1:04:18

In this episode, Victor Strecher discusses purposeful living and strategies to align your values and actions. Vic shares his imperfect journey back to meaning and to living for what matters most after losing his daughter. He explores what it means to be purposeful versus just having a purpose, how energy and vitality play a role in living out our v…

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Ep. 133: Finding Peace In Your Own Company 12:14

1M ago12:14

12:14

Send us a text This weekend, I had the rare experience of being completely alone—no kids, no plans, just me and my dog Yogi. And I’ll admit, at first, that old familiar feeling crept in… the fear that being alone might turn into feeling lonely. But what I discovered was the opposite. I felt grounded, centered, and deeply connected to myself. In thi…

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Escape the Goal Trap: Embrace Curiosity and Tiny Experiments with Anne-Laure Le Cunff 54:40

1M ago54:40

54:40

In this episode, Anne-Laure Le Cunff, discusses how to go from procrastination to action using the power of tiny experiments. Most advice about self-improvement assumes you know where you’re going, but what if you don’t? Anne-Laure suggests that’s not a flaw, it’s actually the starting point. Her new book, Tiny Experiments, offers a way to explore …

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The Hidden Cause of Procrastination and How to Finally Move Forward with Taylor Jacobson 52:32

1M ago52:32

52:32

In this episode, Taylor Jacobson discusses the hidden cause of procrastination and how to finally move forward in your life. He explores how transformation rarely feels graceful, how repressed emotions shape our behavior, and what it takes to live a life true to your inner compass. It’s a vulnerable, grounded conversation about fear, reinvention, a…

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Ep. 132: Let's Talk About Regret 18:59

1M ago18:59

18:59

Send us a text We’ve all had those “if only I had…” moments. In this episode of the Maybe I Can® Podcast, I open up about my own experiences with regret, including stories from my dad’s life and the final weeks with my husband, and how those moments shaped me. Regret can weigh us down, but it doesn’t have to keep us stuck. Let’s talk about how to m…

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The Quiet Pain of Self-Loathing and Finding the Courage to Face It with Sarah Gormley 1:02:08

1M ago1:02:08

1:02:08

In this episode, Sarah Gormley discusses the quiet pain of self-loathing and finding the courage to face it. Sarah had it all – a thriving corporate career, success, and admiration. But beneath was a quiet, relentless self-loathing she couldn’t shake. In her memoir, The Order of Things, Sarah shares the profound turning point at 40 when she finally…

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Why We Stop Noticing What Matters and How to Feel Alive Again with Tali Sharot 1:01:35

1M ago1:01:35

1:01:35

In this episode, Tali Sharot explains why we stop noticing what matters and how to start feeling alive again. She describes what habituation is and how our minds normalize what once moved us. Tali also explores ways that we can reawaken joy, purpose, and even moral clarity. It’s an eye-opening look at the subtle ways we lose and then can reclaim ou…

1
Ep. 131: Why Are We So Hard On Ourselves? 21:48

1M ago21:48

21:48

Send us a text In this episode of the Maybe I Can® Podcast, I’m getting real about something many of us struggle with: being our own worst critic. After giving a keynote speech that left me on a high, I received the photos and video — and immediately started picking myself apart. Sound familiar? We’ll dive into: ✨ Why our inner critic shows up (esp…

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Ancient Wisdom Meets Modern Life: Finding Ease and Clarity with Charlie Gilkey 51:44

2M ago51:44

51:44

You're doing everything right, staying productive, chasing growth, keeping up. But what if the discomfort you feel isn't a sign that you need to do more, but a signal to let go? In this episode, Charlie Gilkey and I explore the Tao Te Ching, which is one of my favorite books of all time, but not as a relic from the past, but as a guide for navigati…

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How to Recognize the Hidden Signs of Burnout with Leah Weiss 57:56

2M ago57:56

57:56

What if the very thing that gives your life meaning is also what's burning you out? That's the paradox. Leah Weiss found herself in teaching compassionate leadership at Stanford. Working with organizations inspired by the Dalai Lama. Doing the kind of work most of us dream of. And yet she was falling apart. In today's conversation, we unpacked the …

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Ep. 130: The Dreams We Leave Behind 25:56

2M ago25:56

25:56

Send us a text What if you haven’t outgrown your dreams—just drifted away from them? In this episode, we explore what happens when we stop dreaming. As we grow older, it’s easy to trade bold aspirations for practical realities. Maybe someone told you your dream was unrealistic. Maybe life just got busy. But here’s the truth: 92% of people never pur…

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The Nobility of Service: Finding Magic and Connection in the Smallest Gestures with Will Guidara 1:00:34

2M ago1:00:34

1:00:34

What do a fine dining maitre d. A magician burying cards in a backyard and a toddler looking for Elsa have in common? They all show us that magic still exists. If we’re willing to care more, than seems reasonable. In this episode, Will Guidara, who’s a former co-owner of 11 Madison Park, which was once named the best restaurant in the world, the au…

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Embrace the Chaos: Finding Clarity Through Meditation with Henry Shukman (Part 2) 1:00:08

2M ago1:00:08

1:00:08

In part one of this two-part conversation, we walked along the edge of paradox where effort gives way to ease and the search itself becomes the obstacle. In this second part of my conversation with Zen teacher Henry Shukman, the way begins to reveal itself, not as something we grasp, but something we live. We talk about awakening, the collapse of s…

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Ep. 129: 5 Hints for Taking Action 19:25

2M ago19:25

19:25

Send us a text In today’s episode of the Maybe I Can podcast, we’re diving into something so many of us struggle with: taking action. We have dreams, plans, and to-do lists… but often we get stuck waiting for the “perfect” moment. That stops today. I’m sharing 5 simple and powerful hints to help you finally move forward, even if you’re not ready, e…

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Embrace the Chaos: Finding Clarity Through Meditation with Henry Shukman (Part 1) 1:00:25

2M ago1:00:25

1:00:25

In this episode, Henry Shukman discusses how to embrace the chaos and find clarity through meditation while exploring themes of self-development and self-love. Henry emphasizes the balance between effort and acceptance in spiritual practice, highlighting the interplay between sudden insights (satori) and gradual progress. He also discuss the import…

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Navigating Fear and Hope: the Everyday Courage That Shapes Our Lives with Ryan Holiday 52:41

2M ago52:41

52:41

In this episode, Ryan Holiday explores navigating fear and hope and the everyday courage that shapes our lives. He unpacks how to confront our fears and how we need to do so, over and over. With great stories and insights, we are reminded that we don’t have to be fearless, we just have to begin. Key Takeaways: The concept of courage and its signifi…

1
Ep. 128: Embracing Life's Unseen Transitions 22:45

2M ago22:45

22:45

Send us a text I wasn’t expecting to attend my son’s college graduation alone. But there I was—proud, emotional, and deeply aware of who was missing. In this episode of the Maybe I Can podcast, I share what it felt like to face a moment that should’ve been joyful… but also brought up grief and reflection. Life has a way of shifting underneath us—so…

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Failure as Fertilizer: Learning to Bloom Again with Debbie Millman 59:56

2M ago59:56

59:56

In this episode, Debbie Millman explores how we can use failure as fertilizer and learn to bloom again. Debbie's book and this conversation is about more than just gardening tips or tools, it's about what happens when we let ourselves be bad at something, especially later in life. Debbie opens up about learning to grow and why failure might be the …

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Reinvention at Any Age: Lori Pappas on Wisdom, Resilience & Saying Yes to Life 42:03

2M ago42:03

42:03

In this inspiring episode, I’m joined by the remarkable Lori Pappas, who shares her extraordinary journey of personal and professional reinvention. Now in her 70s, Lori reflects on why this might just be the best decade of her life. From breaking through early career challenges in a male-dominated industry to spearheading meaningful projects in Eth…

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From Benches to Breakthroughs: A New Approach to Mental Health with Dixon Chibanda 54:52

2M ago54:52

54:52

In this episode, Dr. Dixon Chibanda explores from benches to breakthroughs: a new approach to mental health. He explains why storytelling, radical empathy, and solving daily-life problems often outperform medication-first approaches; how three simple steps—opening the mind, uplifting, strengthening—turn elders into community healers; and why hope, …

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Ep. 127: Turning Pain Into Purpose with Lena Wilson 37:28

2M ago37:28

37:28

Send us a text In today’s powerful episode, I’m joined by the incredible Lena Wilson—a speaker, coach, and compassionate guide for women navigating life after loss, divorce, and major life transitions. Lena shares her deeply personal journey of rediscovering who she was after the end of her marriage, and how she learned to embrace her own voice, de…

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Beyond Anxiety: How Curiosity Turns Fear Into Fuel with Martha Beck 58:00

2M ago58:00

58:00

In this episode, Martha Beck explores how to move beyond anxiety and how curiosity turns fear into fuel. Martha dives into why anxiety can’t simply be silenced. It has to be replaced with things like creativity, curiosity, and a deep kindness towards ourselves. Key Takeaways: Discussion of anxiety versus fear and their psychological implications. E…

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Move Your Body, Free Your Mind: The Science of Movement and Mental Health with Caroline Williams 1:07:20

3M ago1:07:20

1:07:20

In this episode, Caroline Williams shares how moving your body can free your mind as she dives into the surprising science of movement and mental health. Caroline spent years studying the brain until she realized she was ignoring half the equation. She explains how movement of all kinds, walking, stretching, dancing, and even laughter can reshape o…

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Ep. 126: The Weight Of Unfinished Things 19:05

3M ago19:05

19:05

Send us a text Have you ever felt totally drained before your day even starts? I’ve been there—and it turns out, the biggest energy zapper isn’t always what we think. In this episode, I’m sharing how things like clutter, unfinished tasks, and all those mental “to-dos” can quietly weigh us down and keep us stuck in survival mode. From unpacked boxes…

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Navigating the Messy Parts of Life: Embracing Imperfection and Growth with Josh Radnor 50:14

3M ago50:14

50:14

In this episode, Josh Radnor discusses the messy parts of life and embracing imperfection and growth. Josh Radnor explains how, even outward success, fame, acclaim, creative fulfillment isn’t enough to quiet the deeper battles within. He shares how real freedom comes not from achieving perfection, but from making peace with the messy, unfinished pa…

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Why Community and Courage Matter More Than Ever with Laura McKowen 58:14

3M ago58:14

58:14

In this episode, Laura McKowen explores why community and courage matter more than ever in making change in your life. She dives into the “messy midle” – theu ncertain space between giving up what umbs us and becoming someone new. She shares the story of the Luckiest Club, a global sobriety community. Key Takeaways: Understanding that real transfor…

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Ep. 125: 3 Milestones That Rewrote My Life 27:02

3M ago27:02

27:02

Send us a text In this heartfelt episode, I reflect on three significant anniversaries in my life: the 30th anniversary of my insurance agency, the 2nd anniversary of my 'Maybe I Can' podcast, and what would have been my 31st wedding anniversary with Gary. I share the struggles and self-doubt I faced when starting my podcast and how I overcame them…

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Anxiety, Beauty, and the Unknown: A Map to Emotional Resilience with David Whyte 57:53

3M ago57:53

57:53

In this episode, David Whyte explores anxiety, beauty, and the unknown as a true map to emotional resilience. David shares how anxiety can be a doorway to deeper understanding and connection. He and Eric discuss the paradox of holding both joy and struggle, the surprising wisdom hidden in everyday emotions, and how poetry and language can bring us …

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Unlock Your Inner Anthem: A Tribute to Mike Peters 38:07

3M ago38:07

38:07

This is a special episode from our archives with one of my favorite musicians, Mike Peters. Mike recently passed away, and this episode is more than a conversation; it’s a tribute to a beautiful soul. In our chat, we explored the idea of our lives being anthems; how defiance, hope, and inner strength were a soundtrack for his formative years, and l…

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Ep. 124: No One Is Coming To Save You 20:12

3M ago20:12

20:12

Send us a text Hi, I'm Debbie Weiss and in this episode of the Maybe I Can podcast, we delve into the empowering realization that no one is coming to save you. While it might sound harsh, it's incredibly liberating. I share my personal journey and examples of when I expected someone or something to change my life. Whether it's waiting for the right…

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Fluke or Fate? Embracing Uncertainty to Live a Fuller Life with Brian Klaas 56:53

3M ago56:53

56:53

In this episode, Brian Klaas explains the concept of whether things are a fluke or fate, and explores how embracing uncertainty can lead to a living a fuller life. Brian makes the case that randomness and chaos might be exactly what makes our lives matter so much, and how we tend to worship at the “Altar of Progress in the Church of Control.” We ma…

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'Maybe I can' with Debbie R Weiss 42:57

3M ago42:57

42:57

In this inspiring episode, I chat with Debbie Weiss, who, at 50, decided it was time to stop living for everyone else and start asking, “Maybe I can?” Following the loss of her husband, Debbie transformed her grief into growth and began sharing her journey to encourage others to do the same. We talk about reclaiming identity after loss, writing her…

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The Bittersweet Truth About Beauty, Sorrow, and What Makes Life Worth Living with Susan Cain 51:55

3M ago51:55

51:55

In this episode, Susan Cain explores the bittersweet truth about beauty, sorrow, and what makes life worth living. She emphasizes the transformative power of music and bittersweet emotions and also discusses how acknowledging grief can lead to deeper connections and creativity. This episode encourages listeners to embrace their emotions and seek be…

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Ep. 123: Why Rest is a Superpower 28:23

3M ago28:23

28:23

Send us a text In this episode of the Maybe I Can Podcast, I’m talking about something that doesn’t come easy to many of us—giving ourselves permission to rest. After a recent vacation in Punta Cana, I noticed a big shift in myself: I was finally able to unplug and truly relax. Meanwhile, my cousins stayed constantly busy, and it really made me ref…

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Flaws as Fuel: Harness Doubt, Cynicism & Ambition for Real Growth with Claire Hoffman 51:23

3M ago51:23

51:23

In this episode, Claire Hoffman explores the idea behind how our flaws, doubt, cynicism, and even ambition aren’t signs of failure, but can be used as fuel. She tells the story of Aimee Semple McPherson, a woman who built a religious empire and faked her own kidnapping. But this episode isn’t about scandal. It’s about the tension that we all carry …

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The Midlife Makeover: Redefining Success and Happiness After 40 with Chip Conley 45:44

4M ago45:44

45:44

In this episode, Chip Conley defines a midlife makeover and how to redefine success and happiness after 40. He shares how the most difficult stretches of his life ended up being the start of something completely new. Chip also explains the pull of the ego, the search for identity and how letting go of traditional success can open the door for somet…

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Ep. 122 5 Powerful Lessons Grief Has Taught Me 25:23

4M ago25:23

25:23

Send us a text In this episode, I’m sharing five powerful lessons I’ve learned since becoming a widow. While my journey is uniquely mine, I believe these lessons are universally relatable for anyone navigating through loss or major life transitions—whether it’s from divorce, becoming an empty nester, retiring, or experiencing another shift in life.…

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How to Nurture Creativity in a Noisy World with Maggie Smith 1:03:42

4M ago1:03:42

1:03:42

In this episode, Maggie Smith explores how to nurture creativity in a noisy world. A lot of people think creativity is something you do with a paintbrush or a poem but Maggie challenges us to think differently about creativity. It isn’t about what you make, but how you live. She dives into what it really means to be creative, even when you’re overw…

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From Loneliness to Belonging: Small Steps That Change Everything with Jillian Richardson 52:38

4M ago52:38

52:38

In this episode, Jillian Richardson discusses the journey from loneliness to belonging and shares the small steps that can change everything. She delves into why friendship takes more effort than we expect and how we can actually get better at it. Jillian also explores what gets in the way of connection, why it’s not just about putting yourself out…

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Debbie Weiss Podcasts

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