The Sincerely Show

Some conversations change you. This is one of those shows.Each week, Katherine Dudtschak sits with someone who has lived a life worth examining: leaders who rebuilt everything, people who told the truth when silence would have been easier, humans who found their way home to themselves.Katherine spent thirty-seven years in financial services and in 2019 came out publicly as one of Canada's most senior banking executives. She knows what honesty costs. That knowing makes her a remarkable witness.Unhurried. Unscripted. True.

The Sincerely Show is a education podcast hosted by Katherine Dudtschak, with 19 episodes on record and a Required Pod Score of 80.

Katherine Dudtschak hosts The Sincerely Show, a education show with 19 episodes published.

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  Episode #20

  Carlos Delgado and Craig Alexander: The Simplicity of Chaos, and Carrying Beauty Home

  Oct 1, 202655 minS1

  Connect with Katherine Dudtschak Website: Sincerely Inc. LinkedIn: Katherine Dudtschak Instagram: @kdudtschak Connect with Carlos Delgado Website: Carlos Delgado LinkedIn: Carlos Delgado Instagram: Carlos Delgado Connect with Craig Alexander Website: Sybil Frank Gallery LinkedIn: Craig Alexander Instagram: Sybil Frank Gallery Carlos Delgado and Craig Alexander: The Simplicity of Chaos, and Carrying Beauty Home Carlos Delgado grew up in the mountains of Colombia where finding paper to draw on was near impossible. Today he mentors nine young artists in his Colombian studio, provides their materials and space, sells their work internationally, and runs Arte Espiral, an organisation that delivered ninety art workshops to indigenous children in mountain communities last year. Craig Alexander is the founder and owner of Sybil Frank Gallery in Wellington, Prince Edward County, named for his two grandmothers, a place he describes as a happy maker, open and free to anyone who walks through the door. This conversation began inside a live painting performance at the gallery, Carlos working with a knife more than a brush while Craig and Katherine spoke. It walks backward through how Craig found Carlos online and sold his first painting within a week; through Carlos's fifteen years in Canada riding the Toronto subway and reading the tired faces of rush-hour commuters; and through the day a young artist named Eleazar arrived at Carlos's studio with an oil painting on cheap paper because he could not afford canvas. His style, the simplicity of chaos, where apocalyptic strokes resolve into beauty and love, runs through everything. This episode is for anyone who has wondered whether the thing that once saved them can become the thing they give away. Key Moments - The afternoon Eleazar appeared at Carlos's studio door: six weeks of work, a hundred dollars earned, and an oil painting on cheap paper because he could not afford canvas, which moved Carlos to offer him space, materials, and a place beside him to work. - Craig describing the gallery named for his grandmothers: the rooms, the art he pairs across different artists so everything works as one, and his conviction that it is a happy maker rather than a moneymaker. - Carlos's wish for the world: balance and dignity, with art doing its part. Quotes to Remember "I didn't have money to buy canvas. And I was loyal so touched. I told my wife, look, he's so talented, but he doesn't have at least a canvas to do a painting." Carlos Delgado "It's not a moneymaker. It's it's It's a happy maker." Craig Alexander Reflection for Listeners There is a moment from this conversation that I have been sitting with: I said to Carlos that Canada may have just shown him who he always was. He sat with that, and then he said, you saw yourself. That exchange stays with me because I think it describes what community, real community, actually does. It holds up a mirror. And if we are lucky, what we see reflected back is generous enough to change what we give away. I am honoured to have been in that room. About the Host Katherine Dudtschak is the founder of Sincerely, host of The Sincerely Show, and author of Sincerely Katherine. She writes and speaks about leadership, service, and the interior life. Disclaimer This conversation is for reflection and perspective only and should not be relied on as therapy or professional advice. Please seek qualified support where needed before making any decisions based on the information you learn through this conversation. This content is also subject to our full Terms and Conditions, which you can review on our website at sincerelyinc.com.

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  Episode #18

  Melissa Bernstein: Turning the Chaos Within Into Light, One Life at a Time

  Sep 23, 20261h 32mS1

  Connect with Katherine Dudtschak Website: Sincerely Inc. LinkedIn: Katherine Dudtschak Instagram: @kdudtschak Connect with Melissa Bernstein Website: Melissa Bernstein LinkedIn: Melissa Bernstein Book: Lifelines Melissa Bernstein: Turning the Chaos Within Into Light, One Life at a Time There is a woman who has designed nearly ten thousand toys, built a preschool toy brand in the United States, and founded Lifelines to put sensory wellbeing tools into more hands. She coaches despondent strangers for free because she has learned, from the Talmud and experience, that to save one life is to save the world entire. That is Melissa Bernstein. Melissa describes growing up with a profound crisis of meaning and shaping herself around what she calls the three P's: perfectionism, pleasing, and performance. We trace the arc through her early twenties, when she and Doug left conventional careers, founded a toy company with their pooled savings, and discovered she could turn off the dark faucet and turn on the light. That led to her memoir, Lifelines, and the framework she calls the pie of meaning: building a life from many slices so no loss empties you. Katherine and Melissa find the same arc in each other and name it, two people meeting in the same truth. This conversation is for anyone who has wondered whether the quality that made them feel wrong might be the source of their best work. There are no promises of arrival, only an invitation to keep cultivating seeds and trust they will germinate in lives we may never see. Key Moments The three P's: how perfectionism leads to breakdown, pleasing to martyrdom, and performance to self-abandonment. Turning off the dark faucet: the moment Melissa understood she had a choice about what to create, and what it felt like to breathe. The pie of meaning, and why a life built on a single source of meaning cannot hold when that source changes. The childhood verse on seeds, written at eight and read aloud here: "keep on cultivating seeds, give them water, pull the weeds, then repeat it all again for we can't be certain when they will germinate and grow touching lives we'll never know." Quotes to Remember "I basically saw that I have a choice. I can choose to either create more darkness out of darkness... But now I actually metaphorically and figuratively turned off the dark faucet and I said, you know what? I'm just going to channel this very same unsettledness... into light." "when you save one life, you save the world entire... I have to do it one person at a time. And that that is more than enough." Reflection for Listeners What I keep sitting with is that verse Melissa wrote at eight about seeds. She didn't know she was writing her own instructions. The chaos she was trying to outrun would one day teach her to cultivate something in another person and let it go without needing to see where it lands. I've been thinking about those who planted seeds in me without knowing it, and what it means to give without needing to know the germination date. That is the gift Melissa handed me, and I am so glad she is in the world. About Host Katherine Dudtschak is the founder of Sincerely, host of The Sincerely Show, and author of Sincerely, Katherine . She writes and speaks about leadership, service, and inner life. Disclaimer This conversation is for reflection and perspective only and should not be relied on as therapy or professional advice. Please seek qualified support before making decisions based on this conversation. This content is also subject to our full Terms and Conditions, which you can review on our website at sincerelyinc.com.

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  Episode #18

  Eric Farewell: Becoming a Billionaire in Time, and Building a Life Around Love

  Sep 17, 20261h 8mS1

  Connect with Katherine Dudtschak Website: Sincerely Inc. LinkedIn: Katherine Dudtschak Instagram: @kdudtschak Connect with Eric Farewell Website: Eric Farewell LinkedIn: Eric Farewell Facebook: Eric Farewell Eric Farewell: Becoming a Billionaire in Time, and Building a Life Around Love A friend asked Eric Farewell two years ago if he could coach him. In what, Eric said. And the friend answered: you own four companies and you don't work. You have more time than anyone else I know. Eric replied without reaching for it. He calls himself a billionaire in time: a man who, having never had a childhood, is living one now, driving his kids four minutes to school, playing volleyball on the weekends, calling someone he loves every single time he gets in the car. He is a coach and mentor to founders, the builder of a community called Royals for men and women stepping into their highest selves, and a husband of seventeen years who will tell you plainly that presence is the only currency that has ever mattered to him. This conversation walks backward through the life that produced him. The seven-year-old who discovered that hard work made people call him remarkable, and who spent the next twenty-five years chasing that feeling through businesses, broken bones, and a marriage that very nearly ended. The convergence that came at thirty-two, when his body finally stopped him. And the years of somatic work, therapy, community, and radical honesty that brought him to the man sitting here now: loving, present, and genuinely grateful for all of it. In this conversation Eric talks about why grief must be witnessed in community, not carried alone. He talks about the one emotion men are given permission to feel, and the slow, beautiful work of learning to feel the rest. He shares what he looks for in a king or a queen, which has everything to do with where their boundaries are. And he talks about fear as a highway sign: the direction you are most afraid of is very likely the direction you are meant to go. Key Moments - Royals, and what actually distinguishes a king or queen: where their boundaries are, and what they have finally stopped performing in order to receive love. - The client who turned to him with tears in her eyes and said she thought she was last in her feminine when she was eight years old, and the moment Katherine names what Eric was doing: seeing through the layers to the soul, which Course in Miracles calls true empathy. Quotes to Remember "I'm a billionaire in time. I built my life. Like I didn't have a childhood. So I am living my childhood now." "My purpose on this planet is to help myself and others overcome fears to become present with who we truly are. All that fear is, is the antithesis of love." Reflection for Listeners What stayed with me after this conversation is the image of the seven-year-old who learned to be remarkable, and the forty-year-old who no longer needs to be. Eric said what he wants on his tombstone is the word "loved." Not what he built, sold, or survived. Just that he loved. Eric gave me one of the clearest answers I have ever received to the question of what it means to live sincerely human. A daily choosing, again and again, to feel the thing, say the thing, and let people in. About the Host Katherine Dudtschak is the founder of Sincerely, host of The Sincerely Show, and author of Sincerely, Katherine. She writes and speaks about leadership, service, and the interior life. Disclaimer This conversation is for reflection and perspective only and should not be relied on as therapy or professional advice. Please seek qualified support where needed before making any decisions based on the information you learn through this conversation. This content is also subject to our full Terms and Conditions, which you can review on our website at sincerelyinc.com.

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  Episode #17

  Jennifer Hill: The Spark of Light in Every Human We Meet

  Sep 10, 20261h 10mS1

  Jennifer Hill has spent her life learning to see the spark of light in every person she meets, and handing it back to them when they have forgotten it. She is the founder of the Jen Hill Tribe, a global community of entrepreneurs, thought leaders, and the founder of OptiMatch, an intelligent-matching platform built to connect people according to their motivational makeup, values, and numerological alignment. She shares 180 tools for self-regulation and inner peace, with anyone who wants them. This conversation walks backward through the chapters: a childhood spent contorting herself to earn love, an awakening at a personal development class outside LAX, and a decade of inner work that rewired the way she lived. It walks through the autism diagnosis that helped her understand her own brain, the founding of OptiMatch, and the vision two Decembers ago of a magical mirror in which she saw not her own reflection but everyone she had ever met reflected back to her. From that mirror came her purpose: to look for and listen for the spark of light in every human and reflect it back when they have forgotten. This episode is for anyone who has tried to earn love by becoming someone else, and is ready to find and reflect back, the spark of light that was always theirs. Key Moments The vision of the magical mirror: Jennifer recounts the Thursday morning session in Lisbon, two Decembers ago, where she was shown that her only purpose is to look for and listen for the spark of light in every human she meets and reflect it back to them when they have forgotten. The LAMP typology and the plus-two approach: Jennifer explains how understanding motivational type reveals why people cannot hear each other, and how rating your own energy after every interaction from plus two to minus two becomes a map of who belongs in your life. Jennifer describes what it means, in practice, to have transcended the fear of death, and shares the nightly spiritual accounting she and her husband observe: three questions asked before sleep, in good faith, every evening. A wish for humanity: Jennifer reads the words she wrote the day before her birthday, after postponing a flight to Israel as conflict broke out, a Kabbalistic teaching that any evil we witness in the world is a reflection of what lies unhealed in our hearts, and a wish that we each turn inward and make peace in the only place we truly have authority. Quotes to Remember "Your only purpose is to look for and listen for the spark of light in every human you meet and reflect it back to them when they've forgotten." "Until we can first repair that relationship with self, we're never going to be able to have deep intimacy with others." Reflection for Listeners What moved me most is the moment Jennifer said nobody had ever asked her about fear before. She has one of the most generous minds I have encountered in this room, and I watched her go genuinely still when I asked the question, and then answer it with a humility that undid me. She has transcended the fear of death, she told us, and she described it without drama. I am sitting with the question she asks herself every night: did I cause pain to anyone today, and how could I have lived the day better? That question, asked honestly and in good faith each evening, is its own kind of spiritual accounting. I am going to try it. About the Host Katherine Dudtschak is the founder of Sincerely, host of The Sincerely Show, and author of Sincerely, Katherine. She writes and speaks about leadership, service, and the interior life. Disclaimer This conversation is for reflection and perspective only and should not be relied on as therapy or professional advice. Please seek qualified support where needed before making any decisions based on the information you learn through this conversation. This content is also subject to our full Terms and Conditions, which you can review on our website at sincerelyinc.com.

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  Episode #16

  Chip Conley: From Return on Investment to the Ripple of Impact

  Sep 3, 20261h 13mS1

  Connect with Katherine Dudtschak Website: Sincerely Inc. LinkedIn: Katherine Dudtschak Instagram: @kdudtschak Connect with Chip Conley Website: Chip Conley LinkedIn: Chip Conley Instagram: Chip Conley Book : Chip Conley Chip Conley: From Return on Investment to the Ripple of Impact Chip Conley is the founder and executive chair of the Modern Elder Academy, the world's first midlife wisdom school, with two campuses and 9,000 alumni. He teaches people to find their footing in transitions, cultivate purpose, awaken wisdom, and reframe their relationship with aging and longevity. He has written eight books, and he now measures his life by a single phrase he says plainly and often: the ripple of impact. In this conversation, Chip and Katherine walk the full arc of his life, from his formation as the firstborn of two firstborn Stanford parents, programmed to achieve and perform, through his coming out at 22 on Independence Day in Greenwich Village, through the building of 52 boutique hotels over 24 years, and through the collapse in his late 40s that became the doorway to his life's next work. They talk about the Enneagram, the shadow side of the performer, and what it means to move from performative identity to essence. They talk about the midlife atrium, and about the Modern Elder, someone as curious as they are wise. This episode is for anyone standing at the threshold of their second adulthood, wondering whether their best work is behind them or ahead of them. Key Moments - The four pillars of the Modern Elder Academy: finding your footing in transitions, cultivating purpose, awakening wisdom, and reframing our relationship with aging and longevity. - The reframe that lands between them: Chip's phrase "the dark night of the ego" and the moment Katherine reflects it back, and both of them recognise it together. - The near-death vision of 40 small birds wearing slow-down slippers, and why birdsong became sacred to Chip from that day forward. - Katherine's own story of the 300 birds that gathered on the roof of Maison Millefleurs two days after a land-blessing ceremony, offered in return for his. - Moral beauty as the number one pathway to awe, and Chip's wish that the world would witness and be moral beauty for one another. Quotes to Remember "I've moved from the ROI of return on investment to the ROI of ripple of impact. And that's what gives me a sense of a high is to see the impact in small ways." "It's not about being youthful as you get older, it's about being useful." Reflection for Listeners What stayed with me, after Chip said "the dark night of the ego," was how precisely it names something I have tried to say in my own words so many times. The performance is what collapses. And in that collapse, if we can sit with it rather than escape it, we find the thing that was always there. Chip has lived this. He has built something beautiful from it. And I am so grateful he trusted us with all of it. About the Host Katherine Dudtschak is the founder of Sincerely, host of The Sincerely Show, and author of Sincerely, Katherine. She writes and speaks about leadership, service, and the interior life. Disclaimer This conversation is for reflection and perspective only and should not be relied on as therapy or professional advice. Please seek qualified support where needed before making any decisions based on the information you learn through this conversation. This content is also subject to our full Terms and Conditions, which you can review on our website at sincerelyinc.com.

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