Conversations with Thomas

About Conversations with Thomas

Conversations With Thomas is a podcast where humor, heart, and a touch of sass collide. Hosted by Thomas Kevin Dolan, each episode explores raw, real topics like self-compassion, healing, and the delightful mess of being human. As the seventh of ten kids, Thomas didn’t always have a voice—now he’s sharing it with you, and trust us, you’ll want to hear this. Expect vulnerability, laughs, and thought-provoking questions that dive into subjects most people avoid (because, let's face it, some topics just need to be tackled). With a mix of wit and wisdom, Thomas takes you on a journey where you might cry, you might laugh, and you’ll definitely feel a little more connected to yourself and the world. New episodes drop every 2nd and 4th Monday. Tune in for a dose of honesty, heart, and just the right amount of quirky.

Publisher

Thomas Kevin Dolan

Category

education · society & culture

Language

en

Explicit

No

First episode

15 Sept 2023

Latest episode

12 Jan 2026

Latest episodes

47 episodes in the feed.

1. 

   12 Jan 2026

   The Pain of the Jump or the Pain of Regret

   The Pain of the Jump or the Pain of Regret Every life eventually asks the same question. Do you choose the pain of the jump, or the pain of regret? In this episode, Thomas reflects on the moment when staying begins to cost more than leaving. Through a personal story from his adolescence and inspired by the work of Victoria Erickson, he explores how shame, family legacy, and the body’s wisdom shape our turning points. This is not a conversation about dramatic leaps. It is about the quiet honesty that arrives before change. With grounded insight, subtle humor, and a simple reflective practice, this episode invites you to notice where familiarity may be replacing aliveness, and what it might mean to choose differently. If you are standing at the edge of a decision, this conversation offers a place to pause and listen.

2. 

   22 Dec 2025

   Break Your Shell

   Break Your Shell In this episode of Conversations with Thomas, Thomas shares a powerful story from his childhood about the moment he unknowingly absorbed the belief that money and happiness could not coexist. Decades later, that inherited message was still shaping his life in ways he never saw coming. Through therapy, coaching, and one very uncomfortable prosperity exercise, Thomas reveals how old stories become shells we grow inside and eventually outgrow. He unpacks why these shells form, why breaking them feels terrifying, and how we can loosen the patterns that keep us confined. With humor and heart, he offers a simple three-part practice for breaking any shell, whether it is rooted in scarcity, identity, worthiness, or fear. He also invites listeners to join HeartFULL Rebellion on Instagram for short, supportive videos that help you rise into the life you are becoming. If you are ready to shed an old story and breathe into something bigger, this episode is for you.

3. 

   8 Dec 2025

   The Courage to Be Stupid

   The Courage to Be Stupid We spend so much of life trying not to look foolish. We polish our words, perfect our image, and perform certainty — all to hide the places we feel unsure. But what if the moments we call stupid are actually moments of sacred openness? In this tender conversation, Thomas explores the lifelong pattern of masking vulnerability with knowing, and the healing that comes when we meet our own uncertainty with compassion instead of shame. Drawing on Gangaji’s invitation to “be willing to be stupid,” Jungian psychology, and modern neuroscience, he reveals how the courage to not know can free us from perfectionism and deepen our connection to self and others. Featuring insights from Esther Perel and rest activist Tricia Hersey, this episode invites listeners to reclaim curiosity, humility, and the quiet brilliance that lives inside imperfection. It includes a gentle, heart-based practice, The Three-Step Pause, for the moments you feel the urge to cover up instead of open up. A reminder that wisdom isn’t found in having all the answers. It begins in the willingness to learn out loud.

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

3 ratings

Spotify

5.0 / 5

5 ratings

Podcast Authority Score: 57 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

90

Social presence

0

YouTube

0

Engagement

60

Contact Conversations with Thomas

Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.