EPISODE · Jan 14, 2026 · 1H 3M
139. When someday becomes the ticket to what’s calling with Theresa Callahan
from Courageous Me · host Kim Payne
In this unexpectedly magical episode, we meet Theresa Callahan, an executive leadership coach, retreat leader, and woman whose life transformed the moment she stopped saying 'someday'.What begins as a conversation about courage unfolds into a rich, cinematic story of a single decision that changed everything: a one-way ticket to Tuscany booked from the back of a conference room, fuelled by a whisper Theresa could no longer ignore.From there, the episode weaves through themes of timing, self-trust, guilt, vulnerability, identity, love, leadership, motherhood…and what becomes possible when you finally listen to what’s been quietly calling for years.This is a feel-it episode.One that explores what happens just before we act, why so many of us delay what matters most, and how courage often shows up not as bravado, but as a quiet, trembling yes. If you’ve ever felt something tugging at you—a place, an idea, a version of yourself—and you talked yourself out of it because of age, responsibility, fear, or timing… this conversation is for you.Think of it as an invitation to notice the quiet ‘someday’ that you keep shelving.To question what it might cost to keep waiting.And to honestly wonder…What if someday is today? Key takeaways:o What happens when “someday” becomes impossible to ignore.o How a single, seemingly small decision can rewrite the next decades of your life.o Why guilt so often appears right before growth, especially if you’re used to putting everyone else first.o What solo time can reveal about who you are.o Why vulnerability is the true gateway to courage.o How being ready for love, purpose, or expansion starts with being open to receive it.o What shifts when you stop waiting to feel ready and start trusting what’s already stirring. Get in touch with Theresa:Website: Retreat to TuscanyInstagram: @retreat.to.tuscany Facebook: Retreat to Tuscany YouTube Channel: Retreat to Tuscany LinkedIn: Theresa Callahan Email inquiries for the Retreat Programs: [email protected] COURAGEOUS ME – THE BOOK Grab your copy of Courageous Me – The courage to turn someday into today. Where to find me: Website: Kim Payne LinkedIn: Kim Payne Instagram: @iamkimpayne Facebook: KimPayneBiz COURAGEOUS SHIFTWant to make the impact you know is possible without having everything figured out? Get access now to The Courageous Shift – a FREE 90 min audio mini-series to work out your next move. Want to get clear on your next steps in your business or career?Book a FREE 45 min Call to Action to help you get to the starting line.
What this episode covers
In this unexpectedly magical episode, we meet Theresa Callahan, an executive leadership coach, retreat leader, and woman whose life transformed the moment she stopped saying 'someday'.What begins as a conversation about courage unfolds into a rich, cinematic story of a single decision that changed everything: a one-way ticket to Tuscany booked from the back of a conference room, fuelled by a whisper Theresa could no longer ignore.From there, the episode weaves through themes of timing, self-trust, guilt, vulnerability, identity, love, leadership, motherhood…and what becomes possible when you finally listen to what’s been quietly calling for years.This is a feel-it episode.One that explores what happens just before we act, why so many of us delay what matters most, and how courage often shows up not as bravado, but as a quiet, trembling yes. If you’ve ever felt something tugging at you—a place, an idea, a version of yourself—and you talked yourself out of it because of age, responsibility, fear, or timing… this conversation is for you.Think of it as an invitation to notice the quiet ‘someday’ that you keep shelving.To question what it might cost to keep waiting.And to honestly wonder…What if someday is today? Key takeaways:o What happens when “someday” becomes impossible to ignore.o How a single, seemingly small decision can rewrite the next decades of your life.o Why guilt so often appears right before growth, especially if you’re used to putting everyone else first.o What solo time can reveal about who you are.o Why vulnerability is the true gateway to courage.o How being ready for love, purpose, or expansion starts with being open to receive it.o What shifts when you stop waiting to feel ready and start trusting what’s already stirring. Get in touch with Theresa:Website: Retreat to TuscanyInstagram: @retreat.to.tuscany Facebook: Retreat to Tuscany YouTube Channel: Retreat to Tuscany LinkedIn: Theresa Callahan Email inquiries for the Retreat Programs: [email protected] COURAGEOUS ME – THE BOOK Grab your copy of Courageous Me – The courage to turn someday into today. Where to find me: Website: Kim Payne LinkedIn: Kim Payne Instagram: @iamkimpayne Facebook: KimPayneBiz COURAGEOUS SHIFTWant to make the impact you know is possible without having everything figured out? Get access now to The Courageous Shift – a FREE 90 min audio mini-series to work out your next move. Want to get clear on your next steps in your business or career?Book a FREE 45 min Call to Action to help you get to the starting line.
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139. When someday becomes the ticket to what’s calling with Theresa Callahan
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