The Self-Led Life — A Conversation with Erin Gregory

On the next Stories, Soul Work & Substack, this coming Monday at 4:00 PM EST / 3:00 PM CST / 1:00 PM PST / EUROPE 9:00 PM GMT / 10:00 PM CET

I met Erin through Traci Edwards while helping behind the scenes with one of Traci’s live shows. At first, it was simply production—making sure everything ran smoothly. But as we talked, I quickly realized Erin was building something much bigger than a personal brand. She was building a life around purpose.

Erin is the voice behind The Self-Led Life, where she writes about the messy middle of careers, motherhood, identity, and creating meaningful work. Her writing isn’t about chasing success for success’s sake. It’s about asking better questions: Who am I? What matters? And how do I build a life that reflects both?

On this episode of Stories, Soul Work & Substack, we’ll explore the story behind Erin Gregory. What experiences shaped her into the person she is today? How did she move from helping others build brands to encouraging people to build lives they don’t need a vacation from? We’ll talk about the challenges of balancing career, family, and personal identity, and why she believes our greatest growth often happens in what she calls “the messy middle.”

We’ll also dive into the soul work behind her journey. The quiet work of letting go of expectations, rediscovering herself through motherhood, and learning that success means very little if it costs you your peace. Erin’s work reminds us that becoming who we are is rarely a straight path—it is shaped by uncertainty, resilience, and the courage to choose authenticity over approval.

Finally, we’ll talk about writing. Not as content or marketing, but as a way of making sense of life. Erin’s essays invite readers to slow down, reflect, and build a life that aligns with their values. How has writing helped her discover her voice? How has it made her a better leader, mother, and human being? And what can all of us learn from putting our own stories into words?

Join us for an honest conversation about purpose, identity, resilience, and the lifelong work of becoming your truest self.

Stories, Soul Work & Substack isn’t just about writing. It’s about the people behind the words, the soul work behind the journey, and the stories that remind us we’re never walking the path alone.

The Positive Pen

If you have a question, drop it in the comments below—or share it live during the show.

This coming Monday at 4:00 PM EST / 3:00 PM CST / 1:00 PM PST / EUROPE 9:00 PM GMT / 10:00 PM CET

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John Rinaldo writes Soul & Stories, a weekly publication centered on soul work, reflection, and the quiet process of becoming. He also hosts the live podcast Stories, Soul Work & Substack every Monday at 4 PM EST, where written ideas open into honest conversation.

He is currently working on The Hole: Forgotten in the Shadows, a documentary written and hosted by John Rinaldo and Hassan, telling the story of Italians who resisted and secretly helped smuggle Jews to safety during World War II.

Author’s Note: I have dyslexia and use assistive technologies, including AI-assisted editing, to improve grammar and readability. Every story reflects my lived experiences, voice, and final approval.

© 2026 John V. Rinaldo. All rights reserved.

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