The Self-Led Life — A Conversation with Erin Gregory

Thank you Sarah Oehler, rhonda doruiter, Tom Janiak, Deanne Ames Original Junior-Senior and many others for tuning into my live video!How authenticity, courage, community, and the willingness to pivot can help us build a life that actually fits who we are.What happens when the life you are supposed to live no longer feels like the life you want?On this episode of The Positive Pen: Stories, Soul Work & Substack, I sat down with writer, entrepreneur, marketing strategist, and creator of The Self-Led Life, Erin Gregory, for a conversation about work, family, creativity, and what it really takes to build a life around your values.Erin’s journey didn’t begin with a perfect business plan. It began with motherhood.After her first daughter was born with several health challenges, Erin found that the traditional working world no longer fit her family’s needs. She began freelancing, moved through journalism and nonprofit marketing, and eventually created a business that gave her something she had been searching for: ownership of her days.That idea became the heart of the Self-Led Life.A self-led life isn’t about abandoning responsibility or suddenly quitting your job. It’s about asking whether the path you’re following still reflects your values, interests, abilities, family, and the person you’re becoming.Throughout our conversation, one phrase kept returning: the messy middle.Life rarely moves in a straight line. Erin and I talked about experimenting, failing, adjusting, and trying again. Whether you’re building a business, writing on Substack, raising children, changing careers, or discovering your creative voice, sometimes you have to begin before you completely understand where you’re going.We also explored the growing importance of authentic storytelling. In a world increasingly filled with AI-generated content, Erin believes people still want the human being behind the words—the experiences, imperfections, lessons, and perspectives that technology cannot manufacture.Perhaps the biggest message from our conversation was simple: you are never a finished product.We continue learning. We pivot. We discover new interests. We find new communities. And sometimes we realize that something that once served us no longer does.The goal isn’t perfection.It’s alignment.5 Lessons from Erin Gregory* Build around your values. Success means little if the life you’re creating doesn’t leave room for the people and experiences that matter.* Learn to pivot. A change in direction isn’t necessarily failure. Sometimes it means you’ve learned enough to recognize a better path.* Protect your authentic voice. Your experiences and perspective are what make your writing, business, and story uniquely yours.* Create a “third space.” Find something outside work and responsibility—gardening, running, writing, music, walking—where you can reconnect with yourself.* Community matters. Growth doesn’t have to happen alone. Collaboration, service, conversation, and helping others can become part of building a meaningful life.The Self-Led Life isn’t about having everything figured out.It’s about becoming willing to listen to yourself, do the hard work, and keep moving toward a life that feels genuinely your own.Thank you for your support. This work is reader-supported, and your presence here matters.About the AuthorJohn 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 Ciao Bella: 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.This work is protected under U.S. and international copyright law. No part of this publication may be reproduced, distributed, displayed, or transmitted in any form without prior written permission. Official publications are released only through verified accounts directly controlled by John V. Rinaldo.THE POSITIVE PEN is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit rinaldoj.substack.com/subscribe