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One Year of Doing This Out Loud [S2 Ep 23]
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Click Here to Support: *If you're able to support this free independently produced podcast it would mean so much to me *
June 18th marks one full year of The Work of You, and Jen marks it the only way she knows how — with radical honesty. She takes you back to where the podcast began: a business that had slowed, time that needed a purpose, and a calling she couldn't ignore. What she didn't see coming was the perfect storm waiting on the other side of launch week — a psychological Enneagram retreat that surfaced repressed trauma, the onset of perimenopause, and months of feeling like a shell of herself. She shares how she navigated all of it, why she kept showing up, and what this year has clarified about what's coming next for The Work of You as a platform.
In this episode, we explore:
- Why the podcast started: How a season of financial uncertainty and slowed client work became the opening for something Jen had been called to build all along.
- The harder story: What really happened in the second half of 2025 — a psychological retreat that surfaced repressed trauma, perimenopause, and the weekly work of showing up anyway.
- What commitment actually looks like: The difference between staying accountable to numbers and staying accountable to yourself and the people you're showing up for.
- What's next: Jen's expanded vision for The Work of You as a full platform — including the Enneagram masterclass, self-guided coaching products, and what's coming in season three.
The Work of You - Reflective Prompts:
- Where in your life are you showing up even when it's hard, and have you given yourself credit for that?
- What are you currently doing more for external proof than for internal alignment, and what would it look like to shift that?
- Is there a version of the next chapter of your life that you're not letting yourself fully imagine yet — and what's in the way?
Next Week:
Have you had a favorite podcast interview, but wished you could ask the guest for clarification on something? Are you new to the enneagram and have questions on how to understand how it can work as a map? Are you in a leadership position and struggling to figure how to strengthen your relationship with your team? In next week's episode, Jen will be answering your questions on The Work of You Podcast. Submit any and all questions you may have related to the enneagram, leadership, personal growth, or The Work of You here!
Resources | Links:
Submit Your Question For My Q&A Episode Here
LAST CHANCE: Sign Up for The Work of You MasterClass on 6/25
Download this Free Resource: Discover Your Hidden Layer of Leadership
The Work of You on Substack
Instagram | The Work of You
Website | The Work of You
Instagram | Grow Collective
Website | Grow Collective
Support the show
View all episodes
By Jen OstrichSend some fan mail
Click Here to Support: *If you're able to support this free independently produced podcast it would mean so much to me *
June 18th marks one full year of The Work of You, and Jen marks it the only way she knows how — with radical honesty. She takes you back to where the podcast began: a business that had slowed, time that needed a purpose, and a calling she couldn't ignore. What she didn't see coming was the perfect storm waiting on the other side of launch week — a psychological Enneagram retreat that surfaced repressed trauma, the onset of perimenopause, and months of feeling like a shell of herself. She shares how she navigated all of it, why she kept showing up, and what this year has clarified about what's coming next for The Work of You as a platform.
In this episode, we explore:
- Why the podcast started: How a season of financial uncertainty and slowed client work became the opening for something Jen had been called to build all along.
- The harder story: What really happened in the second half of 2025 — a psychological retreat that surfaced repressed trauma, perimenopause, and the weekly work of showing up anyway.
- What commitment actually looks like: The difference between staying accountable to numbers and staying accountable to yourself and the people you're showing up for.
- What's next: Jen's expanded vision for The Work of You as a full platform — including the Enneagram masterclass, self-guided coaching products, and what's coming in season three.
The Work of You - Reflective Prompts:
- Where in your life are you showing up even when it's hard, and have you given yourself credit for that?
- What are you currently doing more for external proof than for internal alignment, and what would it look like to shift that?
- Is there a version of the next chapter of your life that you're not letting yourself fully imagine yet — and what's in the way?
Next Week:
Have you had a favorite podcast interview, but wished you could ask the guest for clarification on something? Are you new to the enneagram and have questions on how to understand how it can work as a map? Are you in a leadership position and struggling to figure how to strengthen your relationship with your team? In next week's episode, Jen will be answering your questions on The Work of You Podcast. Submit any and all questions you may have related to the enneagram, leadership, personal growth, or The Work of You here!
Resources | Links:
Submit Your Question For My Q&A Episode Here
LAST CHANCE: Sign Up for The Work of You MasterClass on 6/25
Download this Free Resource: Discover Your Hidden Layer of Leadership
The Work of You on Substack
Instagram | The Work of You
Website | The Work of You
Instagram | Grow Collective
Website | Grow Collective
Support the show