The leadership conversation nobody else is having.
Most leadership content tells you what to do.
This show asks you to look at who’s doing it.
Every week Jen Ostrich goes beneath the surface of leadership — into the patterns, the blind spots, the unconscious strategies, and the stories leaders tell themselves — to explore what it actually takes to lead well from the inside out.
With honesty, humor, and a sharp dose of emotional clarity, each episode brings you insights from coaching, the Enneagram, and lived experience that you can apply immediately to how you lead, how you show up, and how you understand yourself.
This isn’t about fixing yourself. It’s about finally understanding yourself.
New episodes drop every Wednesday at 6am EST.
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All episodes below
Bonus: Reflections on the Inner Work Journey
How's it going for you -- doing the work of you?
As we approach a milestone of 10 episodes coming up this week; I felt called to drop an "off the cuff" bonus episode. In it I share what came up for me after hearing Oprah interview the co-founder of the Hoffman Process, Raz Ingrasci. And this notion of substituting vibrancy and happiness with success. I also check in and reflect on where I'm at in my own inner work journey since attending Hoffman in 2016 and I nudge you to check in by asking -- how's it going for you since you started listening? This is hard work and it's important to me that we all feel and trust that we're in this together.
Ep 9: What if the Enneagram Had a Tail? Learn the 9 Types as Dog Breeds
Learning the 9 Enneagram types through the most soulful, intuitive beings — dogs.
Today’s episode is all about connecting with the Enneagram in a fresh and engaging way that sticks while helping you do the work of you by understanding yourself on a deeper level. Jen taps into the best qualities of each Enneagram type by bringing to light some of the most soulful, intuitive and lovable creatures: DOGS. As a passionate dog lover, Jen shares two breeds per type to cover the different expressions of each type’s energy. Be sure to listen closely for some special dog shoutouts (and check the @theworkofyou Instagram page for dog pics)! Remember – not all types look the same – when you add your dominant instinct into the mix it can look different. This is covered briefly in EP 5, and there will be a future episode that dives into the 3 instincts further and the 27 subtypes of the Enneagram. For now in this episode, listen for what overarching pieces feel deeply resonate for you -- which dog breed are you?
Ep 8: Reimagining Feedback: A New Way to Grow
What if feedback felt inspiring and inviting vs something you dread or want to avoid?
Feedback doesn’t have to feel like criticism. In this episode, Jen explores a new way to think about feedback using the Shift Positive® method — a strengths-based, solution-focused approach she co-created that's centered around creating a supportive feedback experience. Despite the best of intentions most of the feedback methods out there have not been designed with the brain in mind. We'll get into the neuroscience and why it makes feedback feel so hard. Then we'll do into 3 immediate shifts you can make in you approach to gathering and giving feedback to make it far more effective and energizing.
Ep 7: The Truth About Change -A Birthday Tribute to the People Who Helped Me Grow
This episode drops on my 49th birthday so what better than time than now to pause and reflect on some special people who have helped my growth journey. True growth happens in connection — through allies, mirrors, feedback, and belonging. This episode is a personal celebration and a coaching truth: we do not transform alone. If you're a dog lover - be sure to listen to the very end when end for Koko’s special birthday cameo.
Ep 6: Why Your Strengths Matter More Than Weaknesses
What if the key to your growth isn't fixing what you've been told is a weakness or an area that you need to improve; instead, it's about doubling down on your strengths?
Today's focus is on strengths and why they matter more than your weaknesses. Strengths are a foundation for self-leadership and growth. This is an invitation for you to, instead of obsessing over where you need to improve or what might be some of your weaknesses, to actually think even more than you ever have before about your strengths. The the work of you is about leading from your core, your authentic core, and your strengths are a huge part of that.
Ep 5: Why the Enneagram is a Leadership Superpower
The Enneagram is powerful, but also widely under leveraged and often misunderstood. Let's get into why it's your leadership superpower!
This episode is an introduction to clarify what is the Enneagram (and all of its layers), what it's not AND how to use it in practice. ENNEA (greek word for nine) and GRAM (greek word for diagram) makes the 9 point symbol or diagram that is the Enneagram model. This episode is to ground you in the ways you can use the Enneagram in people and team development and all the aspects that help you to understand yourself. In future episodes we'll dive into the nine types in addition to going deeper in each of the layers of data that are available to do the work of you.
Ep 4: Breaking Free from the Patterns That Hold You Back
What if your patterns — even the ones that trip you up — are actually trying to protect you?
Let's dive into personality patterns -- what they are, why they are essential to understand about ourselves and how to learn how to manage them. I share the single most profound developmental experience I've been through, the Hoffman Process (link below) where I came to terms with my patterns and learned how to manage them. We'll dive into how to identify yours and tools to learn how to recognize when and where they are showing up. Always remember -- you are NOT your patterns; they are a part of you...but not all of you.
Ep 3: The Myth of Fixing Yourself
What if growth doesn’t start with fixing, but instead with understanding ourselves?
In this episode I reflect on how as a society it seems we're so focused on needing to fix ourselves. Or even thinking we are broken in some way aka in need of fixing. We look at the role fixed and growth mindset can play in this (and my own experience of falling off a bike at a young impressionable age) as well as negativity bias and other concepts brought to light via Positive Psychology. Ultimately I offer an invitation to rebrand the need or desire to fix yourself, and instead work to better understand yourself. This is far more valuable!
Ep 2: The Leadership Gap No One Talks About
What if the part of leadership that needs the most attention isn’t on your resume?
In this episode I talk about how professional development and personal development are not the same and it's critical to not assume one can accomplish the other. If/when professional development is a priority within an organization, aka there is budget, rarely does it focus on personal development – where the real work lies and where there is an ever greater impact for the leader and everyone around them. Professional development teaches strategy and execution, but not emotional regulation or inner clarity. Both are very important yet professional development most certainly cannot replace personal development.
Ep 1: Living in Alignment — The First Step to Leading You
Why are you the hardest person you'll ever lead?
In this episode we reflect on how we move through life often being out of alignment with our most authentic self. This makes leading you much more complicated. I share a simple framework I created that challenges you to see where you are living in full alignment with who you are, and where are you not? I share my crossroads moment and invite you to consider each and every aspect of your world and how it could be more aligned to you (vs the person you been hustling to be, feeling you should be, or trying to be to make others happy). This is when you're leading you.
