The Advice You Give vs. The Life You Live -- with CCO Jason Sperling [S2 Ep 18]

What Happens When You Stop Doing Life in Order — with CPO Keesha Jean-Baptiste [S2 Ep 21]

Send some fan mail [https://www.buzzsprout.com/2503019/fan_mail/new] Click Here to Support [https://www.buzzsprout.com/2503019/support]: *If you're able to support this free independently produced podcast it would mean so much to me * In this episode, Jen is joined by Keesha Jean-Baptiste, a distinguished Chief People Officer specializing in HR transformation, to discuss the courage it takes to lead from your authentic essence when the environment around you is designed to diminish it. Keesha shares her powerful journey of navigating high-stakes leadership roles at companies like Hearst Magazines and Wieden + Kennedy, and the pivotal moment in Geneva where she chose her own integrity over a comfortable paycheck. They dive deep into the concept of "doing life in order" and what happens when the checklist of success—the degrees, the titles, the material gains—no longer satiates your soul. Keesha opens up about her personal rebirth at age 50, shifting from a performative stance to reclaiming her identity as a writer, speaker, and teacher. This conversation is especially for any high-achiever who feels the "quiet exhaustion" of leadership and is ready to trade external validation for internal peace and self-knowledge. In this episode, we explore: * Leadership as Energy: Why your impact on an organization is determined by the energy you transmit and how you manage your "inner code" under pressure. * The Mid-Life Rebirth: Moving past the "manual" of how life is supposed to look to discover your creative essence and rewrite your own story. The Work of You via Keesha Jean-Baptiste: 1. Do one thing this year that makes you uncomfortable, but in a structured way. How does pushing yourself in this way make you feel? When you start to face discomfort, you get so in touch with yourself by pushing to go deeper. 2. Take a moment and write down a decision that you made that you are proud of and a decision you made that you aren't? What can you learn from how you reacted/acted in each of these situations? 3. Ask someone close to you, "What do you see me doing when I'm at my best? What am I doing when I am my most authentic self? About the Guest:  Keesha Jean-Baptiste is a distinguished Chief People Officer specializing in HR transformation. With a nearly three-decades-long career, she has driven organizational and cultural change at renowned companies such as Hearst Magazines, Wieden + Kennedy, and Richemont International. Keesha holds a certification in compassionate leadership and is a coach for the Shift Positive 360® feedback method, further elevating the deep respect held among Chief People Officers. Her insights have been featured extensively in leading trade publications like ADWEEK and numerous podcasts, underscoring her influence and thought leadership on various HR topics. Resources | Links: Sign up for The Work of You MasterClass on 6/25 [https://go.theworkofyou.com/patterns] Download this Free Resource: Discover Your Hidden Layer of Leadership [https://go.theworkofyou.com/hiddenlayer] TWOY S1 E1 | Living in Alignment - The First Step in Leading You [https://www.buzzsprout.com/2503019/episodes/17243404] Keesha's LinkedIn [https://www.linkedin.com/in/keeshaj/] Keesha's Leadership Cert Program [https://thepeopleandculturemethod.com/center-for-compassionate-leadership-program/] The Work of You on Substack [https://substack.com/@jenostrich?r=271h03&utm_medium=ios&utm_source=profile&shareImageVariant=light] Instagram | The Work of You [https://www.instagram.com/theworkofyou] Website | The Work of You [https://www.theworkofyou.com/] Instagram | Grow Collectiv [https://www.instagram.com/the.grow.collective/]e Website | Grow Collective [https://growcollective.us/] Support the show [https://www.buzzsprout.com/2503019/support]

The Gift Hidden Inside Your Enneagram Type — with Diane Ring [S2 Ep 20]

Send some fan mail [https://www.buzzsprout.com/2503019/fan_mail/new] Click Here to Support [https://www.buzzsprout.com/2503019/support]: *If you're able to support this free independently produced podcast it would mean so much to me * In this milestone 50th episode, Jen is joined by her original Enneagram teacher and mentor, Diane Ring, for a full-circle conversation about the deep architecture of inner work. Diane brings three decades of experience coaching senior leaders to the discussion. They examine the Enneagram not just as a categorization tool, but as a "sense-making" GPS that can help accurately locate where someone is and provide a specific growth path to help move the "edges of a proverbial box". The conversation also dives into the "Core Gift" bridge, a framework that helps  distinguish between defensive personality strategies and the deeper "why" for being in the world. From real-world stories on shifting leader intensity to the introduction of EnneaEdge—an AI-supported Enneagram coaching experience designed for the "moments that matter"—this episode is an invitation to get out of your own echo chamber and engage with a professional mirror. In this episode, we explore: * The Enneagram as a Leadership GPS: Understanding the framework as a map that points to where you currently are and provides a specific growth path to help you break out of automatic identities.  * Shifting from Intensity to Grounded Presence: By recognizing an automatic pattern of "intensity," a leader can experiment with "downshifting" to find a calmer, more productive way of engaging with their team. * The Distinction Between Personality and Core Gift: While personality is a strategy system for self-protection, your core gift (such as attunement) is what you are uniquely called to give to the world. * EnneaEdge | AI-Supported Enneagram Coaching: To solve the problem of "fall off" after leadership workshops, Diane created an AI coach designed to help professionals apply Enneagram insights when they are most likely to succumb to autopilot default patterns. The Work of You via Diane Ring: 1. Find somebody with professional capabilities, a coach, mentor, or peer-support group, that can help you recognize and reflect on your patterns, motivations, and blind spots. The goal is to intentionally step outside your own echo chamber and build self-awareness through guided reflection. About the Guest:  Diane Ring is an executive coach who has been bringing the Enneagram into the real work of leadership for 30 years. Through her company, Ring Results, she helps senior leaders and teams understand the deeper patterns that shape how they communicate, make decisions, handle pressure, and relate to others. Diane is known for making the Enneagram practical, relevant, and deeply useful—helping leaders see not only why they do what they do, but also the core gifts they are here to bring forward. She serves on the faculty of Integrative Enneagram Solutions and has presented several times at global Enneagram conferences. Diane is also the creator of EnneaEdge™, an AI-supported Enneagram coaching experience designed to help leaders apply insight in the moments that matter. Resources | Links: Download this Free Resource: Discover Your Hidden Layer of Leadership [https://go.theworkofyou.com/hiddenlayer] Get Your Enneagram Report Here [https://www.theworkofyou.com/enneagram] Diane's Company | Ring Results [https://www.ringresults.com/] LinkedIn | Diane Ring [https://www.linkedin.com/in/dianering] The Work of You on Substack [https://substack.com/@jenostrich?r=271h03&utm_medium=ios&utm_source=profile&shareImageVariant=light] Instagram | The Work of You [https://www.instagram.com/theworkofyou] Website | The Work of You [https://www.theworkofyou.com/] Instagram | Grow Collectiv [https://www.instagram.com/the.grow.collective/]e Website | Grow Collective [https://growcollective.us/] Support the show [https://www.buzzsprout.com/2503019/support]

Permission to Own What You Want [S2 Ep19]

Send some fan mail [https://www.buzzsprout.com/2503019/fan_mail/new] Click Here to Support [https://www.buzzsprout.com/2503019/support]: **If you're able and willing to support this free independently produced podcast it would mean so much to me * In this episode, Jen shares a vulnerable personal moment of "standing in her personal power" by handing her book proposal to a New York Times bestselling author—an act that required overcoming her own inner code of playing it small. She explores the "cost of silence" and why declaring a vision is not a jinx, but rather a way to recruit the support and accountability needed to turn ideas into realized reality. Whether you are a high-achiever hiding a dream until success is guaranteed or a perfectionist waiting for the right moment, this conversation is for you. Jen breaks down how different Enneagram types uniquely self-sabotage by keeping their goals invisible and offers practical prompts to help you name your "meaty goals" loudly and proudly. This episode is for any leader ready to stop "building in the background" and start inviting others to walk alongside them in the work of you. In this episode, we explore: * Declaring vs. Jinxing: Declaring a goal doesn't jinx it; it recruits others onto your "sidelines" to act as cheerleaders, coaches, or accountability buddies. * The Power of "Naming It": Growth comes to those who learn to say the thing out loud—whether it is an observation, a vision, or a dream—even when it feels risky. * Listening to the "Tiny Voice": Identifying the instinctual visions that have become difficult to ignore and moving them from your head onto paper. The Work of You - Reflective Prompts:  I would encourage you to sit down for 30 minutes and journal with a couple of these prompts, feel free to come back to them and reflect as needed. 1. What's one thing you've been working on quietly in the background, maybe just in your head, maybe you haven't even written it down yet? What would change if you said it out loud this week? 2. What is something that makes you a little uncomfortable to even think about, but also feels so instinctually on point that it's really become difficult to ignore?  3. Once you've identified a few examples, just name it. You could give it a code name or just write it out in terms of a goal. See what happens once you allowed yourself to lean into this vision or allowed yourself to actually want this for yourself. Resources | Links: Download this Free Resource: Discover Your Hidden Layer of Leadership [https://go.theworkofyou.com/hiddenlayer] Sign Up for The Work of You MasterClass on 5/27 [https://go.theworkofyou.com/patterns] Dogs, Boys, and Other Things I've Cried About by Isabel Klee [https://www.amazon.com/Dogs-Other-Things-Cried-About/dp/0063451077] The Work of You on Substack [https://substack.com/@jenostrich?r=271h03&utm_medium=ios&utm_source=profile&shareImageVariant=light] Instagram | The Work of You [https://www.instagram.com/theworkofyou] Website | The Work of You [https://www.theworkofyou.com/] Instagram | Grow Collectiv [https://www.instagram.com/the.grow.collective/]e Website | Grow Collective [https://growcollective.us/] Support the show [https://www.buzzsprout.com/2503019/support]

The Advice You Give vs. The Life You Live -- with CCO Jason Sperling [S2 Ep 18]

Send some fan mail [https://www.buzzsprout.com/2503019/fan_mail/new] Click Here to Support [https://www.buzzsprout.com/2503019/support]: *If you're able to support this free independently produced podcast it would mean so much to me * In this episode, Jen is joined by Jason Sperling, Chief Creative Officer at INNOCEAN and author of Creative Directions, to discuss the messy, often terrifying transition from being a "man-child" creative to a responsible leader. They explore the unique architecture of those wired for commercial creativity: the outliers who find themselves suddenly responsible for the careers of others while navigating their own imposter syndrome. Jason shares some of his most vulnerable "growth moments," from a high-stakes DEI mistake at Meta Reality Labs to the "periodic peril" of launching the iPad under Steve Jobs. We dive deep into why "candor is kindness" and how the hardest part of leadership is often managing the unrealistic expectations we set for ourselves versus the realistic ones we must set for our teams.  In this episode, we explore: * The Transition from Talent to Leader: Why being great at your craft doesn't automatically make you great at managing people, and the emotional maturity required to bridge that gap. * Managing Self-Expectations: Learning to separate the perfectionism you demand of yourself from the standards required to lead a healthy, functioning team. The Work of You via Jason Sperling: *  "Self-reflection helps build self awareness." * "Continue to push and find areas where you can improve. It's very easy to fall into the things that you're talented in and that come naturally to you, but push on those areas where you feel you're deficient with the hope that when you do it long enough it does start to come natural or feel less uncomfortable." About the Guest: Jason Sperling joined INNOCEAN in February 2023 as the Chief Creative Officer, and has helped transform the global agency’s creative vision and leveled up the work. And for the first time in the agency's history they've been included on Ad Age's A-List. Prior to this he served as Global Executive Creative Director for Meta Reality Labs, overseeing the global marketing for VR, AR and Metaverse. During his career he’s developed iconic work for brands like Apple, Honda, TikTok, Amazon, Disney Pixar and UNICEF Worldwide. His work has put him on several industry best lists, including Adweek’s Top 30 Creative Directors and Campaign’s 40 over 40 Best Digital Creatives. And his commitment to culture recently landed him on AdWeek's list of Architects of Culture list. Jason’s most recent book, Creative Directions: Making the Move from Talent to Leader (HarperCollins Leadership, 2021) provides creative people with the tools to become effective creative leaders.  Resources | Links: Jason's Book | Creative Directions [https://www.amazon.com/Creative-Directions-Mastering-Transition-Talent/dp/1400222893] Jason's LinkedIn [https://www.linkedin.com/in/mrjasonsperling/] The Work of You Masterclass [https://go.theworkofyou.com/patterns] Free Download: Discover Your Hidden Layer of Leadership [https://go.theworkofyou.com/hiddenlayer] The Work of You on Substack [https://substack.com/@jenostrich?r=271h03&utm_medium=ios&utm_source=profile&shareImageVariant=light] Instagram | The Work of You [https://www.instagram.com/theworkofyou] Website | The Work of You [https://www.theworkofyou.com/] Website | Grow Collective [https://growcollective.us/] Support the show [https://www.buzzsprout.com/2503019/support]

Your Hidden Layers — What I Learned About Mine [S2 Ep17]

Send some fan mail [https://www.buzzsprout.com/2503019/fan_mail/new] Click Here to Support [https://www.buzzsprout.com/2503019/support]: **If you're able and willing to support this free independently produced podcast it would mean so much to me * Leadership training often fails because it stays above the waterline, coaching the 10–20% of ourselves that is visible while ignoring the vast architecture running beneath. In this solo episode, Jen explores the Hidden Layer: the subconscious "inner code" of beliefs and core fears that act as the true drivers for how you show up. Using the human iceberg model, she shares why behaviors are usually just symptoms and how sustainable change requires working with the layers sitting deep below the surface. Jen also share a vulnerable letter to her 30-something self—a version of her who used "giving" as a strategy to feel lovable while remaining blind to the patterns that were exhausting her. By mapping Jen's own journey as an Enneagram 2, she shows  how naming your hidden layers creates the distance needed to move from automatic ego reactions back to your authentic essence. In this episode, we explore: * The Human Iceberg: Why behaviors are symptoms of the subconscious architecture beneath the waterline. * The Hidden Layer: A walkthrough of defense mechanisms, beliefs, motivations, and core fears. * Transactional vs. Transformational Change: Why working only at the behavior level leads to temporary shifts. * Ego vs. Essence: Shifting from automatic survival patterns to intentional self-leadership. The Work of You - Reflective Prompts:  1. Think of a challenging behavior you've been trying to change—if that behavior is just a symptom, what belief is sitting at the bottom of your iceberg driving it? 2. Where is your "inner code" currently running the show without your awareness? 3. If you could name the core fear your ego is trying to protect today, how would that awareness change your next move? Resources | Links: The Work of You Masterclass [https://go.theworkofyou.com/patterns] Free Download: Discover Your Hidden Layer of Leadership [https://go.theworkofyou.com/hiddenlayer] Get Your Enneagram Report Here [https://www.theworkofyou.com/enneagram] The Work of You on Substack [https://substack.com/@jenostrich?r=271h03&utm_medium=ios&utm_source=profile&shareImageVariant=light] Instagram | The Work of You [https://www.instagram.com/theworkofyou] Website | The Work of You [https://www.theworkofyou.com/] Instagram | Grow Collectiv [https://www.instagram.com/the.grow.collective/]e Website | Grow Collective [https://growcollective.us/] Support the show [https://www.buzzsprout.com/2503019/support]