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The Work of You
This is a podcast about the leadership that matters most — the kind that starts from within.
Hosted by certified behavioral coach and Enneagram expert Jen Ostrich, The Work of You is for high-achieving humans ready to stop repeating patterns and start leading themselves differently.
Through insights from coaching, the Enneagram, and her own personal inner overhaul, Jen brings honesty, humor, and sharp emotional clarity to the table. With real talk, self-awareness tools, and a healthy dose of tough love, she helps you uncover what’s driving you, shift what’s no longer serving you, and ultimately do the work of you — one honest episode at a time.
This isn’t about fixing yourself. It’s about finally understanding yourself — so your choices, relationships, and leadership can actually align with who you truly are.
The Work of You
The Advice You Give vs. The Life You Live -- with CCO Jason Sperling [S2 Ep 18]
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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
