What Would You Do If You Weren't Afraid? Season Three Wrap

What Would You Do If You Weren't Afraid? Season Three Wrap

We thought adulthood was the destination. It turns out it's only a stop along the way. After seven conversations about friendship, ambition, identity, and reinvention in midlife, I reflect on what I learned from the season and what those conversations revealed about my own next chapter. I'll bring the honesty. You bring the mixtape.

What We’ve Learned in the 25 Years Since College Graduation: a season 3 bonus feature

What does it actually look like to navigate life over the course of two decades after college? In this Season Three bonus feature of “I’m Here Too,” I asked my guests one question: What would you tell your younger self if you were the commencement speaker? What they shared wasn’t generic inspiration. It’s real talk about shifting paths, handling social pressure, and why taking action (“do the doing”) is more valuable than collecting credentials. If you’re navigating a career transition or looking for a fresh perspective on your professional journey, I hope these reflections help you move forward with confidence.

Honor Your DNA, a conversation with Leelila Strogov

In this episode, I talk with Leelila Strogov about ambition, stewardship, identity, and what responsibility looks like in midlife. Leelila is the Founder and CEO of AtomicMind, a global education consulting firm helping high-achieving students navigate some of the world’s most competitive institutions. But this conversation isn’t really about admissions. It’s about formation: how people learn who they are, what becomes possible for them, and whether ambition expands or constricts under pressure. We talk about honoring identity early, the difference between joyful ambition and imposed ambition, and why excellence should feel alive rather than extractive. We also explore technology as a tool for becoming more human, the discipline of protecting attention and trust, and what it means to use influence in ways that create possibility for others. Throughout the conversation is a deeper question: What responsibility do we have for the systems, stories, and environments shaping the next generation? Topics include leadership, parenting, institutional culture, technology, identity, ambition, stewardship, and generational responsibility. About Leelila Strogov Leelila Strogov is the Founder and CEO of AtomicMind, a global education consulting firm helping high-achieving students gain admission to the world’s most selective schools. AtomicMind is known for its exceptional success rates at Ivy League and IvyPlus institutions, driven by deep admissions intelligence and insight. Before launching AtomicMind, Leelila was an Emmy Award–winning investigative reporter and producer at Fox News in Los Angeles. She holds a B.S. from MIT and is recognized as a notable alumna. Blending analytical rigor with powerful storytelling, Leelila helps students stand out beyond grades and test scores—ultimately guiding students to craft applications that are strategic, authentic, and compelling.

I Wanted to Want It, a conversation with Rory Eakin

If you've ever chased a career path mostly because it was expected, and felt the gap between what you wanted and what you thought you were supposed to want, this one is for you. Rory Eakin spent a summer in a suit, in an office building, knowing it was wrong. He wanted to want it. He didn't. He said no to the job, went to Cape Town to teach math, and began a series of career deviations that he says got easier with each one. We talk about what it means to grow up with an inherited picture of what success is supposed to look like, and what happens when you start pulling away from it. About burnout and the self-understanding it can unlock. About identity and how hard it is to separate who you are from what you do. And about something that surprised him: a pull toward faith and community after years of describing himself as a confident atheist. About Rory Rory Eakin is a co-Founder and Director of CircleUp, a data analytics company founded to help entrepreneurs thrive. Prior to CircleUp, Rory served as Director of Investments at Humanity United, a private foundation. He started his career as a math teacher at the University of Cape Town. Rory received his MBA from Stanford, and a Master’s Degree in International Relations from the University of Cape Town. He grew up in Washington DC, and now lives in San Francisco with his wife and two children, where he enjoys hiking, board games, and Mario Kart.

Do the Doing, a conversation with Jon Zweifler

What would make you walk away from a Fortune 500 career to become an “old founder?” In this episode, I reconnect with my middle school buddy, Jon Zweifler. We talk about hitting a ceiling in your career and what happens when you realize there is no “next job” that will teach you something new. Jon shares his journey from the Fortune 500 to life as a tech founder who is building Reed AI from the ground up to turn real-world language into learnable moments for neurodivergent kids and how his personal journey inspired a platform helping children make more sense of the world around them.  We also get into parenting in a rapidly changing world, including the realization that some teenagers don’t see the point of having a driver’s license, what it’s like to raise a child without a clear timetable or milestones, and letting go of velocity when you are wired to optimize everything. Jon’s lightning round answers don’t disappoint. He manages to choose both options on more than one occasion, makes a bold claim about Carmen San Diego, and has a relatable insight as to why he didn’t need to watch The Real World. Join us as we talk about the long game of doing the work, even when there are no guarantees.