17. The Future of Work Is Human: How to Thrive in the Age of AI
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In a world spinning faster with every AI breakthrough, what does it actually mean to stay human? In this moving, insightful conversation, Hailey Krajewski is joined by Annemarie Penny—founder of Dreamore, advocate for liberated learning, and a true visionary in the future-of-work space—to unpack how we can thrive in an AI-powered future by returning to our roots: story, connection, creativity, and care.
From losing everything to rebuilding with deeper intention, Annemarie shares how the hardest chapters of her life reshaped not only her career but her entire outlook. This episode is part practical roadmap, part soul-stirring manifesto—and it’s a must-listen for anyone seeking meaning and momentum in uncertain times.
The Human Edge in an AI World
AI might be fast, but humans are deep. Annemarie challenges the panic-driven narratives around artificial intelligence and instead reframes it as a partner—not a replacement. She explains how skills like communication, empathy, critical thinking, and creativity are exactly what will set people apart in the next evolution of work. If you’ve ever doubted your place in a tech-forward world, this is the pep talk you didn’t know you needed.
The Double Phoenix Story: Loss, Rebirth, and Purpose
Annemarie’s story of losing two homes to wildfires isn’t just a headline—it’s a lesson in reinvention. She takes us through what it meant to burn it all down (literally) and still find purpose on the other side. Her story is both sobering and hopeful, reminding us that resilience isn’t about pushing through alone—it’s about drawing strength from community, and letting transformation guide your next step.
What Is Liberated Learning (and Why It Matters)?
Forget productivity hacks and grind culture. Annemarie introduces “liberated learning” as an entirely new framework—one rooted in curiosity, wellness, and the freedom to feel again. She describes how we’ve lost our sense of wonder and connection, and how re-humanizing our work starts with asking better questions, taking real breaks, and giving ourselves space to breathe. This section is rich with mindset shifts you’ll carry with you long after the episode ends.
Redefining Success (Hint: It’s Not About the Money)
For Annemarie, success has never been about a dollar figure or social media metrics. It’s about being able to pick up the phone, ask for help, and know someone will answer. It’s about leaving behind a legacy of kindness, not just accomplishments. In this powerful reflection, she invites all of us to rethink what we’re chasing—and why. If you’ve been feeling burnt out, disconnected, or caught in a comparison spiral, this reframe might be exactly what you need.
What You’ll Learn in This Episode
00:01:08 – Annemarie’s childhood roots and early self-taught education
00:06:09 – The isolating side of technology and how to reclaim connection
00:09:28 – Why AI is a tool for more human creativity—not a threat
00:14:50 – What liberated learning is and how it redefines growth
00:25:07 – The power of understanding your “why”
00:30:23 – How Annemarie reframed resilience after devastating loss
00:36:42 – A new definition of success rooted in relationships
Meet Annemarie Penny
Annemarie Penny is the CEO and founder of Dreamore, a women-, diversity-, and purpose-led firm reshaping the future of work through recruiting, career upskilling, and AI advisory. Known as a “double phoenix” for surviving two catastrophic wildfires, Annemarie has spent over three decades helping others rise, rebuild, and realign with what matters. She speaks globally on liberated learning, sustainable success, and the intersection of technology and humanity.
Connect on LinkedIn: Annemarie Penny
