Stop Hiding Behind ‘Not Ready’ and Learn How to Begin Anyway
In this episode, Debbie Millman shares how to begin—even when you feel unready, unqualified, or full of doubt. Debbie is a designer, author, educator, and host of the pioneering podcast Design Matters. She's also the chair of the Masters in Branding program at the School of Visual Arts and editorial director at Print magazine. We talk about the creative risks Debbie took later in life, why fear and shame shaped her early path, and how she found fulfillment by making deeply personal work—without waiting for permission. From the grief of losing family to the joy of marrying at 57, this is a raw, powerful conversation about love, legacy, and the courage to start—even if you feel like a mess. Some highlights we explore: The myth of readiness – Why waiting to feel “good enough” keeps us stuck in place. Failures that shaped the path – From rejected applications to bad jobs, how struggle created space for clarity. Creating without permission – Why Debbie’s most meaningful work began when she stopped waiting to be chosen. Enjoy!
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55:17
What If Play Is Actually the Most Important Work You'll Ever Do?
Hey friends, Chase here. Ever feel like your life is all work and no you? Emails. Deadlines. Chores. Repeat. Somewhere along the way, we traded play for productivity—and we’ve been tired ever since. Why We Forget to Play From a young age, we’re taught that play comes after the work is done. But here’s the catch: the work never ends. So we keep pushing joy to the sidelines. Play Isn’t a Luxury—It’s a Lifeline Play isn’t just fun. It fuels creativity, lowers stress, and helps us feel alive. It’s not the opposite of work—it’s what makes work meaningful. What If Work Could Be Play? What if you danced while doing dishes? What if you made emails a game? What if you stopped calling it “work” and started calling it “life”? It’s not about changing what you do. It’s about changing how you see it. You Were Born to Play Play is your natural state. You don’t have to earn it—you just have to remember it. So go ahead. Laugh more. Move your body. Get weird. Play might just be the most important work you’ll ever do. Until next time, keep it playful.
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12:02
What If Your Hardest Climb Is Within?
In this episode, Melissa Arnot Reid shares what it really takes to climb—not just the highest peaks on Earth, but the deepest valleys within ourselves. Melissa is a world-renowned mountaineer, professional mountain guide, and the first American woman to summit Mount Everest without supplemental oxygen. She has spent years guiding others to the top of the world’s tallest mountains, but in this conversation, she opens up about an even greater challenge: facing the internal struggles that no summit can fix. We dive deep into the difference between achievement and self-worth, the pressure of proving yourself, and what happens when success doesn’t bring the validation you expect. Melissa shares the raw, untold side of her journey—the failures, the doubts, the painful past she had to confront, and the losses that forced her to reevaluate everything. She also discusses her new book, Enough, a raw and powerful memoir about what it really means to be enough, when success isn’t and the truth is harder than the summit. . Some highlights we explore: The fallacy of achievement – Why success doesn’t automatically bring happiness or contentment. "Am I good enough?" – The two questions that drove Melissa's biggest climbs—and biggest struggles. Lessons from the mountains – How extreme environments strip away who we pretend to be and reveal our true selves. The real hardest climb – The internal work of self-forgiveness, facing fear, and learning to let go of external validation. Enjoy!
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1:25:07
What’s Stopping You From Taking the Risk That Could Change Everything?
In this episode, Jenny Wood shares how to overcome fear and take bold action. Jenny spent 18 years rising from entry-level to executive at Google, where she founded one of the company’s largest career programs. Now, she’s the author of Wild Courage, a book that flips the script on success by reclaiming nine so-called “negative” traits—like being reckless, nosy, or shameless—and showing how they can fuel massive growth. We get into what it really takes to break through fear, bounce back from rejection, and build the kind of courage that moves your life and career forward. Jenny holds nothing back—sharing wins, stumbles, and the surprising moment she chased her now-husband off a subway car. Some highlights we explore: The email rejection that made her lose sleep—and what she did next Why separating “truths from tales” is a life-changing tool for fear How to reframe being “shameless” as a leadership superpower What it means to be obsessed... in the healthiest, most productive way Enjoy!
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57:20
Overwhelmed by Doubt? Here’s How to Quiet the Noise and Trust Yourself
Hey friends, Chase here. Ever had that gut feeling nudging you toward something bigger—only for fear to barge in with doubts? "What if I fail?" "What if this is the wrong move?" "What will people think?" I’ve been there. When I walked away from the U.S. Olympic Development soccer program to pursue photography, people told me I was crazy. And honestly? I wondered if they were right. But there was another voice—quieter, but just slightly louder than my fear. That whisper was enough to take the leap. Why Trusting Your Gut Feels Hard Our brains are wired for survival, not fulfillment. That’s why fear kicks in the second we consider something uncertain. But think about it—how often have you regretted following your intuition? Probably never. How to Know If You’re on the Right Path It’s simple: If it feels right in your gut, it probably is. If it feels wrong, it probably is. We spend so much energy ignoring what we know deep down. The moment you start listening, everything changes. Stop Following Someone Else’s Map Trying to live by someone else’s playbook has an expiration date. It might feel safe, but eventually, you’ll realize you’re off course. The good news? You don’t have to wait to start. Take the first step—messy, awkward, scared. Just start. Be 1% Braver Courage isn’t about eliminating fear; it’s about being just 1% braver than it. You will make mistakes, but none of it is wasted. Every misstep is just data that brings you closer to where you’re meant to be. So when your intuition whispers—listen. The most fulfilled people do. Until next time, trust yourself. You already have the answers.
Chase Jarvis is a visionary photographer, artist and entrepreneur. Cited as one of the most influential photographers of the past decade, he is the founder & CEO of CreativeLive. In this show, Chase and some of the world’s top creative entrepreneurs, artists, and celebrities share stories designed to help you gain actionable insights to recognize your passions and achieve your goals.
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