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... read more ›

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... read more ›

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... read more ›

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... read more ›

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... read more ›

In this episode, Amie McNee shares why the world desperately needs your art—and how to overcome the inner obstacles that keep so many creatives from stepping into their full potential. Amie is an author, speaker, creative guide, and founder of the popular Instagram account @InspiredtoWrite. Known for her candid conversations about creativity and self-doubt, Amie has helped artists all over the world reclaim their creative power and build a sustainable, fulfilling practice. She’s also the... read more ›

Hey friends, Chase here. Ever had that gut feeling—the one whispering that you’re meant for something more? Maybe it nudged you toward a bold move, a creative dream, or a life change you couldn’t quite explain. But then, almost immediately, fear kicked in. “That’s risky.” “What if I fail?” “What will people think?” Here’s the truth: Your gut is rarely wrong. Fear, on the other hand, is loud, irrational, and loves to keep you small.... read more ›

Hey friends, Chase here. Ever notice how the world tries to box you in? It wants you to be one thing—safe, predictable, realistic. From a young age, we’re told to pick a career, stick with it, and not get too ambitious. But that’s just people projecting their own fears. I’m here to tell you: You don’t have to choose just one thing. You can build a multi-faceted life—just not all at once. Mastery is the... read more ›

Hey friends, Chase here. Today, I want to talk about something we all face at some point—the moment when what once felt like a dream becomes a trap. It’s a tough place to be, but if we can recognize it early, we can turn it into an opportunity for growth and reinvention. When Success Becomes Stifling Back in 2010, I co-founded CreativeLive with a simple but ambitious idea: to give the world access to free,... read more ›

In this episode, Sahil Bloom shares why chasing money alone won’t make you truly wealthy—and what actually will. Sahil is a writer, entrepreneur, and investor known for breaking down complex ideas into powerful, actionable insights. His debut book, The Five Types of Wealth: A Transformative Guide to Design Your Dream Life, challenges the belief that financial success is the only goal worth chasing. Instead, he reveals a new blueprint for building a life of true... read more ›