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!

Hey friends, Chase here.

Emails. Deadlines. Chores. Repeat. Somewhere along the way, we traded play for productivity—and we’ve been tired ever since.

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 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 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.

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.

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!

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!

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.

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.

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.

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.

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.

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 author of We Need Your Art, a manifesto and practical guide for anyone seeking to live a more creative, authentic life.

In our conversation, we dive deep into what it means to choose yourself and stop waiting for permission to create. Amie talks about how she rewrote her story as a writer after being rejected by gatekeepers, turning her path around by embracing self-publishing and building a dedicated audience. We explore the tension between external validation and self-empowerment, why tiny steps are the secret to creative success, and the powerful mindset shift that allowed her to fully claim her identity as an artist.

• The moment Amie realized she didn’t need a publisher’s permission to call herself an author
• Why "tiny steps" are more powerful than bursts of inspiration in building a creative habit
• How relentless vulnerability helped Amie build an engaged online audience over 10 years
• The unexpected advice Amie received from established authors—and why she ignored it

Enjoy!

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.

The world conditions us to play it safe—to follow the map, not the compass. We’re told there’s a “right” way to live: go to school, get a stable job, and avoid risks. But what if that map is outdated? What if following someone else’s plan is the real danger?

🔥 The difference between a map and a compass—Why external advice can only take you so far. 🔥 Why playing it safe is the riskiest thing you can do—And how to reframe fear as a sign of growth. 🔥 How to take small, actionable steps toward your dreams—Without overthinking yourself into paralysis.

Fear will always be there. But so will your inner knowing. The key is learning to tell the difference—and having the courage to follow through.

Until next time, trust yourself. You already have the answers.

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 key. When you go all-in on one thing, you learn how to learn. You gain credibility, confidence, and connections that open doors to your next pursuit. Game recognizes game, and mastery attracts opportunity.

• The myth of "choosing one thing"—Success isn’t about picking a single path for life.
• Mastery as a launchpad—Why becoming great at one thing makes it easier to transition to the next.
• Start today—The best time to begin was 10 years ago. The second best time? Right now.

Until next time, keep pushing forward. Your dreams are worth it.

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.

Back in 2010, I co-founded CreativeLive with a simple but ambitious idea: to give the world access to free, world-class creative education. We started small, but over time, we grew to serve tens of millions of people and raised more than $60 million from top-tier investors like Richard Branson, Reid Hoffman, and Google Ventures.

At first, my unconventional background as a creator—not an MBA—was celebrated. I brought a personal brand and a community along for the ride, and it seemed like a competitive advantage. But eventually, the pressure to conform crept in. The same people who once admired my unique approach began questioning it.

What started as small adjustments in how I operated became a slow drift off course. It wasn’t dramatic at first—just a few degrees off. But after walking that path for long enough, I found myself far from where I wanted to be. The very thing I had built to inspire creativity felt stifling and uncreative.

And here’s the thing—this story isn’t unique to me. It happens to many of us. The artist who becomes a manager. The entrepreneur buried in spreadsheets. The corporate climber who wakes up one day and wonders how they got there.

If you’ve ever felt that way—or if you do in the future—this is for you.

1. Listen to Your Gut When something feels off for too long, it’s your gut telling you it’s time to move. Ignoring that voice comes with real consequences—stress, poor health, and a fog that clouds your creativity and joy.
2. Nothing Lasts Forever Even the most exciting roles can run their course. Dreams change, and that’s okay. Letting go of a title or identity that no longer serves you is hard, but it’s often necessary for growth.
3. Build Your Escape Pod Early Don’t wait for a crisis to figure out your next move. Start building skills, connections, and momentum now. When it’s time to make a change, you’ll be ready to transition on your terms—not out of desperation.

Change is inevitable. It’s uncomfortable, but it’s almost always a catalyst for something better. When you start hearing that little voice whispering about a new chapter, don’t ignore it. Trust it. Your future self will thank you.

Until next time, take care and keep pushing toward what feels true and right for you.

Enjoy!

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 fulfillment—one that balances time, social, mental, physical, and financial wealth.

We dive deep into why most people are measuring their lives all wrong, how to escape the trap of “later,” and why redefining your personal scoreboard is the key to happiness. Sahil also shares practical tools to reclaim your time, stop the busyness spiral, and align your daily actions with what actually matters. If you’ve ever felt stuck in the endless pursuit of “more,” this episode will change how you think about success forever.

• “Later is just another word for never.” Why waiting to enjoy life is the biggest mistake you can make.
• The energy calendar trick. A simple way to identify what drains and fuels you—so you can shift your schedule.
• The Red Queen effect. How endless busyness tricks you into thinking you’re making progress when you’re actually stuck.

Enjoy!