In this episode, I share how not playing it safe can be the most powerful decision you make—for your creativity, your career, and your life. I open up about scrapping a nearly finished book to write something bolder and truer, and why embracing discomfort is the path to fulfillment and impact.

This is a syndicate episode from the LinkedIn Speaker Series, where I sit down with Ashley Levy, Senior Director of Brand Marketing at LinkedIn, for a deep conversation about my latest book Never Play It Safe. We talk about trusting intuition, the myth of the linear career path, and the hidden cost of living by someone else’s script. If you’ve ever felt stuck in “shoulds” or worried that taking a leap is too risky, this one’s for you.

Some highlights we explore:

• The yellow sticky note that sparked the idea behind Never Play It Safe.
• Why playing it safe is actually the riskiest move you can make.
• The #1 shared trait of top performers from my 1,000+ podcast interviews.
• How attention, not time, is your most valuable creative asset.

Enjoy!

Hey friends, Chase here.

Ever feel like you're taking life a little too seriously?

Wake up. Work. Hustle. Repeat. Somewhere along the way, we stopped playing—and started grinding through our days like machines.

We were taught that being serious means being responsible. That fun is a distraction. That joy is something we earn.

But let’s be real—seriousness without joy just leads to burnout.

Play is where creativity begins. It’s what makes challenges fun and failure less scary. It helps you breathe, think, connect, and feel again.

You already know how to play, you’ve just forgotten. But it’s still there, waiting.

So try it. Loosen the grip. Smile more. Make life a little less rigid and a lot more yours.

Until next time, stay curious, and stay in the game.

In this episode, I share how putting your creative work into the world—no matter how small—can lead to massive, unexpected impact. I open up about my early days as a self-taught photographer, the pain and joy of learning through film, and how a backpacking trip with my wife turned into the start of an unconventional creative career.

This is a syndicate episode from the B&H Photography Podcast, where I sit down with Derek, Jill, and Mike to trace the arc of my journey—from building the Best Camera app and pioneering mobile photography, to founding CreativeLive and finding purpose through community. We talk about the cost of taking creative risks, the billion-dollar idea that got away, and the deeper why behind making and sharing your art. If you’ve ever doubted whether your creative voice matters, this episode is for you.

Some highlights we explore:

• • Why you only need 20 people to support your work and make a living.

• WThe emotional cost—and wisdom—of losing out on the Instagram moment.
• What “the best camera is the one that’s with you” really means.
• The key mindset shift: You’re not promoting, you’re connecting people to something they need.

Enjoy!

Hey friends, Chase here.

Ever get a gut feeling—but second-guess it because it doesn’t “make sense”?

You’re not alone. From a young age, we’re taught to value logic over instinct. To follow the rules. To ignore the quiet signals coming from within.

But science shows that your body—especially your gut—is constantly processing more than your conscious mind ever could. That inner knowing? It’s real. And it’s powerful.

In this post, we’ll talk about why so many of us lost touch with our intuition—and how to start tuning back in, one small decision at a time.

Your gut knows. It always has. The question is: are you listening?

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!