Fearless Creative Leadership

Charles Day
  • 4.9 (82)
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We talk to leaders of the world's most disruptive companies about how they are jumping into the fire, crossing the chasm and blowing up the status quo. Leaders who've mastered the art of turning the impossible into the profitable.

  1. Ep 288: Cat van der Werff of Canva - "The Freedom Leader"

    2D AGO

    Ep 288: Cat van der Werff of Canva - "The Freedom Leader"

    How much freedom do you give your people? In this episode of Fearless Creative Leadership, Charles Day speaks with Cat van der Werff, Executive Creative Director of Canva, about the paradox at the heart of modern leadership: setting clear standards while letting go of control. As Canva has grown from hundreds to thousands of employees, Cat's own evolution as a leader has mirrored that scale. A self-described perfectionist, she discovered that perfection can quietly suffocate creativity — and that excellence is only possible when leaders trust others to find their own way. They explore creativity as a human birthright, why empowering everyone to design elevates professional designers, how AI can expand imagination rather than replace it, and what it takes to build cultures rooted in trust, playfulness, and shared ownership. This is a thoughtful, deeply human conversation about freedom, responsibility, and what it really means to unlock creative potential at scale. 00:00 — Opening Question: Freedom & Leadership How much autonomy leaders truly give their people. 01:20 — Introducing Cat van der Werff & Canva Creativity, scale, and empowering the world to design. 03:10 — Creativity at an Early Age Drawing, observation, and imagination as instinct. 06:45 — Craft, Photography, and Self-Care Why leaders need creative practices of their own. 08:40 — Why Business, Not Fine Art Problem-solving, briefs, and applied creativity. 10:00 — Becoming a Leader From individual contributor to leading through others. 11:35 — Creativity as an Organizational Act Why org design and team structure are creative work. 14:30 — Vision, Scale, and Big Goals Operating from the future to guide growth. 17:10 — Creativity, Belonging, and Self-Actualization Why empowering creativity meets a fundamental human need. 21:35 — If Everyone Can Design, What's the Designer's Role? How democratization elevates strategic creativity. 24:15 — Building Empowered Cultures Small teams, trust, and shipping fast. 26:25 — Letting Go of Perfection Why perfectionism is selfish — and excellence is shared. 31:55 — Trust, Brand Integrity, and Boundaries How leaders intervene without controlling. 35:05 — Casting the Right People Playfulness, humility, and continual learning. 37:00 — AI, Imagination, and Confidence Why technology can't replace human creativity. 42:15 — Parenting, Creativity, and Presence Teaching creativity through doing, not instruction. 45:30 — Leading at Scale The tension between outward visibility and internal connection. 50:35 — Advice to Her 20-Year-Old Self Fun, creativity, and releasing pressure. 52:20 — Hope for the Future The coming "imagination era."

    54 min
  2. Ep 287: Aaron Starkman of Rethink - "The Buttoned Down Leader"

    FEB 6

    Ep 287: Aaron Starkman of Rethink - "The Buttoned Down Leader"

    What kind of box are you building for your people? In this episode of Fearless Creative Leadership, Charles Day sits down with Aaron Starkman, Chief Creative Officer of Rethink and one of Adweek's 100 Most Creative People in the World. But this is not a conversation about freedom from structure — it's about why the most creative environments are built on the most thoughtful processes. Aaron shares how creativity first became his refuge as a child, how anxiety and leadership collided early in his career, and why embracing structure, clarity, and guardrails is the fastest way to unlock originality. He explains how Rethink's disciplined systems remove friction, protect ideas, and give creative people the oxygen they need to do their best work. This is a deeply human conversation about creativity, leadership, vulnerability, and designing environments where people — and ideas — can truly thrive. 00:00 — Opening: The Box You're Building Creativity, structure, and the environments leaders create. 01:00 — Introducing Aaron Starkman Why discipline, not chaos, fuels great creative companies. 03:20 — Creativity as a Safe Place Childhood, adversity, and discovering creativity as refuge. 07:00 — Validation, Anxiety, and Self-Worth How early experiences shape creative drive. 13:10 — Do Creatives Need External Validation? Art, commerce, and the difference between personal and commercial creativity. 18:00 — Becoming a Leader (Reluctantly) Social anxiety, false confidence, and finding an authentic leadership style. 25:50 — Designing the Rethink Environment Why structure "murders hurdles" and protects ideas. 30:00 — CRAFTS and Creative Guardrails Process as a catalyst, not a constraint. 38:40 — Talent, Culture, and Casting Why not everyone thrives in every creative environment. 42:30 — Advice to His 25-Year-Old Self Mental health, therapy, and learning to smell the roses. 47:15 — What's Next Curiosity, relationships, and redefining success beyond titles.

    53 min
  3. Ep 286: Andrés Ordóñez of McCann - "The Impactful Leader"

    12/12/2025

    Ep 286: Andrés Ordóñez of McCann - "The Impactful Leader"

    What impact are you having? In this episode of Fearless Creative Leadership, Charles Day speaks with Andrés Ordóñez, newly appointed Global Chief Creative Officer of McCann. When this conversation was recorded, Andrés didn't yet know his future — which makes this a rare portrait of a leader reflecting not on a title, but on who he is. Across a deeply personal conversation, Andrés describes the forces that shaped him: a childhood surrounded by creativity, a mother whose illness forged his sense of responsibility, and a career built on connection, curiosity, and generosity. He talks about leading with humanity, navigating the upheaval of AI, and the responsibility that comes with carrying the torch for thousands of people across a global organization. This is a conversation about impact — the kind you have on work, on people, and on the world. 00:00 — Opening: The Impactful Leader Charles introduces the theme: leadership as responsibility and impact. 03:00 — Andrés's Creative Origin Story Family, Colombia, motorcycles, and the early spark of advertising. 07:00 — Childhood, Parents, and Identity Emotional bonds, choosing to live with his mother, and lessons that shaped him. 12:00 — Becoming a Caregiver at 18 Responsibility, work ethic, and how caring for his mother changed him. 16:30 — Defining Leadership & Creativity Connecting people, solving problems, the spark of creativity. 22:00 — AI: Partner, Tool, and Test of Humanity The future of creativity, trust, and why machines can't feel goosebumps. 28:30 — The Business Model of the Future Time, efficiency, and rethinking how creative value is measured. 32:00 — Casting People & Building Culture Human connection, belonging, and why team energy matters more than résumés. 37:45 — Responsibility Without Control Leading collaboratively while carrying the weight of outcomes. 41:00 — The "And" Philosophy Why mixing magic and logic changes everything. 46:00 — Change, Uncertainty, and the IPG–Omnicom Merger How Andrés holds ambiguity and stays grounded. 50:00 — Fear, Evolution, and Personal Growth The dangers of fear, staying curious, and the need to evolve. 54:00 — Defining Success Helping others realize their dreams — and the power of not putting yourself first. 59:00 — Closing Reflections Legacy, hope, and carrying the torch for ot

    50 min
  4. Ep 285: Ace of Hearts - "The Alive Leaders"

    12/05/2025

    Ep 285: Ace of Hearts - "The Alive Leaders"

    How alive do you feel as a leader? In this episode of Fearless Creative Leadership, Charles Day sits down in London with the newly announced founders of Ace of Hearts — Rick Brim, Martin Beverly, and Polly McMorrow — for their first recorded conversation as partners. Over the past seven months, Charles has interviewed them individually while they prepared to build something of their own. Now, you'll hear what happens when belief meets reality. They discuss why they started the company, the chemistry that binds them, what they're learning about themselves, and how creativity must be valued differently if the industry is going to survive disruption — including AI. This is a rare, unpolished look at the emotional and practical journey of starting a business. It reveals how fun, fear, optimism, and ambition shape founding teams — and why starting a company may be the most alive a leader ever feels. 00:00 — Opening: How alive do you feel? Welcome, framing creativity as the only scalable advantage. 01:03 — Introducing Ace of Hearts A glimpse into aliveness, excitement, and possibility. 03:30 — Why start a company now? Martin on timing, intuition, and the pull of founding. 07:30 — What founders want to find out about themselves Uncertainty, relearning, and stepping into the unknown. 12:00 — What kind of business are they building? Pride, impact, fun, culture — and why it matters. 15:00 — How thinking has evolved over the past months Confidence, experimentation, redefining where they play. 19:30 — The future of creativity and value exchange Human creativity, AI, commercial models, risk-taking. 24:00 — From clients to partners Trust, alignment, value creation — and saying no. 31:30 — What they're truly good at Finding the soul of brands — and owning it. 45:00 — The name revealed: Ace of Hearts Meaning, emotion, optimism, and brand potential. 52:00 — Closing and next steps Looking ahead — meeting at Cannes and bonus episodes.

    1h 9m
  5. Patricia Corsi of Kimberly-Clark - "The 'Make Mistakes' Leader"

    11/14/2025

    Patricia Corsi of Kimberly-Clark - "The 'Make Mistakes' Leader"

    How do you react when people make mistakes? Patricia Corsi is the Chief Growth Officer of Kimberly-Clark. Patricia has been named one of the Top 50 Most Influential CMOs of the World by Forbes in 2024 and 2025. She has very clear beliefs about how to unlock creativity and innovation in her business, and the kind of leadership that requires. Creativity and innovation are unpredictable. They demand uncertainty and depend on failure. Failure is how we learn and without it, creativity dies. Modern society isn't good on failure. We look for likes and follows and success, defined across as many metrics as possible. Childhood is a celebration of attendance, not attempt. Break the rules, and punishment ensues. Conform, and be confirmed as a trusted member of society. The world is unstable. Politics is unpredictable. Technology is rampant. We can no longer believe our own eyes. Or ears. When we can no longer rely on our senses, those attributes that helped us survive the last 3,000 years, it's not a surprise that avoiding mistakes has become the currency of choice for many businesses. Plan and execute. A sea of grey in a world looking for hope. Leadership is the single greatest opportunity most of us will have to make a difference. I've said that before. Today, it's truer than ever. It comes with a responsibility which is to decide what that difference is. If you measure it in titles and awards, I promise you will be soon forgotten. Your name on a plaque at the bottom of a recycling bin or a landfill. But if you measure the difference you make in terms of how you react when people make mistakes, you will have established the foundations on which their creativity is unlocked. And that opens the door to ideas that no one has ever thought of before and to businesses that no one has ever seen. So, how do you react when people make mistakes? And what might you do differently?

    54 min
  6. David Rolfe of WPP - "The Producer"

    10/03/2025

    David Rolfe of WPP - "The Producer"

    Are you creating trust? David Rolfe is the Head of Production at WPP. When David and I debated last year, whether one person could someday make a Super Bowl ad, it felt like a provocation. This year, we both agreed it's an inevitability. Which brings with it a bigger question. How will we tell the difference between what's real and what's synthetic? And will it matter? And that's the moment when trust becomes everything. Trust in the makers, when we can no longer believe our own eyes. Trust in the curators that they'll tell us what we're looking at. And trust that technology can expand what's possible without stripping away the humanity that makes creativity matter. Trust is the fuel of the human journey, the thing we yearn for as we search for our tribe, for where we belong. And trust is the new currency. As Scott Galloway wrote in a recent newsletter, the Next Big Crisis in Confidence will come from our inability to distinguish human Intent. In a world optimized for optics, trust is the next scarce resource. And that's why trust is one of the 13 dimensions that we measure with our FORM Creativity Diagnostic. Why it shows up as a cornerstone of so many of the world's most innovative and creative companies. Because without trust, creativity shuts down. People won't share fragile ideas. They won't take risks, and they won't challenge the status quo. But when trust exists between leaders and teams, between companies and their audiences, then creativity is unleashed. It becomes safer to experiment, easier to collaborate, and becomes possible to build the kind of culture where bold ideas thrive. David Rolfe has always been one of the most thoughtful voices on production. Trust him when he tells you that we are barely scratching the surface of what is possible. And then make sure that you know whether trust is the currency at the heart of your organization. Or what you need to do to make sure that it is.

    30 min
  7. Phil Thomas of Informa Festivals - "The Connector"

    09/15/2025

    Phil Thomas of Informa Festivals - "The Connector"

    How connected do your people feel? Phil Thomas is the Chief Creative Officer of Informa Festivals. They're the company that owns Cannes Lions. And Phil has recently been named as Chairman of Comic Relief. One of the things that I've learned hosting this podcast is that the most powerful leaders rarely get remembered for their titles. They're remembered for how they made people feel. In this conversation with Phil, what stood out most weren't his achievements. It was his perspective on making people feel connected. As you'll hear, when you emphasize connection in your leadership, kindness, challenges, accomplishments, language shapes the culture, and the trust that follows becomes invaluable currency that maximizes creativity. Connection is also one of the 13 conditions that's measured by FORM, the creativity diagnostic that I've been developing. Because in every organization that I've studied, when people feel seen, heard, and respected, creativity is unlocked and businesses grow faster. And, memorably, this conversation with Phil is a reminder that connection isn't a soft skill, it's the foundation of creative leadership and the impact that that leadership leaves behind. How connected do your people feel to your organization? Do they feel seen, heard, and respected?

    41 min
  8. Neil Waller of Whalar Group - "The 'This' Leader"

    05/27/2025

    Neil Waller of Whalar Group - "The 'This' Leader"

    What's the 'this' in your business? Neil Waller is the Co-Founder and Co-CEO of Whalar Group. They're a global creator company. Whalar have done as much as anyone, and more than most, to catalyze the creator economy. And as you'll hear, it was inspired by a conversation with and an unforgettable provocation from Sir John Hegarty. But behind their success lies a characteristic that I find is often underappreciated and therefore in short supply, among most creative leaders. Commitment. I've mentioned before on this podcast that we've developed a diagnostic tool that can tell, is your company deliberately unlocking creativity or just hoping that it shows up? One of the gaps that shows up over and over again is a leader's commitment to the company's goals. Companies and leaders say one thing and then often do another. But when you find leaders that are truly committed to building a business that delivers world class creative thinking and answers, then how fast they can do that suddenly becomes an incredibly valuable conversation To create is to learn. And the faster we can do both, the better your business and the world becomes. So what's the 'this' in your business? And how committed are you to making it happen?

    55 min
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4.9
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About

We talk to leaders of the world's most disruptive companies about how they are jumping into the fire, crossing the chasm and blowing up the status quo. Leaders who've mastered the art of turning the impossible into the profitable.

Information

  • Creator
    Charles Day
  • Years Active
    2017 - 2026
  • Episodes
    523
  • Rating
    Explicit
  • Copyright
    © The Lookinglass Company, LLC d/b/a Fearless Creative Leadership. All rights reserved.
  • Show Website
    Fearless Creative Leadership

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