Ep. 127, Creativity Isn’t a Luxury Skill—It’s a Leadership Requirement with Melissa Dinwiddie
You don’t need more discipline to lead. You need less fear, fewer rules, and permission to make bad output on purpose.
EPISODE SUMMARY
So many leaders say they want creativity—but secretly punish it the moment it looks inefficient, awkward, or unfinished. In this episode, Jenn sits down with creativity instigator Melissa Dinwiddie to dismantle one of the biggest lies holding leaders back: that creativity is a luxury reserved for artists with time, talent, and confidence. Together, they explore what it actually takes to create sustainably—especially when you’re tired, responsible, and carrying real stakes. This isn’t about “finding your inner artist.” It’s about building trust with yourself, loosening perfectionism, and letting play lead the way again. If you’ve ever felt blocked, blank, or secretly jealous of people who “just create,” this conversation will feel like oxygen.
Here’s What’s in the Episode:
- [03:10] Why most people confuse talent with trust—and how that kills creativity before it starts.
- [07:45] The real reason perfectionism shows up (and why it’s not a motivation problem.)
- [12:30] How fear disguises itself as “being practical,” “being busy,” or “being professional.”
- [18:05] What leaders get wrong about play—and why play is actually a leadership skill.
- [23:40] How to create when you’re exhausted, overcommitted, or convinced you’re “not creative.”
- [29:15] A simple reframe that turns creative blocks into useful information.
- [34:50] Why joy and creativity are not rewards—but renewable resources.
Key Takeaway
Creativity builds confidence. You don’t wait until you feel ready. You create, and clarity follows. About the Guest: Melissa Dinwiddie Melissa Dinwiddie is an innovation strategist, keynote speaker, and recovering perfectionist who helps leaders create cultures where people can think, connect, and do their best work—especially under pressure. With a background as a Juilliard-trained dancer, professional visual artist, improviser, and jazz singer-songwriter, she brings a deeply human, embodied approach to leadership and organizational change. Melissa works with analytical leaders and teams to replace surface-level innovation tactics with small, practical experiments that build trust, psychological safety, and real momentum. Her work lives at the intersection of play, imperfection, and rapid learning—because that’s where joy, creativity, and performance actually thrive. She is the author of the forthcoming book Innovation at Work, a toolkit of micro-experiments designed to help leaders unstick teams and restore the joy of meaningful work. Connect with Melissa at melissadinwiddie.com. About the Host: Jenn Whitmer Jenn is an international keynote speaker, leadership consultant, and the founder of Joyosity™, helping leaders create positive, profitable cultures through connection, curiosity, and joy. With a background in communication, conflict resolution, and team dynamics, Jenn helps leaders and organizations navigate complex people challenges, reduce burnout, and build flourishing workplaces. Her insights have resonated with audiences worldwide, blending real-world leadership expertise, engaging storytelling, and a dash of humor to make the hard stuff easier. Whether on stage, in workshops, or with coaching clients, Jenn equips leaders with the tools they need to solve conflict, cultivate communication, and lead with purpose. Her book Joyosity and the Joyosity Works Playbooks offer leaders a fresh approach to joy at work that builds real results. jennwhitmer.com Jenn's Social
Resources & Links
Melissa's Latest book: Innovation at Work Innovation theater is killing your team’s potential. Your smartest people are stuck perfecting slides instead of testing ideas while competitors ship messy prototypes and learn what actually works. Find out more here. Get Joyosity and the Joyosity Works Playbook
- Joyosity: How to Cultivate Intense Happiness in Work & Life (Even If Things Are What They Are) Joy isn’t extra. Joy is how you thrive.
- This book gives leaders the tools to turn exhaustion into resilience and build cultures where work is a joy, people are whole, and organizations flourish.
- Joyosity Works Playbook: Practical Plays and Strategies for Joy at Work and Beyond is the official companion workbook to Joyosity to help you practice joy every day.
- Find direct links to purchase at your favorite booksellers at https://jennwhitmer.com/books.
Free 99:
- Joyosity Explorer Map → This map will guide you to understanding the deeper purpose and story you tell yourself about your work. Joy is linked to purpose and productivity increases by 20% or more when you directly link your purpose to your work.
Ready to Make a Plan:
- Joyosity™ Jumpstart → Get crystal clear on what you want, what’s in the way, and how to move forward with traction.
Starting the Journey:
- Enneagram Navigator → Stop guessing your type. In this 1:1 session, get clarity on your motivations and blind spots.
Ready to Dive In:
- Joyosity™ Intensive → A one-day transformative experience to realign with your values and build a practical plan for joyful leadership.
A Party for More:
- Bring Jenn & the Joy to Speak → Bring the spark (not just the spark notes!) to your whole team with contagious joy, practical tools, and plenty of laughter.
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