In this episode of Workday Playdate, Erin sits down with Catharine Savage to explore why failure might not be something to avoid after all. As an improviser, facilitator, educator, and performer, Catharine has spent years helping people discover that growth often lives on the other side of discomfort.

If you've ever avoided taking a chance because you were afraid to fail, this conversation offers a refreshing perspective on why mistakes can actually be fun.

Inside This Episode:

Why We Fear Failure So Much: Catharine and Erin unpack the stories we tell ourselves about failure and explore why so many high achievers struggle to take risks in the first place.
How Improv Changes Our Relationship with Mistakes: Drawing on her experience with The Second City and years of facilitating workplace workshops, Catharine shares how improvisation helps people build resilience, adaptability, and confidence through experimentation.
The Surprising Joy of Failing: Failure doesn't have to mean defeat. Catharine explains how reframing mistakes as data, stories, and opportunities can transform both our careers and our lives.
Building Psychological Safety Through Play: Erin and Catharine discuss why teams that normalize mistakes are often the most innovative, collaborative, and successful.
Taking Yourself Less Seriously: Some of the best learning happens when we let go of perfectionism. Catharine shares practical ways leaders can create space for humor, curiosity, and growth even in high-pressure environments.

What to Do Now:

Try Something You're Bad At: Pick one small activity this week that feels uncomfortable or unfamiliar. Give yourself permission to be a beginner and notice what you learn.
Celebrate a Recent Mistake: Reflect on a recent failure or setback. What did it teach you? Share the lesson with a colleague or friend.
Practice "Yes, And" Thinking: The next time something doesn't go according to plan, challenge yourself to ask, "Yes, this happened...and what might be possible now?"

About the Guest

Catharine Savage is a facilitator, educator, improviser, and performer with extensive experience helping individuals and teams build communication, adaptability, and leadership skills through the principles of improv. She performs with The Second City National Touring Company and facilitates professional development experiences through The Second City Works, bringing humor and humanity into workplaces across industries. In addition to her performance work, Catharine teaches and coaches others to embrace experimentation, navigate uncertainty, and find growth through failure. Before pursuing improv professionally, she worked in consulting and sales enablement, giving her a unique perspective on the challenges leaders face in today's workplace. Catharine is passionate about helping people become more resilient, collaborative, and willing to take risks—both on stage and at work.

Your Freebie

How do you lead through failure and uncertainty?

Today’s workplace demands adaptability, creative problem-solving, and leaders who can navigate uncertainty without freezing in perfectionism.

This quick quiz will reveal your unique approach to failure and uncertainty, plus give you simple ways to strengthen your adaptability muscles and help your team thrive when things don’t go according to plan.

Connect with Catharine Savage

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Connect with Erin Diehl

🌟 Learn more about Workday Playdate: https://www.learntoimproveit.com/podcast-page
🎤 Book Erin to speak: https://passionstruckspeakers.com/speakers/erin-diehl/
📚 Workshops & Team Experiences: https://www.learntoimproveit.com/experiential-training
💌 Learn more about Erin: https://www.itserindiehl.com/meet-erin
📱 For more information on improve it! visit www.learntoimproveit.com.

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