Ep 10 | Why Does It Feel So Wrong To Fail?

Season 1, Episode 10: Why Does It Feel So Wrong to Fail at Work?

Episode Description:

Failure is inevitable. But why does it still feel so wrong?

In this heartfelt and celebratory finale of Why Does It Feel So Wrong to Be Human at Work?, hosts Pinaki Kathiari and Chris Lee dive into why failure carries so much emotional weight at work—and why that needs to change. With humor, humility, and personal stories, they reflect on childhood expectations, leadership norms, and the organizational fear of getting things wrong.

They explore:

• The roots of failure-shame and how we learn it in childhood
• How perfectionism, risk aversion, and toxic expectations show up in corporate culture
• The difference between good failure and careless mistakes
• How leaders can create psychological safety to foster innovation
• What sports, parenting, and start-ups teach us about falling forward
• Why quitting can be the smartest move—and how to know when it’s time
• The importance of experimenting, iterating, and letting go of perfection

This isn’t just a conversation about failing, it’s about learning, evolving, and building workplaces where failure is seen as a teacher, not a threat.

 

Timestamps:

• 00:00 – Why we fear failure from a young age
• 08:00 – Personal stories: parenting, pressure, and resilience
• 15:00 – Failure in corporate culture: old school vs. evolving norms
• 25:00 – The power of bad ideas and the risk of perfectionism
• 35:00 – Organizational shame, quitting, and "sunk cost" bias
• 45:00 – Amy Edmondson’s Right Kind of Wrong and failing well
• 55:00 – Design thinking, MVPs, and building fast to learn fast
• 01:05:00 – Michael Jordan, JK Rowling, and legendary "failures"
• 01:15:00 – Making peace with imperfection, embracing small wins
• 01:20:00 – Thank you, community: Final thoughts on being human at work

 

Books & Resources:

Right Kind of Wrong by Amy Edmondson

Thinking in Bets by Annie Duke

The Dip by Seth Godin

Blink by Malcolm Gladwell

 

Mic-Drop Moments:

“Failure isn’t the opposite of success. It’s the staircase to it.”

“We fear failure because we were taught it meant we were wrong—not just wrong, but bad.”

“Let’s fail fast, fail cheap, and succeed sooner.”

“Every step you take that doesn’t work is still a step forward.”

 

Connect with Us:

Pinaki Kathiari – LinkedIn | Local Wisdom

Chris Lee – LinkedIn | Gallagher Communication

 

Special Thanks:

Huge gratitude to everyone who joined us for this first season—our listeners, our guests, and our production team. Thank you for making space for real conversations about what it means to be human at work. And a special thanks to Local Wisdom for sponsoring this season and leading the way in people-first communication.

 

Your Turn:

What’s a failure that helped you grow the most? What’s your organization’s attitude toward mistakes? Share your thoughts with us at whydoesitfeelsowrong.com or on LinkedIn using #WhyDoesItFeelSoWrong.

Special thanks to digital communication agency Local Wisdom (www.localwisdom.com) for really believing in our mission and making this podcast possible. 

If this episode made you think differently, laugh, or even yell out loud, we want to hear about it! Connect with us on LinkedIn, and don’t forget to rate, review, and share – maybe with your work bestie… or even your boss if you're feeling bold.

 

We also bring these important conversations to conferences and private workshops, creating space for real, meaningful change. Take the first step at www.whydoesitfeelsowrong.com.