Part 1 of 2: 🎙“Why DEI Failed: Jessica Pettitt, Project 2025 and the Myth of Progress.”

Dec 28, 2025

Part 1 of 2:  🎙“Why DEI Failed: Jessica Pettitt on Project 2025 and the Myth of Progress.”

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What if the only way to fix DEI is to admit that almost everything we’ve been doing was performative from the start?
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Description

What if the entire conversation about DEI has been built on a fragile foundation of performance, guilt, and corporate fear, instead of anything real and human?

In this explosive first part of my conversation with Jessica Pettitt, we go straight into the political and cultural landmines that leaders pretend not to see.

Jessica is a seasoned DEI strategist, stand-up comic, and one of the few people in America who actually read the very controversial Heritage Foundation’s Project 2025 cover to cover. What she discovered inside that document, its history, its intentions, and yes, even the parts she agrees with, will challenge every assumption you have about where the United States is headed, culturally and politically. 

And we don’t stop there.

We dig into the dark psychology of humor, trauma in leadership, and why some people become rigid. In contrast, others become deeply compassionate, and how self-awareness is usually the biggest illusion in the room. We confront what happens when organizations pretend to care, when DEI becomes a corporate accessory, and when leaders fail to examine what they are responsible for.

This conversation isn’t about ideology.
It’s about reality.
And it might be the most honest discussion about DEI you’ve heard in years.

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🔥 In This Episode

• Why DEI failed, and why performance culture set it up to fail
• Jessica's surprising history with stand-up comedy, politics, and George Carlin ("Safety”)
• The dark psychology comedians and leaders share
• Why trauma creates either deep compassion or rigid absolutism in high performers
• The part of Project 2025 that shocked Jessica the most; because she agreed with it
• The danger of people who “think” they are self-aware
• Why most people outsource their beliefs instead of thinking
• The simplest question that exposes a leader’s real level of awareness: What are you responsible for?
• Why reading original sources matters more than consuming opinions about them
• What liberals misunderstand about conservatives, and what conservatives misunderstand about liberals
• How to have a real conversation across differences without buzzwords
• Why most organizations cannot tell the difference between harm reduction and performance branding

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👊 About Jessica Pettitt

Jessica Pettitt is the DEI strategist organizations call when their “good intentions” start causing real harm. She is the author of Almost Doing Good, a professional truth-teller, and one of the few people who has deeply analyzed Project 2025 from 1972 to today. Her approach blends candor, humor, deep research, and a refusal to hide behind Instagram-friendly platitudes. 

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🔗 Connect With Jessica Pettitt

Website & Project 2025 Resources: https://jesspettitt.com/project-2025
YouTube https://www.youtube.com/@JessPettitt  Playlist (32 chapter discussions): Search “Jess Pettitt Project 2025” on YouTube
Book: Almost Doing Good

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💥 Listen If You’ve Ever

• Wondered whether DEI actually works—or if it ever has
• Watched your company abandon initiatives it once claimed to “stand for”
• Felt uneasy about how polarized conversations have become
• Wanted to understand why people cling to rigid views
• Been curious about what Project 2025 actually says (not what people claim it says)
• Suspected that your definition of “responsibility” has been outsourced to someone else
• Wanted a conversation about politics and culture without extremism, performance, or bullshit

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💭 Reflection Question for Listeners

What are you truly responsible for, and how much of your worldview was handed to you instead of chosen?