Episode Details

Sarah Cooper went viral for lip-syncing Donald Trump on TikTok — and suddenly, the world knew her face. From there came a Netflix special, a memoir, acting alongside Jerry Seinfeld, and guest-hosting Jimmy Kimmel Live.

But there was also everything people didn’t see: the disorientation of sudden fame, the pressure to keep performing, and the years of self-doubt that followed.

In this conversation, Sarah and Connor go beneath the viral moment and explore how comedy became her way of moving through pain, divorce, and reinvention. They unpack how self-awareness fuels creativity, how intuition beats optimization, and how humor itself reveals the deeper work of resilience and self-leadership.

CHAPTERS

Chapters

• 00:00:00 Intro — Sarah Cooper on success, doubt, and meaning
• 00:01:13 From Google to comedy
• 00:04:36 Going viral & getting humbled
• 00:07:22 The hangover after fame
• 00:11:03 Perfectionism, family, and learning to fail
• 00:15:43 Rediscovering herself after divorce
• 00:18:10 Comedy as power & perspective
• 00:21:24 The human voice in an AI age
• 00:27:01 Fame, isolation, and honesty
• 00:32:04 Leaving Google and finding courage
• 00:38:59 Manifestation gone wrong (the SNL story)
• 00:45:00 Group therapy & saying what’s real
• 00:58:25 Legacy — making people feel less alone

IS THIS WORKING?!

What if the most interesting thing about work isn’t what we do—but what it does to us?

Is This Working?! is about meaningful work and the messy humans who do it. Host Connor Diemand-Yauman talks to the leaders, builders, and creatives navigating the chaos through the moments they question everything and show up anyway.

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