Monica Lewinsky: On Shame, Survival & Reclaiming Her Story

How To Fail with Elizabeth Day June 25, 2025
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Monica Lewinsky is an activist, producer, and host of the powerful new podcast Reclaiming. At just 24, while working as a White House intern, she became the center of an international scandal—losing her career, privacy, and the future she had envisioned. What followed was a global, often brutal, public shaming that defined a generation. Now 51, Lewinsky has re-emerged as a leading voice on shame, bullying, and power dynamics—earning admiration from a new generation who’ve re-examined how she was treated through a more empathetic, culturally aware lens. In this deeply personal conversation, she reflects on reclaiming her identity, how she found purpose through pain, her struggles with perfectionism, and what it means to truly move forward. 00:00 Intro 01:32 Early Life and Career 03:12 Reclaiming Her Narrative 06:17 Reflections on Turning 50 11:19 First Memory of Failure 18:40 Struggles After the Scandal 23:12 Navigating Post-Scandal Job Search 23:58 The Fragility and Vulnerability of Public Scrutiny 25:03 Media Obsession and Public Perception 25:59 Surviving the Media Onslaught 27:16 Reflections on Love and Power Dynamics 30:22 The Impact of Betrayal and Somatic Therapy 35:50 The Handbag Business Venture 40:12 Lessons Learned and Final Thoughts Elizabeth and Monica answer YOUR questions in our subscriber series, Failing with Friends. Join our community of subscribers here: https://howtofail.supportingcast.fm/#content Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: howtofailpod.com All episodes in June are brought to you by @arlalactoFREE - all the taste, easier to digest. Listen to our bonus episode brought to by ArlaLactoFREE with Vicky Pattison here: https://link.chtbl.com/VickyPattison 🌎 Get an exclusive 15% discount on your first Saily data plans! Use code [howtofail] at checkout. Download Saily app or go to to https://saily.com/howtofail ⛵ How to Fail is an Elizabeth Day and Sony Music Entertainment Production. Find more great podcasts from Sony Music Entertainment at sonymusic.com/podcasts To bring your brand to life in this podcast, email [email protected] Learn more about your ad choices. Visit podcastchoices.com/adchoices Have something to share of your own? I'd love to hear from you! Click here to get in touch: howtofailpod.com    Follow us on 🎙️ - Instagram: https://www.instagram.com/howtofailpod?igsh=MWRvazJ0ZWxwNGQwZQ== - TikTok: https://www.tiktok.com/@howtofailpod?_t=ZN-8vVEkGwmBcM&_r=1

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