ON REALITY TV… With Dorinda Medley and Captain Sandy

ON REALITY TV… With Dorinda Medley and Captain Sandy

Author: Elizabeth Day and Sony Music Entertainment November 10, 2025 Duration: 14:13
If you know me at all, you’ll know that I am a huge advocate for reality TV. So what better reason to have a little trawl through my archives than to revisit some of my favourite interviews from reality TV stars? First, we hear from Dorinda Medley, known and adored from The Real Housewives of New York. Dorinda speaks about being approached to join Housewives shortly after losing her husband. She talks about her grief as a young widow and how the Bravo community supported her when she needed it most. Then, we turn to Captain Sandy from Below Deck Mediterranean. Sandy talks about life on board with production crews, the dynamics with her team, and - crucially - what she would put on her own preference sheet. Even if you’re not usually a reality TV fan, I hope this episode offers a glimpse into the humanity behind these shows - and how connection, vulnerability and growth can show up in the most unexpected places. Listen to Dorinda Medley’s full episode of How to Fail here: https://link.chtbl.com/Lf44HTRS Listen to Captain Sandy’s full episode of How to Fail here: swap.fm/l/CaptainSandy 🔗 LINKS + MENTIONS: Elizabeth’s Substack: https://theelizabethday.substack.com/ Join the How To Fail community: https://howtofail.supportingcast.fm/#content 💌 LOVE THIS EPISODE? Subscribe on Spotify, Apple or wherever you get your podcasts Leave a 5⭐ review – it helps more people discover these stories 👋 Follow How To Fail & Elizabeth: Instagram: @howtofailpod @elizabday TikTok: @howtofailpod @elizabday Website: www.elizabethday.org Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: howtofailpod.com 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 podcastadsales@sonymusic.com Learn more about your ad choices. Visit podcastchoices.com/adchoices

There's a quiet revolution happening in how we think about success, and How To Fail With Elizabeth Day is right at the heart of it. This isn't about schadenfreude or wallowing in misfortune. Instead, Elizabeth Day has created a space where the most interesting conversations begin with a simple, radical premise: our lowest moments are often our greatest teachers. Each episode, a guest-from celebrated artists and thinkers to everyday people with extraordinary stories-sits down to examine three significant failures from their own life. The magic lies in the excavation, as Elizabeth guides the discussion toward the unexpected wisdom and resilience that emerged from those setbacks. You'll hear the raw honesty in their voices, the laughter that comes with hindsight, and the profound clarity that failure can uniquely provide. This podcast, presented by Elizabeth Day and Sony Music Entertainment, digs into the messy, human stuff of life that connects us all, transforming shared vulnerability into a source of collective strength. It’s a reminder that the path to any meaningful achievement is rarely a straight line, but a series of instructive detours. The show actively invites listeners to reflect on their own stories, fostering a genuine community around the idea that we can all succeed better by understanding where we've previously stumbled. Tune in for conversations that are as comforting as they are challenging, and which might just change your perspective on what it means to live a well-lived life.
Author: Language: English Episodes: 100

How To Fail With Elizabeth Day
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