Sophie Habboo - I Wish I Had More Boundaries

Sophie Habboo - I Wish I Had More Boundaries

Author: Elizabeth Day and Sony Music Entertainment April 8, 2026 Duration: 47:18
This week we are joined by podcasting royalty, Sophie Habboo! Habboo found fame on Made In Chelsea, E4’s structured-reality show following the lives of affluent 20-something Londoners where she met fellow cast-mate Jamie Laing in 2017. The two began dating - and then launched a media empire. Their podcast, NearlyWeds was an instant hit and was rebranded as NewlyWeds when they got married in 2023. Habboo now runs the hugely successful JamPot podcast production company with her husband and the two served as executive producers on Raising Chelsea, a new three-part Disney+ documentary following the couple as they face the messy, scary and comic reality of becoming parents for the first time. In this episode Sophie talks openly about her feelings of overwhelm and anxiety in the run up to their wedding, her ADHD diagnosis, the challenges of being a new mum and the importance of setting boundaries. ✨ IN THIS EPISODE: 03:50 Family Roots And Motherhood 06:39 Ziggy Bay And Marathon Madness 08:35 Failure One: No Boundaries 10:23 One Day Office Job Disaster 16:01 Wedding Overwhelm And ADHD 20:52 Insecurities and Social Situations 21:53 Anxiety and Imposter Feelings 23:05 Therapy and Psychic Rituals 24:18 Sponsor Break The Testaments 26:12 Motherhood and Fear of Failing 29:36 Love Story With Jamie 33:54 A Surprise Voice Note 💬 QUOTES TO REMEMBER: I do always have imposter syndrome and maybe even as a mother... I really struggle with ‘mum guilt’. Had I been diagnosed with ADHD earlier, I would've been able to understand and have more compassion for myself. 🔗 LINKS + MENTIONS: Raising Chelsea is available to watch now on Disney+ The Testaments, a new Hulu original series, streaming April 8 exclusively on Disney+ Join the How To Fail community: www.howtofail.supportingcast.fm/#content Elizabeth’s Substack: www.theelizabethday.substack.com 📚 WANT MORE? Jamie Laing - on anxiety, insecurity and the pressure of fame. Plus his ‘failure’ to have a long-term relationship [spoiler alert: it all worked out just fine!]: swap.fm/l/QXKrzzpg5hULgBpXWMBY Dorinda Medley - on young widowhood, dealing with anger and what The Real Housewives of New York taught her: swap.fm/l/Q3MPl0zGn9MShaUdGEi4 💌 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: @elizabday TikTok: @howtofailpod Podcast Instagram: @howtofailpod Website: www.elizabethday.org Elizabeth and Sophie answer listener questions in our subscriber series, Failing with Friends. Join our community of subscribers here: www.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 Production & Post Production Coordinator: Eric Ryan Engineer: Matias Torres Assistant Producer: Shania Manderson Senior Producer: Hannah Talbot Executive Producer: Alex Lawless 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
Podcast Episodes
Michelle Yeoh - On typecasting, fertility and THAT Oscars speech [not-audio_url] [/not-audio_url]

Duration: 53:19
Michelle Yeoh has created a legendary body of work that defies easy categorisation. You’ll know her from cult classic Kung Fu Cinema, Everything Everywhere, All At Once - the film that made her the first Asian woman to b…
ON PARENTING…with Andy Cohen and Caitlin Moran [not-audio_url] [/not-audio_url]

Duration: 13:34
Today, we’re chatting all about parenting on How To Fail! We’ll be revisiting some of the most meaningful moments from the archive - the ones that can bring a fresh insight, thoughtful perspective and a sense of comfort…
Kelly Brook -  I’m In My Don’t Give A Damn Era! [not-audio_url] [/not-audio_url]

Duration: 52:55
Just a heads-up that in this episode we talk about late miscarriage. I am so grateful to Kelly for opening up about something that affects and speaks to so many of us - it’s a beautiful conversation but if you’re feeling…
ON REALITY TV… With Dorinda Medley and Captain Sandy [not-audio_url] [/not-audio_url]

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,…
Malala Yousafzai - I Am Not Who You Think I Am [not-audio_url] [/not-audio_url]

Duration: 52:12
You might think you know about Malala. But you’d be wrong. For so many years, she stood as a symbol of resistance: the teenage girl who was shot by the Taliban for insisting on the right to go to school and who later won…
ON EMBARRASSING MOMENTS… With Dan Levy and Phoebe Waller-Bridge [not-audio_url] [/not-audio_url]

Duration: 11:34
Welcome back to this How to Fail episode where we journey through the archive to revisit some of the best bits. This week we’re keeping it light and taking a look at some of the funniest and most entertaining embarrassin…
Jon Bon Jovi - Fame is a liar and a thief [not-audio_url] [/not-audio_url]

Duration: 52:18
We have a bonafide legend on How To Fail: the American singer, songwriter, guitarist, actor and philanthropist who, along with his band, sold more than 130 million albums and performed in over 50 countries for more than…
ON BODY IMAGE… With Martine Wright and Paloma Faith [not-audio_url] [/not-audio_url]

Duration: 18:48
Body image is a common theme on How to Fail. It’s something everyone at some point has either struggled with personally, or knows someone who has. We hear from Paloma Faith on the topic - she speaks about being thrown ou…
Denise Welch - I Got Sober For Love [not-audio_url] [/not-audio_url]

Duration: 59:28
You might know Denise from Coronation Street, Waterloo Road, or as the winner of Celebrity Big Brother in 2012 and a regular panelist on ITV’s flagship panel chat show, Loose Women, or remember when she won Celebrity Big…
ON SCHOOL… With Jamie Dornan and Bernie Sanders [not-audio_url] [/not-audio_url]

Duration: 18:19
I’m diving into the back catalogue, bringing you moments of insight, laughter and truth from past guests. These themed episodes are a chance to reflect on the universal experiences that connect us all. This week we’re lo…