How To Fail With Elizabeth Day

This episode includes discussion of eating disorders, including anorexia and bulimia. Listener discretion advised.

This might be one of the most powerful conversations I’ve ever had on How To Fail. I don’t say that lightly - I’ve had some amazing guests - but there’s something about how Jennette puts the female experience into words that I find truly electrifying.

Raised Mormon in Orange County, Jennette was just six when her mother decided she would become an actor. What followed was a difficult, abusive childhood, which she chronicled with unflinching honesty in her 2022 memoir, I’m Glad My Mom Died - a book that spent more than 90 weeks on the New York Times bestseller list.

Her new novel, Half His Age, follows 17-year-old Waldo as she embarks on an affair with her 40-year-old creative writing teacher. It’s a startling, powerful story about discomfort, agency and self-determination and it became a Sunday Times Number One bestseller in its first week!

In this episode, we talk about her upbringing, her experience of disordered eating, the writing process and the grounding partner she’s been with for nine years (who I was lucky enough to meet). Plus: setting boundaries, finding your voice, rage, recovery and autonomy.

Recorded in our London studio.

✨ IN THIS EPISODE:

00:00 Introduction

03:27 Speaking Up and Setting Boundaries

04:15 Reception of 'Half His Age'

07:22 Exploring Mormonism and Guilt

14:36 Failures and Creative Process

30:09 Calorie Restriction Lessons from My Mother

30:58 First Encounter with Anorexia

32:45 The Turning Point: Mother's Death and Recovery

32:58 Struggles with Bulimia

35:41 Therapy and the Road to Recovery

36:47 Understanding the Value of Eating Disorders

38:59 Healing Through Relationships

42:58 Finding My Voice and Inner Peace

💬 QUOTES TO REMEMBER:

I think oftentimes a woman is perceived as difficult if the person around her can't meet her standards.

It’s time that women start speaking up in any capacity - and not worrying about being 'too much'.

There is nothing more powerful than a woman's intuition. I believe our bodies have inherent knowledge... denying our bodies is nothing but a disservice to a better life path for ourselves.

If you feel resentment, it's time to set a boundary.

🔗 LINKS + MENTIONS:

Jennette’s new book Half His Age is available to buy now

Join the How To Fail community: https://howtofail.supportingcast.fm/#content

Elizabeth’s Substack: https://theelizabethday.substack.com/

📚 WANT MORE?

Dolly Alderton – writing personal truth and navigating public scrutiny swap.fm/l/XM98joc3GFEMTsLfkEfR

Matt Haig – mental health and transforming suffering into storytelling swap.fm/l/amHeyBr7x2jg3Isw3JxG

Jameela Jamil – body image, disordered eating and unlearning harmful conditioning swap.fm/l/D0j8oJQ52OwiJu6W3T4o

💌 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 Jennette (who is a naturally brilliant agony aunt) answer listener 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

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 [email protected]
Learn more about your ad choices. Visit podcastchoices.com/adchoices

Families are fascinating: how those first bonds shape our understanding of love, security and ourselves. In this episode, we revisit episodes with Bella Freud and Danny Dyer, who each open up about the simultaneous beauty and complexity of family life.

Bella Freud, speaks about losing both of her parents to cancer within a week. As the great granddaughter of Sigmund Freud and the eldest sibling, she reflects on a complex childhood, the responsibilities she carried and how grief reshaped her sense of identity.

Secondly, we hear from Danny Dyer, who shares what it was like growing up on a council estate with a single mother. He discusses the shock of discovering his father had another family and how the absence of love in his early years shaped the devoted parent he is today.

Family dynamics can feel messy and taboo, but I hope this episode offers reassurance, validation and insight into the ties that form us first and stay with us for life.

Listen to Bella Freud’s full episode of How to Fail here: swap.fm/l/mQntNELQPRhZ9CjFQO77

Listen to Danny Dyer's full episode of How to Fail here: swap.fm/l/L192dU5DZHQnCUjFWuX8

🔗 LINKS + MENTIONS:

Family Support: www.family-action.org.uk

Elizabeth’s Substack: theelizabethday.substack.com

Join the How To Fail community: 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 [email protected]

Learn more about your ad choices. Visit podcastchoices.com/adchoices
Learn more about your ad choices. Visit podcastchoices.com/adchoices

Mo Gilligan started out working in retail (think Jo Malone and Levi’s) but quit in 2018 when his online comedy videos went viral. The leap paid off - sell-out tours across the UK, a late-night entertainment show on Channel 4 and his own breakout format The Lateish Show with Mo Gilligan, which earned him the first of three BAFTA wins. Netflix specials, world tours, primetime TV and a podcast soon followed.

Now in 2026, Gilligan is launching the biggest year of his career to date with a global tour, a major new partnership with Netflix and a feature documentary which will offer a glimpse behind the scenes of the 37-year-old at the top of his game.

In this episode, Mo opens up about being a dad to his six-month-old daughter and two-year-old son, the pressure of representing the Black British community in stand-up and the debt that shadowed him for years.

✨ IN THIS EPISODE:

00:00 Introduction

03:51 Retail Experience and Its Influence

06:11 Audience Interaction and Respect

09:13 School Struggles and Dyslexia

18:14 Family, Fatherhood and Financial Lessons

25:19 The Standup Struggle

26:37 Credit Card Chaos

31:12 The Viral Breakthrough

33:35 Touring Triumphs and Tribulations

36:04 Code Switching and Representation

39:43 Handling Success and Praise

45:51 Family and Future Plans

💬 QUOTES TO REMEMBER:

I really wanna make people feel cool. I think it’s the nicest feeling ever.

Knowing that I am my children’s universe... That is such a gift that I didn’t know I needed to have.

I find it hard to listen to praise about myself. I find it very, very hard... I'm always trying to move on to the next one.

🔗 LINKS + MENTIONS:

Get Mo’s tour tickets here: mogilligan.com/mo-live

Mo’s new Netflix show is available to watch now: Mo Gilligan - In the Moment

Join the How To Fail community: https://howtofail.supportingcast.fm/#content

Elizabeth’s Substack: https://theelizabethday.substack.com/

📚 WANT MORE?

Ashley Walters - on growing up fast, struggling with self-destruction and how accountability, therapy and fatherhood helped him rebuild his life and career. Fun fact: Ashley and Mo both went to the same school and had the same inspirational drama teacher! swap.fm/l/ksDRiLDV1iOXHRTTsdJ5

Miranda Hart - on public embarrassment, private anxiety and chronic illness. Plus: how learning to accept herself became her greatest success swap.fm/l/oTScN30b80GflJtO4rgu

Fern Brady - another stand-up who has experienced the precariousness of the industry and battled debt early in her working life swap.fm/l/cmeompBv7EHK20enmwbS

💌 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 Mo answer listener 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

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 [email protected]
Learn more about your ad choices. Visit podcastchoices.com/adchoices

We’re taught that love should happen early, and if it doesn’t, something’s gone wrong. But what if that’s not true?

In this episode, we hear from past How to Fail guests who found love later, or in their own time. Luke Evans reflects on meeting his soulmate in his forties and Dolly Alderton talks about heartbreak, celibacy to reassess the role of sex and romance in her life and learning that sitting with uncertainty can be the bravest choice.

I met my husband in my late thirties and I've found that trusting your own timing is often what leads to real love. I hope this is helpful for those unsure of what’s next.

Listen to Luke Evan’s full episode of How to Fail here: swap.fm/l/2AAJhVeDNGdKIJGdznR9

Listen to Dolly Alderton’s full episode of How to Fail here: swap.fm/l/XM98joc3GFEMTsLfkEfR

🔗 LINKS + MENTIONS:

Elizabeth’s Substack: theelizabethday.substack.com

Join the How To Fail community: 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 [email protected]

Learn more about your ad choices. Visit podcastchoices.com/adchoices
Learn more about your ad choices. Visit podcastchoices.com/adchoices

A few years ago, Shabaz Ali was a chemistry teacher in Blackburn. Today, he’s one of the internet’s most beloved creators, best known as Shabaz Says, with millions of fans and a knack for skewering the most outrageous (and often tasteless) displays of online excess.

Since quitting the day job, Shabaz has launched a podcast, performed at the Edinburgh Fringe and published his book I’m Rich, You’re Poor. Beneath the humour though, there’s always been something more serious at play: a sharp commentary on the psychological erosion that comes from spending too much of our lives online.

In this episode, we talk about Shabaz’s upbringing, being bullied at school, how his taxi-driver Dad didn’t even realise his son was famous until recently and why no-one should ever spend £10,000 on an outfit.

✨ IN THIS EPISODE:

00:00 Introduction

03:03 The Impact of Social Media on Youth

05:14 Navigating Imposter Syndrome and Success

10:53 Embracing Authenticity and Overcoming Criticism

12:46 Growing Up in Blackburn

15:45 Challenges of Intersectional Identity

22:36 Family Perspectives and Cultural Expectations

24:04 Struggles with Poverty

25:20 Empathy

30:15 From Teacher to Social Media Star

31:24 Unexpected Career in the Hospital Morgue

33:38 Finding Viral Success Online

37:16 Representation and Finding Your Voice

💬 QUOTES TO REMEMBER:

You can be a man and still speak up for women's rights. You don't have to be a black person to speak up for black people. You don't have to be trans to speak up for trans rights.

How you present yourself is always how the world's going to treat you.

[Death] definitely gave me an appreciation for life. It gave me appreciation for human beings... I have so much love to give for humanity.

I don’t care if I’m palatable for you.

🔗 LINKS + MENTIONS:

Shabaz’s book, I'm Rich, You're Poor - is out now

Join the How To Fail community: https://howtofail.supportingcast.fm/#content

Elizabeth’s Substack: https://theelizabethday.substack.com/

📚 WANT MORE?

John Bishop - on how insecurity, self-doubt and feeling like an outsider shaped both his comedy and his life. Plus: almost getting divorced but then changing his mind swap.fm/l/wRGKwuonJFQoujFlmDHI

Celeste Barber - on using humour to challenge impossible beauty standards, early struggles with rejection and how embracing authenticity changed her life swap.fm/l/qLmwfjyeSolWuFeaHGdt

💌 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 Shabaz answer listener 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

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 [email protected]
Learn more about your ad choices. Visit podcastchoices.com/adchoices