How To Fail With Elizabeth Day

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

This week we’re revisiting two deeply moving conversations that explore what it means to find hope in the face of profound adversity.

First, we hear from the 11-time world champion and a six-time Olympic champion, Sir Chris Hoy. He speaks with remarkable honesty about living with stage four prostate cancer, as well as the shock of discovering that his wife had been diagnosed with multiple sclerosis during the same period. He talks about finding hope, and appreciating the small things in life.

Then we hear from the legendary British children’s author, Michael Rosen, who reflects on the devastating loss of his son, Eddie, who died at the age of 18. He explains how talking about him now is in fact a relief.

These stories speak to resilience, love and the ways hope can survive even in the hardest of circumstances. Whether you are personally affected, or know of someone going through a tough time at the moment, I hope these conversations offer comfort and a fresh perspective.

Listen to Sir Chris Hoy’s full episode of How to Fail here: swap.fm/l/vkdUVszJnMghYNMSLFdO

Listen to Michael Rosen’s full episode of How to Fail here: swap.fm/l/3lr5HOsDIw6hgOnD7vgc

🔗 LINKS + MENTIONS:

Cancer Support UK: www.cancersupportuk.org

Bereavement Support: www.cruse.org.uk

Mental Health Support: www.samaritans.org and www.mind.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

Best known for her role as Queen Charlotte in Bridgerton, Golda Rosheuvel is an acclaimed actor of stage and screen. Her career spans powerful theatrical roles including Romeo and Juliet, Jesus Christ Superstar and a groundbreaking lesbian interpretation of Othello. She also stars in the spin-off series Queen Charlotte: A Bridgerton Story.

In this conversation, Golda speaks movingly about her childhood and family: how her mother, a white social worker, met her father, a Guyanese Anglican priest, by chance at a choir rehearsal in Jamaica. She reflects on discovering she was dyslexic, navigating rejection, experiencing racism, struggling with motivation - and even failing an early audition for Bridgerton. Plus: why representation is so important.

✨ IN THIS EPISODE:

00:00 Introduction

04:12 Impact of Representation and Public Recognition

08:39 Challenges with Dyslexia

21:15 Navigating Identity and Belonging

28:10 Professional Challenges and Identity

29:08 Casting and Industry Feedback

29:47 Facing Rejection and Overcoming Setbacks

30:32 Failed Auditions and Lessons Learned

31:45 Challenges of Racial Identity in Theatre

34:04 Progress in Representation and Diversity

35:35 Reflecting on Parental Influence

38:58 Navigating Personal and Professional Identity

40:36 Struggles with Exercise and Motivation

47:54 Final Thoughts and Legacy

💬 QUOTES TO REMEMBER:

‘I’m not half anything. I’m a whole... I found who I want to be.

‘I don't see [dyslexia] as a failure because it was never told to me that it was a failure... It was, “you see the world differently”. This is really exciting.’

‘Representation is important. We wanna see people who look like us, who we can relate to.’

🔗 LINKS + MENTIONS:

Part one of Bridgerton season four premieres on 29th January on Netflix; part two begins streaming on 26th February

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

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

📚 WANT MORE?

Gillian Anderson - on her failure to eat well or exercise and why she never wants to do what people tell her swap.fm/l/7NyZMzkfVOpGyDtlB6k0

Letitia Wright - on bullying, rejection, self-doubt, anxiety and depression. Plus how faith and friendship helped her turn those struggles into strength and purpose swap.fm/l/orHGF9VMU6s1FOH3bupc

💌 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 Golda 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