Scaramucci’s 11-day tenure as the White House Communications Chief under President Donald Trump’s first term ended in a blaze of recrimination. Scaramucci was advised by a PR consultant to disappear for five years. He refused - and reinvented his career.

Now, he is the co-host of the US version of The Rest is Politics podcast alongside British journalist Katty Kay.

After Harvard Law School, he joined Goldman Sachs and built a career in finance, eventually founding the investment firm SkyBridge Capital.

In this revealing conversation we discuss what working on Wall Street in the 80s was like, getting fired from Goldman Sachs, his failed first marriage, not being there for his son’s birth, getting fired from The White House and rebuilding his current marriage.

His book, All the Wrong Moves, looks at how three catastrophic decisions and years of ‘sh*tshow politics’ led to Trump.

IN THIS EPISODE:

00:00 Introduction montage

03:22 Learning optimism and pronoia

05:02 Self forgiveness after failure

06:40 Growing up and getting to Tufts

11:58 Why he wrote the book

14:03 Fired then rehired at Goldman

25:23 Money mindset and marriage cracks

30:48 Work Taxes Burnout

31:26 Marriage Neglect Regrets

34:07 Conflict Avoidance Trap

34:55 Affair Self Forgiveness

37:46 Fatherhood After Divorce

40:44 Trump Ego Decision

45:00 Firing from The Whitehouse

57:03 Rebuilding and Looking Ahead

💬 QUOTES TO REMEMBER:

When bad things happen, take a step back, and get into a channel that is the adult channel. Act in a rational way.

I trained my brain to be optimistic.

If you’re not careful, wealth can make you very depressed and lonely.

Trump's bullying reminded me of my dad… but I was better prepared for it.

🔗 LINKS + MENTIONS:

Anthony’s book, All the Wrong Moves, is available to buy now: www.penguin.co.uk/books/476667/all-the-wrong-moves-by-scaramucci-anthony/9781847929235

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

Elizabeth’s Substack: www.theelizabethday.substack.com

📚 WANT MORE?

Bernie Sanders - swap.fm/l/pH8V6cBejDnhH47ega6D

Andy Burnham - swap.fm/l/IpwatiJ5cM1h0UfcyFiA

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Elizabeth and Anthony answer listener questions in our subscriber series, Failing with Friends. Join our community of subscribers here: https://lnk.to/7i0moR

Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: askhowtofail.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]

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Luke Evans and Sarah Solemani join Elizabeth to talk about the journey of Elizabeth’s 2017 novel The Party to its new five-part ITV adaptation. 

Luke stars as the show’s protagonist, Martin Gilmour, and Sarah stars as his wife, Lucy… oh and she also brilliantly adapted the novel for screen. 

The trio discuss the making of this exciting new drama for TV, how Luke discovered the book and kick-started the process and what the show is about. They discuss themes including: sexuality, the class system in the UK, shame, women leading production, culture on sets in today’s world and friendship. 

This bonus episode is brought to you by @arlalactoFREE - all the taste, easier to digest.

IN THIS EPISODE

00:00 Introduction

01:42 Luke Discovers the Novel

02:51 Finding the Screenwriter

04:45 Adapting Into Five Episodes

07:13 What The Party Is About

09:44 Casting Lucy and Onscreen Marriage

13:04 Collaboration and Set Rewrites

18:09 Women Leading the Production

19:35 Set Culture and Final Day Speech

21:15 Author Visits Set and Craft Details

22:26 Friendship, Desire and Identity

25:08 Class, Shame and Final Takeaways

WANT MORE?

Luke Evans - swap.fm/l/2AAJhVeDNGdKIJGdznR9 

 LINKS + MENTIONS:

• The Party starts Sunday 11th October 9pm on ITV1 and ITVX. The series airs for three consecutive nights: Sunday, Monday and Tuesday, concluding with the fourth and final episode the following Sunday 18th and Monday 19th. Or you can binge all five episodes on ITVX. 

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

• Elizabeth’s Substack: www.theelizabethday.substack.com

• Subscribe on Spotify, Apple or wherever you get your podcasts

• Leave a 5⭐ review – it helps more people discover these stories

• Instagram: @elizabday

• TikTok: @howtofailpod

• Podcast Instagram: @howtofailpod

• Website: www.elizabethday.org

Join our community of subscribers here: https://lnk.to/7i0moR 

Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: askhowtofail.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]

LOVE THIS EPISODE? Follow How To Fail & Elizabeth:

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Bonnie Garmus was 64 when her debut novel, Lessons in Chemistry, was published. It went on to sell more than eight million copies, spend almost two years on the New York Times bestseller list, was translated into more than 40 languages and become an eight-part Apple TV+ series. At its centre was Elizabeth Zott, a fiercely intelligent, forthright chemist turned 1950s TV cooking star.

Bonnie and I talk about the misogyny that inspired Lessons in Chemistry, her love of dogs, working through a stutter, adopting her two daughters from China and what it took to overcome years of rejection.

Her new novel, Peck & Peck, is out in the UK on 13 October.

IN THIS EPISODE:

00:00 Intro

03:41 Arts Versus Science

05:44 Sexism Sparks Novel

08:58 Greed And AI Warning

12:19 Dogs Behind Characters

16:30 Childhood Failures

30:26 Living With A Stutter

31:50 Letters And Workarounds

32:53 Adoption Journey To China

36:10 What Adoption Really Means

37:23 Family Bonds And Fate

39:17 Jeopardy Husband Spotlight

40:10 98 Rejections And Resilience

47:05 Finding An Agent And Writing Life

💬 QUOTES TO REMEMBER:

I’ve had a lot of dogs in my life, and not a single one has disappointed me.

I never look back on my career and think I have regrets.

I had a therapist who was a stutterer… he gave me the courage to embrace it, and then I got better.

🔗 LINKS + MENTIONS:

Bonnie’s new novel Peck & Peck is available to pre-order now: www.waterstones.com/book/peck-and-peck/bonnie-garmus/9781786588975

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

Elizabeth’s Substack: www.theelizabethday.substack.com

📚 WANT MORE?

Alain De Botton - swap.fm/l/dnU4ieYPW7eCbesQFNSf

Chimamanda Ngozi Adichie - swap.fm/l/YiA3DPR1awzdCrHfEMfPv

💌 LOVE THIS EPISODE?

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👋 Follow How To Fail & Elizabeth:

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Podcast Instagram: @howtofailpod

Website: www.elizabethday.org

Elizabeth and Bonnie answer listener questions in our subscriber series, Failing with Friends. Join our community of subscribers here: https://lnk.to/7i0moR

Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: askhowtofail.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

Russell T Davies has spent decades creating some of Britain’s most beloved and groundbreaking television. After studying English at Oxford, he went from writing for children’s programmes and Coronation Street to creating Queer As Folk in 1999 - a show that changed the conversation around gay representation on TV. Since then, he’s written hit after hit, from Bob & Rose and A Very English Scandal to Years and Years, It’s A Sin and his hugely successful revival of Doctor Who. He’s won four BAFTAs and was awarded an OBE in 2008.

In this episode we talk about where his obsession and passion for TV came from, how his exceptionally busy mind works, losing his husband to a brain tumour, his love of Dr Who and…finding love again.

His new memoir, The Queerest of Folk, is out on 8th October.

IN THIS EPISODE:

00:00 Intro

02:35 TV Obsession Origins

03:24 Memoir and Andrew

08:35 AIDS and Its a Sin

10:36 Queer as Folk Shockwaves

12:37 Failure to Drive

16:45 Writing in Images

28:05 Early Illustration Gigs

28:54 Obsessed With Drawing

30:20 Losing the Habit

31:52 Comics and Story Beats

33:54 Writing Geniuses Doctor Who

37:13 Staying a Fan

41:41 Legacy and Family Roots

49:59 Aging Love and Goodbye

💬 QUOTES TO REMEMBER:

When I dream I invent people who don’t exist.

I’ve saved for decades, I saved for a rainy day, and then one day it rained.

Please never get rid of the Tardis.

🔗 LINKS + MENTIONS:

Russell’s memoir, The Queerest Of Folk is available to buy now: uk.bookshop.org/p/books/the-queerest-of-folk-a-life-in-television-russell-t-davies/a290496f474a1f8c

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

Elizabeth’s Substack: www.theelizabethday.substack.com

📚 WANT MORE?

Phoebe Waller-Bridge - swap.fm/l/gTCOCJUmXX9t22mTABSa

Bernardine Evaristo - swap.fm/l/EH5cvO3uPdNCQN9tYyiJ

💌 LOVE THIS EPISODE?

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Website: www.elizabethday.org

Elizabeth and Russell answer listener questions in our subscriber series, Failing with Friends. Join our community of subscribers here: https://lnk.to/7i0moR

Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: askhowtofail.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

Sir Paul Smith is one of Britain’s most iconic fashion designers, renowned for his sharp tailoring and his sartorial flair. His clothes have an innate sense of mischief: brightly coloured linings, unexpected stripes and a determination never to take themselves too seriously. His devoted clients include Gary Oldman, Bill Nighy and Matty Healy, who wore a Paul Smith suit for his recent wedding.

Behind the stripes and the suits is a man with a simple life philosophy: stay humble, work hard, be kind. On this episode we talk about the cycling accident that set him on a path to fashion and how he’s kept his global business independent for 56 years. Plus, the secret to a long marriage, what tailoring teaches him about people’s insecurities - and why he wore a suit every day during the Covid lockdowns.

IN THIS EPISODE:

00:00 Intro

03:40 Tailoring for Everyone

06:48 The Pink Wall Story

08:31 Stripes and Reinvention

10:20 Turning 80

11:33 Cycling Freedom and Family

18:20 Crash That Changed Everything

24:20 Pauline Sets The Standard

25:19 Keeping Love And Work Balanced

26:19 Step Parenting And Playfulness

27:28 The Trap Of Comparison

32:43 Brexit COVID And Staying Independent

36:02 Choosing The Right Collaborations

37:21 Believing Your Own Hype

42:47 Creativity Legacy And Farewell

💬 QUOTES TO REMEMBER:

Pauline [my wife] set the standard - it’s been very important for longevity.

A successful relationship is about balance. Knowing when to talk, when to listen… and have both feet on the ground.

The danger is losing your focus, and worrying too much about ‘them’.

🔗 LINKS + MENTIONS:

Sir Paul Smith’s Memoir ‘Threads’ is available to buy now: www.paulsmith.com/uk/threads-by-sir-paul-smith-special-edition-book

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

Elizabeth’s Substack: www.theelizabethday.substack.com

📚 WANT MORE?

Edward Enninful - swap.fm/l/NOAt5NDZeBTgX6qZUWpB

Bella Freud - swap.fm/l/mQntNELQPRhZ9CjFQO77

💌 LOVE THIS EPISODE?

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👋 Follow How To Fail & Elizabeth:

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Podcast Instagram: @howtofailpod

Website: www.elizabethday.org

Elizabeth and Sir Paul answer listener questions in our subscriber series, Failing with Friends. Join our community of subscribers here: https://lnk.to/7i0moR

Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: askhowtofail.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 episode contains references to and descriptions of eating disorders.

Louise O’Neill is a bestselling, award-winning Irish author whose fearless writing has helped shape modern feminism. Her fiction is taught on the Irish curriculum and Paul Mescal starred in a critically acclaimed stage adaptation of her work. Her second novel, Asking For It, catapulted her into the public eye in 2015.

Now, with her eighth book, A Bigger Life, O’Neill turns that same unflinching gaze on herself. Her memoir follows the extraordinary dating experiment she embarked on in her late 30s after the end of a long-term relationship: dating a different man every night, across three cities - Paris, London and New York. What began as a challenge, inspired by something her father said, became an unexpected journey of self-discovery.

In this episode we discuss topics covered in her memoir, A Bigger Life, including: finding hope after heartbreak, pressure on women, extraordinary dating experiences and recovering from a debilitating two-decade-long eating disorder.

A Bigger Life is out this month.

IN THIS EPISODE:

00:00 Introduction

03:24 Writing Her First Memoir

04:58 Roots in West Cork

08:21 Dating for a Bigger Life

09:26 Choosing Hope After Heartbreak

13:22 Marriage Expectations and Milestones

16:57 Beauty Pressure and Aging Fears

27:12 Fear of Vulnerability

28:48 Aging and Shame

30:34 Trusting Your Instincts

33:35 The Millionaire Date

36:40 Recovery After 17 Years

42:57 Rewiring the Mind

48:35 Good Girl Burnout

52:07 Redefining Success

💬 QUOTES TO REMEMBER:

I didn’t want the break-up to define me.

Life falls apart around us, and then we have to rebuild. The trick is to keep your heart soft.

If I’m setting the narrative, I want it to be hopeful .

I had to rewire my brain - I had to become an entirely new person. Then it became second nature.

🔗 LINKS + MENTIONS:

Louise O’Neill’s memoir A Bigger Life is out now: https://harpercollins.co.uk/products/a-bigger-life-louise-oneill?variant=55970156118395

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

Elizabeth’s Substack: www.theelizabethday.substack.com

📚 WANT MORE?

Dolly Alderton - swap.fm/l/XM98joc3GFEMTsLfkEfR

Caitlin Moran - swap.fm/l/CaitlinMoran

💌 LOVE THIS EPISODE?

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👋 Follow How To Fail & Elizabeth:

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Website: www.elizabethday.org

Elizabeth and Louise answer listener questions in our subscriber series, Failing with Friends. Join our community of subscribers here: https://lnk.to/7i0moR

Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: askhowtofail.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

Nish Kumar is one of the UK’s best-known comedians, known for his impassioned political progressiveness.

You might remember him as the host of the topical BBC comedy show, The Mash Report, which ran to great acclaim until it was abruptly cancelled in 2021 - one of his failures addresses this head-on. Kumar now co-hosts the popular podcast, Pod Save The UK and his 2026 tour, Angry Humour From A Really Nice Guy tackles the existential angst and political disquiet of a 40-year-old man.

We talk through his failed Edinburgh show, the fact he would never consume Huel, ‘the whole bread roll Mash Report thing’, his people pleasing tendencies, how his experiences of racism led to therapy and a PTSD diagnosis…and how his friendship with Ed Gamble has changed over the years. It’s not one to miss.

IN THIS EPISODE:

00:00 Intro

02:29 Immigrant Parents and Fear

04:41 Comedy Obsessed Teen

08:22 Nice Guy Angry Comic

11:31 Rage as Fuel

13:04 Edinburgh Show Failure

23:31 Bread Roll Fallout

27:20 Empathy and Comedy

27:53 The Bread Roll Incident

28:29 Clips, Context, and Backlash

29:49 Turning Failure into Material

31:24 Therapy and PTSD

34:28 Racism and Political Architecture

39:52 Progress, Parents and Politics

46:14 Friendship and Growing Up

💬 QUOTES TO REMEMBER:

Intellectual intelligence is useless without emotional intelligence

2013 was the most important year because I learnt everything about what I didn’t want to do in stand-up

My partner said I should seek therapy, but at the time that felt like an indulgence. I don’t feel that now.

🔗 LINKS + MENTIONS:

Nish Kumar is touring across the UK with Angry Humour from a Really Nice Guy until the end of November. Tickets are available from www.nishkumar.co.uk/gigs

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

Elizabeth’s Substack: www.theelizabethday.substack.com

📚 WANT MORE?

Stephen Merchant - swap.fm/l/Lta5mlFbVnPHyFb8R1n2

John Bishop - swap.fm/l/wRGKwuonJFQoujFlmDHI

💌 LOVE THIS EPISODE?

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👋 Follow How To Fail & Elizabeth:

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Website: www.elizabethday.org

Elizabeth and Nish answer listener questions in our subscriber series, Failing with Friends. Join our community of subscribers here: https://lnk.to/7i0moR

Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: askhowtofail.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

It was a privilege to have one of my all-time heroes, the feminist activist, writer and icon Gloria Steinem on How to Fail back in 2020 and we are heartbroken to hear of her passing at the age of 92. To celebrate her life, we’re re-releasing this very special episode.

We talked about her failure to understand her mother, her failure to be at her father's deathbed and her failure to learn lessons quickly enough - yes, we go deep... She also talked to me about how (then) at the age of 86, she is joyfully outliving society's expectations of her; of how fear can often be a sign of growth (let that sink in), about how 'anger is an energy cell', about how we are 'linked not ranked', about not having children, about spending a lifetime combatting misogyny and racism and sexism and injustice, and about the counteracting forces of love and compassion and friendship which keep her going.

Whoever said never meet your heroes clearly never met Gloria Steinem.

We love you Gloria Steinem, rest in power.

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]

Guest bookings for How To Fail only come from official @sonymusic.com emails

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

David Sedaris is one of America’s best-loved humorists, famous for turning the absurdities of everyday life into razor-sharp, deeply human essays. He joins Elizabeth Day on How to Fail to talk about the moments that have shaped him: from dropping out of university and ending up in his parents’ basement at 20, to being thrown out by his father and growing up with a parent who seemed to actively invest in his failure.

He talks candidly about heartbreak after a breakup at 32, the fear of being alone, grief at losing the people we love and his past crystal meth addiction and sobriety.

We also hear about the embarrassment of dropping out of Japanese school in Tokyo at 50…and the possibility of a cameo on The Archers.

IN THIS EPISODE:

00:00 Intro

03:39 How His Writing Evolved

04:27 Train Music Confrontation

07:03 Failure One: Dropping Out

10:38 A Father Rooting Against Him

13:16 Money Promises and Betrayal

18:03 Thrown Out and Self Worth

20:31 Friendship and Grief

23:22 Failure Two: Breakup at 32

27:38 Writing Love And Routine

28:46 Sharon The Practical Mom

33:08 Heartbreak Versus Grief

35:54 Crystal Meth And Fear

38:59 Conceptual Art On Fire

40:24 Tokyo Japanese School Quit

46:08 The Archers Cameo

💬 QUOTES TO REMEMBER:

“I just took every bit of advice [my father] ever gave me and did the opposite, and it was a really good strategy.”

“Fear kept me drinking. Fear kept me smoking. Fear kept me from leaving.”

“You’re never going to get what you want if you don’t work for it.”

“Every day is a new beginning.”

🔗 LINKS + MENTIONS:

The Land and Its People by David Sedaris is widely available across both online retailers and physical bookstores in the US and the UK.

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

Elizabeth’s Substack: www.theelizabethday.substack.com

📚 WANT MORE?

Dawn French - on fertility, friendship and being an anti-perfectionist http://swap.fm/l/NJDrzxLKhyi6icOrxmHT

Simon Cowell - on judgement, power and the uncomfortable responsibility of shaping someone’s future http://swap.fm/l/hSwuCNEuZNgnaG20v0yB

💌 LOVE THIS EPISODE?

Subscribe on Spotify, Apple or wherever you get your podcasts

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👋 Follow How To Fail & Elizabeth:

Instagram: @elizabday

TikTok: @howtofailpod

Podcast Instagram: @howtofailpod

Website: www.elizabethday.org

Elizabeth and David answer listener questions in our subscriber series, Failing with Friends. Join our community of subscribers here: https://lnk.to/7i0moR

Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: askhowtofail.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 episode with Mo Gawdat originally went out in 2019, but its message feels as relevant as ever. We’re re-releasing it to celebrate the 500th episode of How to Fail.

Just occasionally, you meet someone who changes the way you think about the world. That’s what happened when Elizabeth met Mo Gawdat, former Chief Business Officer at Google X, who spent years trying to solve a problem that seemed impossible to quantify: how can one individual be happy?

After 12 years of research, Gawdat developed an algorithm for happiness: happiness is greater than or equal to your perception of the events in your life, minus your expectations of how life should be. He wrote about it in his international bestseller Solve for Happy.

But that algorithm was put to the ultimate test when his beloved 21-year-old son, Ali, died in tragic circumstances. Mo joins me to talk about grief and depression, happiness as a form of fitness, coping with break-ups, the isolating effects of social media, why life is like a computer game, the illusion of time - and why we should always be polite to Siri.

IN THIS EPISODE:

00:00 Intro

03:23 Success Yet Depressed

06:14 Chasing Stuff for Joy

07:22 Engineering Happiness Reset

11:37 Six Modern Illusions

15:17 Happiness as Equation

20:35 Taming Your Inner Voice

28:51 Useful vs Joyful Thoughts

29:55 Grief Without Suffering

31:02 Ali Lived Reframing

32:47 Life as a Video Game

35:02 Halo Lessons on Purpose

40:13 Preventable Death and Resentment

45:09 Tech Promise and AI Risk

55:26 1 Billion Happy Mission

LINKS + MENTIONS:

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

Elizabeth’s Substack: www.theelizabethday.substack.com

WANT MORE?

Mo Gawdat’s episode from 2025 -

Dr Gabor Maté -

LOVE THIS EPISODE?

Subscribe on Spotify, Apple or wherever you get your podcasts

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Follow How To Fail & Elizabeth:

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TikTok: @howtofailpod

Podcast Instagram: @howtofailpod

Website: www.elizabethday.org

Guest bookings for How To Fail only come from official @sonymusic.com emails

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

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

To mark 500 episodes of How to Fail! To we’re re-releasing the first ever episode with Phoebe Waller Bridge, which originally went out in July 2018.

Phoebe Waller-Bridge, creator and star of Fleabag, writer of Killing Eve, superstar feminist and human embodiment of a Star Wars droid, joins How To Fail to talk about how she failed at her 20s (but got lots of brilliant material from the terrible dates she endured), failing at drama school, terrible auditions (including one for Downton Abbey) and how her female best friend is quite possibly the love of her life.

She also talks about emotional vulnerability, why women fail at anger and about finding glory in one’s mistakes. There’s a great exchange about whether women should be open about whether or not they want children and a whole segue into the desirability of alabaster foreheads. Oh, and we cover the time Phoebe met Meryl Streep and embarrassed herself horribly, in what might be one of the greatest celebrity anecdotes of all time involving apple crumble.

IN THIS EPISODE:

00:00 Introduction

02:04 Sudden Fame Reality

04:33 RADA And Early Rejection

07:50 Emotional Acting Truth

08:41 Love Life Failures

13:14 Fleabag And Female Voice

18:05 Auditions Power And Ambition

25:37 Creative Lifeline Friendship

26:21 How They Met Vicky

27:40 Muses Not Mistresses

29:15 Women And Anger

30:55 Female Killers Fascination

33:20 The Babies Question

40:54 Feminism And Body Image

44:40 Celebrity Encounters Finale

LINKS + MENTIONS:

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

Elizabeth’s Substack: www.theelizabethday.substack.com

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