How To Fail With Elizabeth Day

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

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👋 Follow How To Fail & Elizabeth:

Instagram: @elizabday

TikTok: @howtofailpod

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 podcastadsales@sonymusic.com

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?

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 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 podcastadsales@sonymusic.com

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?

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 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 podcastadsales@sonymusic.com

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 podcastadsales@sonymusic.com

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

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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

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 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 podcastadsales@sonymusic.com

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