Podcast Summary: How To Fail With Elizabeth Day

Episode: ON MOTHERHOOD… with Jessie Ware and Francesca Segal
Date: March 16, 2026
Host: Elizabeth Day
Guests: Jessie Ware (singer-songwriter), Francesca Segal (author)

Overview

This episode of How To Fail explores the complex, messy, and contradictory realities of motherhood—well beyond the rose-tinted images often portrayed. Host Elizabeth Day is joined by singer Jessie Ware and writer Francesca Segal, both of whom open up about their very different but equally powerful experiences. They discuss the pressures of perfection, the unexpected failures, the shame and solidarity of NICU life, and the personal growth that emerges from honest self-reflection and vulnerability.

Key Discussion Points & Insights

1. Jessie Ware on Motherhood, Work, and Self-Expectation

(03:32–11:00)

• Proving Herself to the World (and to Herself)

  • Jessie describes the intense pressure she felt to "do it all" as a new working mother, especially within a "rather sexist, ageist industry."
  • She looks back with some regret at her determination to appear perfect, admitting, "I was really struggling to pretend that everything was okay and actually tried to prove to a rather sexist ageist industry that you can have it all. And I don't think I needed to do that. And I regret that." (04:46)
  • On her return to work, she juggled being present for her daughter with recording sessions, touring, and domestic responsibilities, often feeling emotionally exhausted and overwhelmed.

• Learning to Be Kinder to Herself

  • Jessie reflects: “I just kind of wish I’d been a bit kinder to myself and maybe lived in the present a bit more and taken that maternity leave… I regret that a lot.” (05:30)
  • With her second child, she felt more in control, but still struggled with multitasking and being truly present.

• Being in the Present vs. Fear of Missing Out

  • Discussion ensues about the irony of wanting "to make the most of the present" but constantly overfilling one's diary out of fear “that I’m not always going to have these chances.” (Elizabeth Day, 07:18)
  • Jessie confesses: “I think failure to live in the present happened with me not enjoying that initial period of being a new artist… I was always like fearful of what was going to happen next or that it would be taken away.” (06:35)

• The Power of Saying No

  • Both guests discuss the liberation and power found in learning to say “no,” with Jessie noting it’s “the most powerful thing I could ever do and the most fulfilling.” (07:24)

• Gaining Confidence Through the Podcast

  • Jessie credits her own podcast as a newfound source of confidence beyond her music career: “Weirdly, it kind of was all come back round... just having this other job where I just feel safer.” (07:57)

• Honesty and Vulnerability Resonating Most

  • Elizabeth notes: “The biggest lesson... was that people responded most to me when I was being most honest and vulnerable.” (08:32)

• Strategies for Presence (and Failing at Meditation)

  • Both Jessie and Elizabeth joke about having paid for the Headspace app but feeling stressed by the reminders, not soothed.
    • “Oh, my God, I fucking paid for that headspace.” (Jessie Ware, 09:16)
    • “Two fucking times.” (Jessie Ware, 09:19)
    • “I got stressed then about meditating.” (Elizabeth Day, 09:22)
  • Jessie finds cooking to be her main avenue for switching off and being present, even if chaotic: “My favorite thing is having the kids in the kitchen whilst I'm cooking. I can watch them, I'm cooking, they're doing. So everyone's happy.” (09:34)

2. Francesca Segal on Premature Birth and NICU Realities

(13:20–21:37)

• Failure of the Motherhood Narrative

  • Francesca’s twins were born prematurely, shattering her expectations of an "ideal" beginning.
  • She critiques the pervasive narrative around immediate skin-to-skin, early bonding, and the rush of maternal love: "For an awful lot of women... those early moments aren't possible and they are so cherished in this narrative we have of what's owed to these babies that you immediately feel like you have damaged your children in some way." (Francesca Segal, 13:44)

• Complex Emotions in the NICU

  • On not meeting or holding her babies right away: “There was just a sort of big soup of hormones and worry, terror and love and fear and guilt, enormous amounts of guilt that we'd sort of found ourselves there... I was left free to construct narratives in which it was always my fault.” (15:13)

• Names and Superstition

  • The twins were referred to as “twin one and twin two” by the hospital, then affectionately as “Ayla and Bela” by the parents, highlighting the surreal detachment and focus on survival over ceremony. (15:53)

• NICU Solidarity and the Mirror Story

  • Francesca poignantly describes her first experience holding her daughter in the NICU, unable to see her under the wires—until another mother’s husband brings a hand mirror.
    • “One of the other mothers... sent her husband over and gave me a hand mirror. And that's how you look at your baby's face when you're holding a premature baby on your chest.” (16:33)
  • Elizabeth highlights the deep solidarity: “It’s such a beautiful moment of solidarity between two women in a traumatic and similar situation that you can’t possibly understand unless you’ve been through it.” (17:43)

• Building Community in Dire Circumstances

  • Francesca reflects on the “milking shed” where mothers shared breast pumps and stories:
    • “We were in what we call the milking shed endlessly... and that was really where these incredible friendships began. Also just really powerful human encounters that might only last an hour... you would talk incredibly frankly.” (18:37)
  • The atmosphere was one of support, not comparison.

3. Transformation Through Adversity

(20:03–21:37)

• Finding Her Voice as a Mother
  • Francesca describes how she did not instantly become a mother, but learned by observing others:
    • “I did not become a mother the moment my children were lifted from me. I had to learn. And I was slow and I learned by study, careful, rational study of other people around me.” (20:33)
  • Witnessing other mothers advocate for their children taught her: “The NHS is incredible... but the only person who’s there every day is you.”

Notable Quotes & Memorable Moments

• Jessie Ware:

  • “I was really struggling to pretend that everything was okay and actually tried to prove to a rather sexist ageist industry that you can have it all. And I don’t think I needed to do that. And I regret that.” (04:46)
  • “I do try and do too many things. And I think failure to live in the present happened with me not enjoying that initial period of being a new artist.” (06:35)
  • “Oh, my god, I fucking paid for that headspace.” (09:16)
  • “My phone is my biggest enemy... I could be glued to it all day, working. I could always find time to fit in another email.” (10:46)

• Elizabeth Day:

  • "Ironically, it's that I want to make the most of the present [that] prevents me from living in the present." (07:21)
  • “People responded most to me when I was being most honest and vulnerable.” (08:32)

• Francesca Segal:

  • “For an awful lot of women... those early moments aren't possible and they are so cherished in this narrative we have of what's owed to these babies that you immediately feel like you have damaged your children in some way.” (13:44)
  • “The first time I held one of them... another mother sent her husband over and gave me a hand mirror. That’s how you look at your baby's face when you're holding a premature baby on your chest.” (16:33)
  • “I did not become a mother the moment my children were sort of lifted from me. I had to learn. And I was slow and I learned by study, careful, rational study of other people around me.” (20:33)

Timestamps for Major Segments

• 03:32–11:00: Jessie Ware on motherhood, work, and finding presence
• 13:20–21:37: Francesca Segal on premature birth, NICU experience, solidarity with other mothers, and identity transformation

Tone & Atmosphere

The episode is raw, self-deprecating, and warm, with speakers willing to laugh at themselves (and swear freely) while exploring difficult truths. Both guests emphasize honesty and vulnerability, inviting listeners to discard perfection and embrace the solidarity found in shared struggle.

This conversation provides comfort—and practical wisdom—for mothers and anyone who has struggled with letting go of self-imposed ideals. It’s a reminder that you are never alone and that “a fail shared is a fail halved.”