TThe Diary of a CEO
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19 April 2021

Elizabeth Day Opens Up About Heartbreak, Miscarriage & Failure

6Frameworks
13Insights

Frameworks in this episode

Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Myth Buster· 2

Myth Buster43:00

Why Day and Bartlett Distrust Questions About Soulmates and Passion

Day and Bartlett argue that familiar questions can smuggle in assumptions before anyone answers them. They use soulmates and finding a passion as examples: the wording may imply incompleteness, a single correct person or pursuit, and failure if it has not yet been found.

  • A soulmate question may imply that a person is incomplete alone
  • Finding a passion may imply one hidden pursuit that must be discovered
  • Day says intense passion can feel chaotic rather than safe
  • Both prefer examining a question's assumptions before accepting its frame

question the question

Steven Bartlett · 44:00

I want to feel safe and known that for me is like true romance

Elizabeth Day · 44:30
#questions#soulmates#passion#assumptions
Myth Buster54:00

Day's Caveat: Some Losses Cannot Be Turned Quickly Into Lessons

Day identifies a limit in her broad definition of failure: illness, bereavement, a pandemic, and other cataclysmic events are not comparable to an ordinary failed test. She says such losses require mourning and coming to terms with what is gone, while describing meaning-making as her chosen response rather than an easy or compulsory formula.

  • Day calls this a flaw in an otherwise broad failure definition
  • She rejects treating catastrophic loss like a routine setback
  • Mourning is presented as appropriate and necessary
  • She distinguishes continuing sadness from repeatedly living inside the pain
  • Her preference for later meaning is framed as a personal way of living

those kind of failures will require a process of mourning and coming to terms with the thing that you've lost

Elizabeth Day · 54:30

that's how I choose to live my life because that makes it less sad

Elizabeth Day · 55:00
#grief#loss#failure#mourning

Hot Take· 2

Hot Take40:00

Bartlett's Claim: Feeling Enough Can Improve Ambition

Bartlett argues that treating human worth as something that rises and falls with comparison drives externally chosen ambitions. His stated conclusion is that a stable sense of intrinsic worth can redirect effort toward goals a person genuinely values; Day strongly agrees, but the episode offers this as their view rather than an established psychological finding.

  • Bartlett questions whether intrinsic human worth can become more or less
  • He links inadequacy driven by comparison to status goals he did not genuinely value
  • He says accepting stable worth redirected him toward writing and learning piano
  • The transcript presents the argument as Bartlett's personal conclusion

once I knew I was enough I then went after things

Steven Bartlett · 42:00

real ambition is for you it's chasing what you want for your reasons

Steven Bartlett · 42:30
#ambition#enoughness#status#self-worth
Hot Take1:00:00

Bartlett Rejects Binary Tests of Social-Media Activism

In a discussion prompted by George Floyd's killing and Black Lives Matter posts, Bartlett argues that silence on a platform does not establish indifference and that people process traumatic events differently. He criticises symbolic posting when it substitutes for sustained education or systemic action; these are Bartlett's claims and judgments, not established measures of another person's motives.

  • Bartlett says he did not post for several days after seeing the footage because he did not want to revisit it
  • He rejects forcing every response into one approved public format
  • He values longer-term education and systemic action over a single symbolic post
  • Day agrees that compassion and nuance fit poorly into binary social-media dynamics
  • The episode does not establish a reliable way to infer private commitment from posting behaviour

people process things in their own ways and that's normal

Steven Bartlett · 1:02:00

compassion and nuance can't be fitted into the binary world of social media

Elizabeth Day · 1:03:30
#social media#black lives matter#activism#nuance

Explainer· 1

Explainer21:30

How People-Pleasing Can Become Self-Erasure

Day says she once based her worth on keeping partners and colleagues happy, accepting unwanted work and avoiding complaints. In her account, extreme people-pleasing did not simply make her generous; it hid her preferences, made her exploitable at work, and prevented partners from knowing her fully.

  • Day moved rapidly between long-term relationships because partnership supplied identity
  • At work she repeatedly accepted overtime and unwanted commissions
  • Making herself indispensable did not produce the advancement she expected
  • Conflict avoidance left her presenting a perfected version rather than her full self

you just become an easily exploitable asset

Elizabeth Day · 23:00

you're giving a version of perfection to someone that is never fully real

Elizabeth Day · 24:00
#people pleasing#boundaries#work#relationships

Story· 3

Story30:30

What a Love-Languages Quiz Revealed About Day's Relationship

Day describes using a love-languages quiz as a conversation aid after discovering that she and her husband attached different meanings to texting, calls, touch, affirmation, and shared time. She says her own stated preference also changed as the relationship became safer, suggesting that expressed needs can reflect current circumstances rather than a fixed identity.

  • Day valued written contact while her husband saw calls and time together as more meaningful
  • The quiz surfaced his preference for acts of service and touch
  • Day initially chose words of affirmation after relationships in which she felt unsafe
  • She later found quality time more important in a secure relationship

I think that's about having different love languages

Elizabeth Day · 31:30

now actually in my relationship I feel really safe so for me it is quality time

Elizabeth Day · 32:30
#love languages#relationships#communication#safety
Story35:30

Lockdown Revealed How Small Day's Real Social Nucleus Was

When the pandemic emptied her diary, Day realised that many social commitments had come from obligation and fear of offending people. She found that a very small nucleus of close relationships was enough, and that she had been neglecting generous friendships while spending more effort on less secure ones.

  • An empty diary exposed how many invitations Day had accepted from obligation
  • She says her core group is very small
  • Secure friendships needed less constant maintenance to remain welcoming
  • The experience reduced her fear of loneliness

I didn't really want to see the majority of people that I was going to see

Elizabeth Day · 36:30

my core my nucleus of people is very very small

Elizabeth Day · 36:30
#loneliness#friendship#lockdown#introversion
Story1:24:30

Why Day Would Keep a Future Pregnancy Private

Day says she remains determined to become a mother but would not share a future pregnancy publicly because she expects fear and anxiety and remembers the pain of seeing others' parenthood while experiencing fertility treatment and miscarriage. She frames curating her feed as her own responsibility and does not blame parents for discussing the difficulties of homeschooling.

  • Day describes yearning and envy as reactions to an experience she has not had
  • She says miscarriage during lockdown and delayed fertility treatment made parenting posts painful
  • She explicitly says parents are not to blame for her reaction
  • Her proposed boundary is personal restraint around her own future announcement
  • The segment reflects Day's experience and does not make a medical claim about fertility or miscarriage

I am still determined to be a mother

Elizabeth Day · 1:24:30

I take personal responsibility for my reaction and that's where I need to curate my social media feed

Elizabeth Day · 1:26:30
#fertility#miscarriage#pregnancy#social media

Q&A· 1

Q&A38:00

Day Feels Confident in Her Craft, Not in Every Part of Herself

Day distinguishes confidence in specific practised abilities from a global sense of self-worth. She says she trusts her writing, podcasting, and ability to connect, while still struggling at times with feeling that she is enough.

  • Day names writing and podcasting as areas of earned confidence
  • She values one-to-one connection more than performing socially in a crowd
  • Competence in visible work does not erase her private self-worth struggle
  • Her account resists treating confidence as one fixed personality trait

I'm confident that I can write I'm now confident that I can podcast

Elizabeth Day · 38:30

I'm not hugely confident about myself in the sense that I still struggle with self-worth

Elizabeth Day · 39:00
#confidence#self-worth#craft#introversion

Takeaway· 4

Takeaway07:30

When Achievement Became a Substitute for Self-Worth

Day says academic success brought approval, which trained her to pursue ever more achievement in the hope of finally feeling worthwhile. She now limits meaningful external validation to a small group of cornerstone relationships and tries to ground the rest within herself.

  • Doing well in exams brought Day approval
  • She describes a loop of trying to earn worth through better performance
  • Outsourcing self-worth made other people's opinions disproportionately powerful
  • She now gives greatest weight to her own view and a few close relationships

when I did well on an exam I got approval and that for me became a substitute for self-worth

Elizabeth Day · 08:00

I was outsourcing my sense of self to everyone else's opinions of me

Elizabeth Day · 08:30
#self-worth#achievement#validation#success
Takeaway48:00

Why Day Treats Walking and Looking Around as Part of Writing

Day says useful writing does not consist only of time spent typing. Walking, exercising, observing people, and letting the mind rest can create a fallow period in which experiences feed later ideas; she offers this as a writing practice from her experience, not a universal productivity law.

  • Exercise helps Day feel embodied and less trapped in thought
  • She sometimes processes a problem while appearing not to think about it
  • Observation and rest can later contribute to inspiration
  • She advises writers not to feel guilty whenever they are away from the page

don't feel guilty for not actually doing the writing sometimes

Elizabeth Day · 49:00

your brain needs rest but it also needs like a creative fallow period

Elizabeth Day · 49:30
#writing#creativity#walking#exercise
Takeaway55:30

Day Says Acknowledging Privilege Does Not Cancel Hard Work

Day says personal responsibility matters while opportunities to fail are distributed unequally by class, race, and other social structures. She describes moving from hearing privilege criticism as an attack to accepting that substantial advantages and genuine hard work can both be facts, then questions why women are often pressed to display hardship before speaking with authority.

  • Day acknowledges receiving many opportunities to fail
  • She says advantage and hard work are not mutually exclusive
  • A memoir can only speak honestly from its author's lived experience
  • She believes women face more pressure than men to justify the right to give advice

I have had massive advantages in my life and that's a fact as is the fact that I've worked hard as well

Elizabeth Day · 58:00

women are more often challenged for talking about their personal experiences than men are

Elizabeth Day · 58:30
#privilege#responsibility#gender#opportunity
Takeaway1:08:00

Why Day Treats the Twenties as a Transition, Not a Final Score

Day argues that many people feel they failed in their twenties because education's clear exam-and-reward structure disappears just as work, rent, identity, relationships, and online comparison intensify. From her experience, later decades brought greater self-knowledge and more opportunities, so she rejects the expectation that adulthood should already be solved by 30.

  • Social media encourages comparison with curated appearances
  • Leaving education removes a familiar measure of progress
  • Career, housing, identity, and relationship pressures arrive together
  • Day sees the decade as one of transition and discovery
  • She reports receiving more opportunities after her twenties

there is no exam that you can sit to show that you're being a good grown-up

Elizabeth Day · 1:09:00

your twenties are a decade of transition of discovering who you are

Elizabeth Day · 1:10:00
#twenties#comparison#adulthood#identity