The Diary of a CEOElizabeth Day Opens Up About Heartbreak, Miscarriage & Failure | E77
CHAPTERS
- 0:00 – 3:35
Introduction: Success, Vulnerability, and the Weight of Expectations
Steven introduces Elizabeth Day, praising her intellect, warmth, and willingness to be vulnerable. He frames the discussion around how societal expectations of success and failure can deeply damage our happiness and self-concept.
- •Steven struggles to play devil’s advocate because he agrees with so many of Day’s views.
- •He highlights how powerful it is when public figures openly discuss trauma, failure, and vulnerability.
- •The episode’s premise: social expectations of what life ‘should’ look like can profoundly ‘fuck you up’.
- 3:35 – 9:00
Defining Failure and Questioning the ‘Plan’
Day offers her definition of failure and interrogates where our life plans actually come from. She shares how patriarchy, 80s rom-coms, and gender conditioning led her to pursue marriage and motherhood as default goals, and how not achieving them left her feeling like a failure.
- •Failure defined as life not going according to plan.
- •Key question: is the plan genuinely yours or culturally inherited?
- •Day’s 30s: marriage to the wrong person, divorce, failed fertility treatments, miscarriage.
- •Reframing: after grief, she felt strength and liberation in having no fixed plan.
- •Realization that feeling like a failure was largely socially conditioned.
- 9:00 – 17:20
External Validation, Self-Worth, and a Smaller ‘Context’
They explore how early conditioning around achievement and appearance shaped their definitions of success. Day describes basing her worth on academic success and external approval; Bartlett shares his childhood belief that becoming a ‘happy, sexy millionaire’ would fix everything.
- •Day’s upbringing was rich in books and cultural conversation but still steeped in gender stereotypes.
- •Academic success became her main route to approval and a proxy for self-worth.
- •She eventually realizes meaningful validation can only come from herself and a small group of close relationships.
- •Bartlett argues for shrinking your comparison ‘context’ by curating social media and focusing on a tight, healthy circle.
- 17:20 – 35:50
Social Media, Criticism, and Protecting Your Mental Space
Day candidly describes how online criticism can derail her emotionally, even when she knows rationally it shouldn’t. She and Bartlett trade tactics for using social media consciously rather than being used by it, including muting, time boundaries, and reframing critical comments.
- •Example: a socially distanced walk photo leads to accusations of irresponsibility, triggering guilt and anxiety.
- •Another example: critics accuse her of ‘exploiting failure’ for success and infertility for a career.
- •Her coping methods: wait 24 hours before responding, lean on offline support, ask what pain the critic might be in.
- •Strategic response: she publicly refuted a particularly harmful newspaper line about ‘exploiting infertility’ and received broad support.
- •Bartlett’s tactics: turn off notifications, mute viral tweets, and treat social media use as a conscious choice.
- 35:50 – 43:40
People-Pleasing, Work Exploitation, and Finding Your Voice
Day unpacks her history as a hardcore people-pleaser in relationships and at work. She shows how constantly saying yes made her easy to exploit and prevented her from ever expressing who she really was, contributing to the breakdown of her marriage and stagnation in her career.
- •Raised to be ‘pleasant and pliable,’ she tied worth to keeping others happy.
- •From age 19 to 36 she was almost never single, always molding herself to partners’ needs.
- •At work, she never said no, took undesirable assignments, and never asked for a pay rise.
- •Insight: extreme people-pleasing is ultimately selfish because you never give people the real you.
- •Realizing that not using her voice, avoiding conflict, and internalizing resentment contributed to her marriage ending.
- 43:40 – 58:30
Relationships, Communication, and Love Languages with a CEO Partner
The conversation shifts to how to maintain relationships when one person is a driven founder/CEO. Day uses her marriage to illustrate how different communication preferences and love languages can be reconciled, given honesty, feedback, and emotional clarity.
- •Bartlett admits struggling in relationships due to time scarcity, selfishness, and an uncompromising work mode.
- •Day’s husband, a CEO, once said, “I never do anything I don’t want to do,” which she initially read as selfish but now reads as radical honesty.
- •They negotiated texting vs calling; he sees texts as ‘cheap’ communication, she loves them.
- •Love languages: he is ‘acts of service’ and ‘touch’; she is ‘words of affirmation’ and, increasingly, ‘quality time.’
- •She values that he takes feedback in a practical, non-defensive way, and returns later with a considered action plan.
- 58:30 – 1:04:00
Loneliness, Lockdown, and Rethinking Social Circles
Day discusses her longstanding fear of being lonely at the end of life—and how the pandemic unexpectedly eased it. With her diary wiped clean, she realized she hadn’t truly wanted many of her social engagements and learned she’s more resilient and introverted than she thought.
- •Lockdown revealed she’d been saying yes to social obligations she didn’t want.
- •Her ‘nucleus’ of truly important people is very small, and that’s enough.
- •She identifies as an introvert who has learned to perform extroversion in public life.
- •Shrinking her world showed her she can handle a much smaller, quieter life without being destroyed by loneliness.
- 1:04:00 – 1:13:30
Confidence, ‘Enoughness,’ and Rethinking Ambition
They tackle the paradox of self-worth and ambition: can you feel ‘enough’ and still be driven? Bartlett argues that ‘enough’ is a linguistic trap and that real ambition arises once you stop trying to prove your worth to others.
- •Day feels confident in what she does (writing, podcasting, conversation) but still struggles with feeling inherently ‘enough.’
- •Bartlett dismantles the ‘enough’ concept: you don’t become less or more as a person; that’s an external comparison construct.
- •External ‘not enough’ beliefs fuel shallow ambitions (e.g., Lamborghinis); intrinsic security leads to authentic ambitions (books, piano, meaningful work).
- •Reframing: knowing you are already ‘enough’ lets you pursue goals for your reasons, not to fix an internal deficit.
- 1:13:30 – 1:23:40
Thoughts, Grief, and Training the Anxious Brain
Drawing on Mo Gawdat’s ideas, Day separates the self from the anxious brain and illustrates cognitive reframing using a powerful story about his son’s death. They discuss learning to observe and edit thoughts rather than being ruled by them, and how exercise helps.
- •Mo Gawdat teaches that thoughts are a product of the brain like blood from the heart; they are not the self.
- •His reframing of “Ali died” to “Ali died, but he also lived” shows how adding meaning can shift unbearable grief.
- •Day emphasizes we can’t equate catastrophic events (death, illness, pandemic) with minor failures like a driving test.
- •The aim is to mourn without being permanently defined by a single painful event.
- •Exercise and movement help both hosts get out of their heads, process emotions, and generate creative ideas.
- 1:23:40 – 1:34:30
Failosophy Principles: Twenties, Breakups, and Personal Responsibility
Day walks through key principles from her book ‘Failosophy,’ including why many feel they’ve failed in their 20s and how to reframe breakups. They also discuss personal responsibility in contexts shaped by privilege, inequality, and systemic barriers.
- •Twenties often feel like failure due to lost structure, comparison culture, and pressure to ‘find your passion’ while paying rent and building identity.
- •She insists most people are still grinding spices in the pestle and mortar of life in that decade; clarity usually comes later.
- •Breakups aren’t inherently tragedies; each ‘failed’ relationship teaches something and isn’t a failure just because it ended.
- •She likes the mantra ‘rejection is protection’ to help people survive early heartbreak, followed by honest self-audit later.
- •Day explicitly acknowledges her own white, middle-class privilege and the unequal distribution of chances to fail and recover.
- 1:34:30 – 1:44:50
Nuance, Cancel Culture, and Speaking on Race and Power
The discussion widens into how polarized online cultures pressure people to adopt simplistic positions on complex issues like Black Lives Matter. Bartlett argues for nuance and free thought, criticizing virtue signaling and the fragility of online discourse, while Day probes her responsibilities as a white ally.
- •Day felt conflicted about how to respond publicly to George Floyd’s murder and BLM, wondering what was genuinely helpful.
- •Bartlett defends the right not to post performative content immediately, emphasizing people process trauma differently.
- •He critiques virtue signaling (e.g., black squares) without deeper, systemic change or education.
- •They note how algorithms amplify groupthink and penalize nuance, fueling cancel culture and self-censorship.
- •Day points out women—and especially successful women—are challenged more when sharing personal experience than men are.
- 1:44:50
Vulnerability, Oversharing, and the Power of Telling the Truth
In the final section, they return to Day’s core thesis: that sharing our vulnerabilities is how we forge deep human connection. She explains the difference between healthy vulnerability and oversharing, touches on fertility grief and boundaries, and reflects on why she still won’t publicize a future pregnancy.
- •Day’s most impactful work has come from talking about infertility, miscarriage, and divorce—topics loaded with shame for many.
- •Vulnerability is letting the mask slip; oversharing is about timing, audience, and boundaries.
- •She recommends first sharing raw pain in safe spaces before speaking publicly, because not everyone can be trusted with your story.
- •She wouldn’t publicly announce a pregnancy due to empathy for women still struggling and her own anxiety from past loss.
- •She argues women are often accused of ‘oversharing’ as a way to shame them back into silence.
- •The episode closes with mutual appreciation: Steven thanks her for her radical honesty; she credits him with creating a space where she can be fully herself and notes his unusual wisdom for his age.
