The Diary of a CEOJessie J: I Quit Music, Deleted An Album, Then Changed My Mind | E139
CHAPTERS
- 4:00 – 10:40
Roots, Family Energy, And Learning To Feel
Jessie describes her modest but emotionally rich upbringing, with parents who created experiences from very little and refused to define her by illness. Her father’s work in mental health and his ability to balance tears with laughter shaped how she processes pain publicly and uses humor as a connective, healing tool.
- •Grew up without wealth but with a strong focus on energy, experiences, and feeling over “things.”
- •Parents turned small moments (camping in the garden, dad pretending to be a bear) into cherished memories.
- •Spent significant time in hospital as a child but was never treated as “sick,” which stopped illness defining her.
- •Father, a mental‑health social worker, modeled emotional openness, using humor to safely access and release pain.
- •Jessie now uses the same pattern on stage: allowing deep sadness, then breaking tension with laughter so people feel less alone.
- 10:40 – 17:00
Childhood Illness, Stroke At 17, And The Birth Of An Empath
She recounts collapsing in Epping Forest, being diagnosed with a serious heart rhythm issue, and enduring heavy medication and operations. A powerful encounter with a dying boy in the hospital inspired her first song, 'Big White Room', and ongoing health scares—including a stroke at 17—taught her to see pain as a teacher rather than an identity.
- •Collapsed racing her dad in Epping Forest; diagnosed with a heart condition (WPW runs in her family).
- •Experienced seizures, blackouts, and multiple hospital stays, culminating in an unsuccessful ablation procedure.
- •Witnessed a young boy pray not to die; he passed overnight, sparking years‑long reflection and the song 'Big White Room'.
- •Had a stroke at 17 while working in Hamleys, losing feeling on her right side for almost a month.
- •Refuses to lead with her illnesses; believes these experiences kept her grounded, away from self‑destruction, and focused on health.
- 17:00 – 28:40
Health As Warning System And Career Disruptions
Jessie traces how major career milestones repeatedly collided with health crises—broken foot just as she was about to break America, losing her singing voice before an album, going deaf in one ear. She’s reinterpreted these as protective interventions from her body, prompting her to question what she’s ignoring each time and to reconsider projects, including an entire unreleased album.
- •Pattern of major health events coinciding with big breaks (e.g., broken foot before Katy Perry tour, throat/nerve damage before album rollout).
- •Went deaf in one ear due to Meniere’s; saw it as a signal rather than random misfortune.
- •Queries, “What am I not listening to?” whenever her body crashes.
- •Recently recovered her voice, planned a residency, then had a miscarriage the day before first show—and still performed.
- •Now sees these interruptions as alignment checks, not punishment.
- 28:40 – 35:40
Endometriosis, Adenomyosis, And Redefining Womanhood
She details years of misdiagnosed agony dismissed as IBS before finally learning she had endometriosis and adenomyosis. Faced with the choice of a hysterectomy at 26 or lifelong pain management, she chose to keep her uterus, overhaul her lifestyle, and accept uncertainty around fertility, which later framed her miscarriage experience.
- •Extreme pelvic pain was repeatedly misdiagnosed as IBS; she persisted until getting an endometriosis diagnosis.
- •Second surgery revealed adenomyosis—uterine wall cells that can’t be removed without removing the uterus.
- •Doctor recommended a hysterectomy in her mid‑20s; she refused and opted to manage pain and change lifestyle instead.
- •Went plant‑based, slowed her career pace after the Bang Bang/Sweet Talker era, and wrote The Rose album during this recalibration.
- •This diagnosis and choice set up later fertility challenges and expectations around pregnancy.
- 35:40 – 46:40
Fame, Anxiety, And Losing The Ability To Live Unconsciously
At the height of her visibility in the UK and Australia, Jessie developed debilitating anxiety tied to being constantly watched and critiqued. She describes feeling trapped in hotels, paranoid about cameras at petrol stations or the beach, absorbing hurtful comments about her appearance and mannerisms, and briefly becoming the ‘diva’ the media portrayed her as out of exhaustion.
- •2014–2016 marked her lowest point emotionally in the industry despite career success.
- •Felt under constant surveillance; feared being filmed eating, in swimwear, or saying no to photos.
- •Hyper‑aware of online criticism about her jaw, cellulite, speech patterns, and outfits.
- •Became anxious even doing mundane tasks, like filling her car with petrol, due to imagined judgment.
- •At times leaned into the negative media caricature because fighting it felt futile.
- •Eventually asked loved ones to stop sending her press links and comments, focusing on protecting her mindset instead.
- 46:40 – 58:40
Brand vs. Self, Stepping Off The Hamster Wheel, And Management Struggles
Jessie explains how the Jessie J persona swallowed Jessica: catsuits at family barbecues, full glam for casual dinners, and no sense of who she was off stage. Although her label has often supported her creatively, she has repeatedly struggled to find management that matches her passion and breadth, leading to six manager changes and a renewed resolve to demand better alignment.
- •Admits she became her stage persona 24/7, unsure how to “tone it down” or what she even liked personally.
- •Recognized she didn’t know her hobbies, favorite foods, or colors outside work; took four years to “disappear” and reset after her third album.
- •Contrasts her label’s relative support (especially for The Rose) with lack of passion and vision from internal management teams.
- •Recently parted ways with her sixth manager, acknowledging she must examine her own patterns in choosing the wrong people.
- •Wants managers who love music, challenge her, bring ideas, and reflect the diversity and inclusivity she wants in her audience.
- •Uses the metaphor of her career as a shop “selling ladders outside but roses inside” to describe public misalignment with her true artistry.
- 58:40 – 1:07:20
Quitting Music, Rediscovering Writing, And The Rose Album
Burnt out after a third album that didn’t represent her, multiple losses, and a major breakup, Jessie told her label she wanted out of music. A makeup campaign unexpectedly led her back into the studio, where a chance beat rekindled her songwriting instinct and birthed 'Think About That' and The Rose album, a body of work she considers her most authentic despite limited commercial push.
- •In 2016, emotionally exhausted, she asked her label to drop her and planned to step away from music.
- •Took a makeup campaign mainly for income and insisted on doing a cover to avoid new‑music expectations.
- •Producer Camper played her a beat; she reluctantly listened, immediately wrote 'Think About That', and realized she couldn’t stop writing.
- •The Rose album emerged from this period, focusing on raw, darker emotions she’d previously sidelined for upbeat hits.
- •She fired managers mid‑tour, recognizing that even during creative rebirth, her support system was misaligned.
- 1:07:20 – 1:16:20
Pandemic Reflection, Shelving An Album, And Letting Grief Live
The pandemic forced Jessie to mellow, drop some perfectionist rituals, cook, and write an album that now doesn’t feel right to release. Recent grief—miscarriage and Jamal Edwards’ death—has made her acutely aware of unresolved sorrow, which now surfaces freely in tears and art and is reshaping what kind of music she wants to make.
- •Lockdown exposed how much time she wasted on over‑preparation and rigid routines.
- •Wrote a full album in that period but now feels it sounds like something several other artists could make.
- •Says she can’t “see” the audience for those songs; wants to create work only she could deliver.
- •Grief feels “present and living,” coming out through tears and songwriting.
- •Losing Jamal and others reframed career ambitions; she now prioritizes truth and emotional resonance over sonic trends.
- 1:16:20 – 1:28:40
Jamal Edwards, Dave, And The Weight Of Compounded Loss
Jessie talks through the deaths of entrepreneur Jamal Edwards and her longtime security guard, Dave, both of whom embodied vital emotional roles for her: self‑belief and safety. She explores how uniquely intimate shared experiences with them make grieving isolating, and how their absence forces her to internalize the qualities they once provided.
- •Jamal championed her from age 17 and was living proof she could succeed; he always talked himself into rooms to promote others.
- •His death felt profoundly unfair given his generosity and appetite for life; she credits him with giving her courage to make tough career decisions now.
- •Dave, her bodyguard, was with her daily for years—waking her, closing the hotel door at night, holding her hand through turbulence.
- •They shared private rituals (post‑show walks, whale‑spotting in Australia, in‑jokes like shouting “Whale!” to exit awkward situations).
- •She laments that he may never have known how special he was to her and wishes she could have protected him from himself.
- •Realizes her current work is learning to feel safe and self‑confident without outsourcing those needs to others.
- 1:28:40 – 1:44:40
Miscarriage, Radical Openness, And The Loneliness Of Private Pain
Jessie gives a raw, detailed account of discovering her baby’s heartbeat was weak, then gone within hours, while alone in Los Angeles. Pressured to decide about a show the next day, she posted about the loss publicly partly because she had no one physically to break on. The hardest moment was returning home after the show to an empty house, grieving the imagined life as much as the baby itself.
- •Had been told sustaining pregnancy might be difficult; found herself joyfully, secretly pregnant and very sick.
- •Initial scan showed a very weak heartbeat and possible deformity; a stranger on the street told her this would help others someday.
- •Second opinion hours later confirmed no heartbeat; she immediately faced questions about whether to proceed with a scheduled show.
- •Chose to perform, posting about the miscarriage beforehand because she lacked loved ones physically present to support her.
- •Describes falling to her knees upon returning home alone as the loneliest moment of her life.
- •Says she was grieving not only the baby but the entire future she had already envisioned.
- •Ultimately believes the loss showed her she wasn’t meant to do motherhood alone and has deepened her self‑love and empathy for others who’ve endured repeated losses.
- 1:44:40 – 1:52:40
Love, Privacy, And Navigating Relationships Under The Spotlight
Reflecting on past public and semi‑public relationships, Jessie explains why she now fiercely guards her romantic life. Fame can prematurely define and distort relationships that are still forming, and media narratives often force her to post simply to regain control. Despite that, she admits she’s been “properly in love” once—recently—and is learning to balance openness with protection.
- •Her autobiography originally had a big chapter on love that she cut to preserve some privacy.
- •Public relationships—especially with a globally famous actor going through his own public turmoil—taught her how invasive and distorting press coverage can be.
- •Even brief or early‑stage dating can be blown into “exclusive” stories that don’t match reality.
- •In a later, non‑famous relationship during the pandemic, paparazzi photos forced her to acknowledge it publicly just to set the record straight.
- •Says she constantly toggles between “fuck it, I’ll live my life” and wanting to protect love from external poison.
- •Admits she’s truly been in love once, with someone she can genuinely see a life with, but keeps details vague by choice.
- 1:52:40
The Next Chapter: Instinct‑Led Career, One‑Woman Show, And Motherhood
Closing the conversation, Jessie articulates a clear vision for her future: music and performance that are emotionally aligned, a passionate and diverse team around her, and equal investment in her personal life. She’s developing a one‑woman show that fuses therapy‑like honesty, comedy, and her full vocal ability, and she is consciously preparing her body and life to try for motherhood again with support.
- •Wants to act decisively on instincts rather than just trusting them privately.
- •Aims to make music that speaks as deeply to her as it does to others, not generic tracks others could sing.
- •Is actively looking for a team (especially management) whose passion, cultural awareness, and musical obsession match hers.
- •Developing a one‑woman show blending storytelling, emotional processing, laughter, and “singing as hard as I can.”
- •Preparing physically and emotionally to try again to become a parent, ideally not alone this time.
- •Says she’s clearer now that all her dreams—personal and professional—can and should happen with people by her side, not through extreme self‑reliance.
