TThe Diary of a CEO
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21 March 2022

Jaackmaate: The Untold Story Of My Battle With Health Anxiety & OCD

3Frameworks
14Insights

Frameworks in this episode

Insights & moments

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

Explainer· 3

Explainer13:00

How Self-Deprecating Humour Became Social Armour

Dean says he wanted acceptance at school and learned that clowning around brought attention. He later found that joking about himself first could disarm insults about his appearance, giving him a sense of control even as his school performance deteriorated.

  • He links disruptive behaviour to wanting laughs from popular classmates
  • He regrets how he treated teachers and apologizes to one by name
  • Calling himself the insult first made him feel harder to attack
  • He attributes his later academic decline more to fitting in than to a single cause

I'd want to be accepted a lot.

Jack Dean · 13:00

if you call yourself a ginger [ __ ] before them, disarming

Jack Dean · 16:00
#humour#school#belonging#self-deprecation
Explainer53:00

How a Creator Can Teach the Audience How to Treat Them

Bartlett suggests that Dean's blunt comic style has cultivated an audience that addresses him in the same language. Dean recalls young fans greeting him with insults at meet-and-greets as a sign of affection, illustrating how an online persona can shape the norms that later come back at the creator.

  • Dean's audience often mirrors his colloquial and insulting comic language
  • Fans may intend the language affectionately even when it feels jarring in person
  • Bartlett presents audience culture as one explanation for why Dean receives replies he would not expect himself
  • The discussion is an interpretation of Dean's audience, not a universal rule

you've cultivated a younger male audience that are comedic

Steven Bartlett · 53:30

because that's what I'm doing online.

Jack Dean · 54:30
#audience#persona#social-media#influence
Explainer1:07:00

Dean's Account of Living With Health Anxiety and OCD

Dean says a benign cyst found when he was 13 became an enduring trigger for intrusive fears about cancer. He describes recurrent conviction that he is ill, avoidance of checking part of his body or seeking a medical examination, and earlier rituals involving numbers, prayer, and a photograph; these are his reported experiences, not a clinical assessment made in the episode.

  • A doctor reportedly told Dean the lump was a cyst, but the fear persisted
  • He estimates that cancer fears convince him 15 to 20 times on some days
  • He describes childhood rituals that he believed were connected to his grandfather recovering
  • Cancer-related adverts and discussion can trigger alarm and thoughts about death
  • The interview does not diagnose the cause or establish that the condition can never change

there's probably 15 to 20 times a day where I actually convince myself that I have cancer

Jack Dean · 1:08:30

the cancer thing is something that really consumes my life

Jack Dean · 1:10:30
#health-anxiety#ocd#intrusive-thoughts#avoidance

Story· 8

Story05:00

Why Dean Keeps a Boundary With His Mother

Dean describes a childhood marked by his mother's alcohol problems, unstable contact, and events at home that he found harmful. He says distance has made his life richer and his mental state healthier, while leaving open the possibility of a future conversation rather than presenting reconciliation as an obligation.

  • Dean says he and his mother have had little contact for roughly eight or nine years
  • Late-night weekend messages make him question whether contact is driven by alcohol
  • He believes family members need boundaries just as friends do
  • He says reconnection may be possible one day but not now

I need to have boundaries with everybody in my life, not just like my friends

Steven Bartlett · 06:00

my life has been richer and mentally I've been a lot healthier without her in my life

Jack Dean · 12:30
#family#boundaries#childhood#estrangement
Story07:00

The Fatal Fight Behind His Father's Rule to Walk Away

Dean says his father went to prison for manslaughter after a man died following a fight outside a pub. He does not excuse what happened, but says his father still lives with it and taught him never to prove himself through a fight when he can walk away.

  • Dean describes the death and conviction as a lasting burden for his father
  • He explicitly says the act was not right
  • His father's lesson was to run from fights rather than act like the big man
  • Dean also describes his father as an early supporter of his YouTube work

if you ever get in any fights like you run away

Jack Dean · 07:30

he trusted that I saw something in it even if he didn't

Jack Dean · 09:00
#fatherhood#violence#consequences#support
Story30:00

Why Buying His House Left Dean Asking What Comes Next

Dean says he spent years saving with the single goal of buying a house outright, then largely stopped uploading after he achieved it. He felt proud and fortunate, yet describes walking around the house without feeling happier than when he rented; both speakers interpret the journey and forward motion as more rewarding than arrival.

  • Buying a house had dominated Dean's financial focus
  • He says the achievement coincided with losing his reason to keep uploading
  • The pride of ownership did not create the lasting emotional change he expected
  • The speakers frame purpose and continued movement as important, but do not establish a clinical mechanism

what do I do now then?

Jack Dean · 31:00

the journey is way more fun than the arrival

Jack Dean · 31:30
#goals#achievement#purpose#motivation
Story50:30

Why Deleting Twitter Did Not End Dean's Reply Loop

Dean says hostile replies can hit his ego even when he publicly frames responding as fun. He has deleted Twitter from his phone several times, but recalls reinstalling it before one dinner ended; he admits that critics often do get into his head and that replying gives him a short-lived rush.

  • Dean distinguishes his stated reason for replying from the ego reaction underneath
  • Fiona repeatedly encourages him to leave hostile replies alone
  • He describes deleting, reinstalling, replying, and later deleting replies as a recurring loop
  • He agrees that disengaging would probably make life happier but cites boredom as a pull back

I think sometimes it's because it's like hit me in the ego.

Jack Dean · 51:00

Nine times out of 10 you are in my head.

Jack Dean · 56:30
#twitter#trolls#ego#habits
Story58:00

The Five-Episode Pivot That Made Happy Hour Feel Right

Dean says Happy Hour began as an extension of his YouTube-drama commentary, built around calling people out. After roughly five or six episodes, he found the format poisonous and misaligned, shifted toward guest interviews, and rediscovered his enjoyment of making YouTube content.

  • Dean had wanted to interview people since studying interview techniques at college
  • The first version of Happy Hour copied the commentary model he was already tiring of
  • He and the team dropped the drama format after about five or six episodes
  • A major early guest helped establish credibility with later invitees

this is just poisonous and I don't it's not me

Jack Dean · 1:00:00

started getting guests on and interviewing people and I found the love of YouTube again

Jack Dean · 1:00:00
#podcasting#pivot#interviews#creative-work
Story1:14:30

The Drinking Pattern Dean Links to Escaping Intrusive Thoughts

Dean says alcohol can temporarily quiet his intrusive thoughts, which has led him to continue drinking alone after friends stop because he does not want sober fears to return. He connects the pattern with severe sleep disruption and monitoring sunrise times, while stressing that it happens less often than it once did; this is a personal account, not evidence that alcohol treats anxiety or OCD.

  • Dean describes drinking as temporary escape rather than recovery
  • He says sobering up can prompt him to continue drinking to delay the return of intrusive thoughts
  • Night-time fear and pressure to sleep before work reinforce his attention to sunrise
  • He estimates that very late drinking nights now occur around twice a month
  • Nothing in the episode supports alcohol as a safe treatment

I don't want my thoughts back again.

Jack Dean · 1:15:30

It's such a release for me, such a break from my everyday thoughts.

Jack Dean · 1:20:00
#alcohol#self-medication#insomnia#intrusive-thoughts
Story1:20:30

How Fiona Helped Dean Through a Workday He Felt Unable to Face

Dean recalls telling Fiona that anxiety and OCD made him feel unable to present for West Ham. She said she would not force him, then packed his equipment, ran a bath, booked a hotel, and prepared the route forward; he completed the job and later told her he needed that kind of push.

  • Dean describes Fiona as a patient listener during difficult nights
  • She reduced practical friction before he felt ready to leave
  • She combined reassurance with concrete preparation rather than an argument
  • Dean says completing the work prevented a longer period of self-reproach
  • This is one couple's experience, not a clinical intervention

I'm not going to force you.

Fiona South, quoted by Jack Dean · 1:21:30

I need you to just push me into things.

Jack Dean · 1:22:00
#relationships#support#anxiety#work
Story1:28:00

From Pre-Show Panic to Feeling at Home on Stage

Dean says he was shaking and close to a panic attack before opening for Max Fosh, with notes written on his hand already sweating away. Once introduced, he felt able to apply lessons learned from comedians, slow down, use pauses, and engage the audience; the success convinced him to pursue more stand-up.

  • Dean distinguishes intense anticipatory fear from how he felt once performing
  • Earlier stand-up attempts had been rushed because he wanted them to end
  • During this performance he says he stayed present and left space for timing
  • The positive experience changed his belief about whether he could do stand-up

I pretty much had a panic attack before I went out.

Jack Dean · 1:28:30

I was in the moment and I was able to live in the moment

Jack Dean · 1:29:30
#stand-up#panic#performance#confidence

Q&A· 1

Q&A1:12:30

Why Fear of a Diagnosis Keeps Dean From Seeking Help

Asked about overcoming health anxiety and OCD, Dean says he is not the right person to advise others because fear of confirmation prevents him from entering a doctor's office or beginning therapy. He encourages other people with health worries to seek medical or psychological help, mentions occasionally using an OCD workbook, and openly says he cannot currently follow his own advice.

  • Dean fears that confirmation of illness would cause him to shut down
  • He recognizes that this response is part of the problem rather than sound medical reasoning
  • He encourages others to have concerning symptoms checked and to talk to someone about mental distress
  • An OCD workbook is the only self-help resource he says he uses periodically
  • The episode offers no treatment plan or evidence that avoidance is safe

I would actively encourage people to go and talk to someone

Jack Dean · 1:13:00

I can't practice what I preach.

Jack Dean · 1:13:30
#healthcare-avoidance#therapy#ocd#health-anxiety

Takeaway· 2

Takeaway18:00

Recognising the Anger He Associates With His Father

Dean says he actively rejected traits he disliked in his mother but still notices a quick internal anger that he associates with his father. He reports that identifying the possible source and accepting a prompt from Fiona helps him regain perspective when trivial setbacks, such as editing software crashing, trigger it.

  • Dean frames the family link as his own interpretation
  • He says the anger appears around minor frustrations rather than fights with other people
  • Pinpointing the pattern helps him interrupt it
  • Fiona sometimes gives him an external cue to calm down

I actively had to not take them on myself.

Jack Dean · 18:30

if I can pinpoint it on something, I'm a lot better

Jack Dean · 19:30
#anger#family-patterns#self-awareness#relationships
Takeaway34:00

The Uses of Money That Felt Better Than Buying a House

Dean revises the claim that money buys happiness into a narrower view that money can buy freedom. He says helping his grandfather, paying for his sister's glucose-monitoring device, and covering his late dog's ashes felt more meaningful than buying his home, while also describing guilt about earning more than people doing socially vital work.

  • Dean distinguishes freedom from an unlimited rise in happiness
  • He describes transferring money to his grandfather after seeing his worn work clothes
  • He pays for a device his sister uses to monitor type 1 diabetes
  • Helping family gives him a sense that his online career has practical value

money buys freedom.

Jack Dean · 34:30

I got more out of that than I did when I bought my house.

Jack Dean · 35:30
#money#freedom#family#meaning