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Diary of a CEO · 2023-03-16 · 2h 00m

Simon Sinek: "I FEEL LONELY!" How To Deal With Loneliness! | E230

Simon Sinek opens up about loneliness, mental fitness, and how successful relationships are acts of co-creation built on serving others.

Simon Sinek: "I FEEL LONELY!" How To Deal With Loneliness! | E230
The guest

Simon Sinek — Leadership and communication expert, TED speaker, and author of Start with Why and Leaders Eat Last; the most-returning guest on Diary of a CEO.

The gist

Simon Sinek returns to Diary of a CEO and candidly admits he is feeling lonely, reframing emotional struggle as 'mental fitness' rather than 'mental health.' He argues society teaches self-help but never how to help others, and shares his personal rule of 'no crying alone' plus the idea that friends should 'sit in the mud' rather than try to fix. The conversation moves through ADHD's effect on his relationships, dating apps turning love into shopping, and his '3+1' framework for great relationships. Host Steven Bartlett shares his own vulnerability with his girlfriend, framing relationships as co-creation. Simon closes with a long story from Afghanistan that crystallized his belief that the highest purpose is to serve those who serve others.

Big reveals

  • Simon reveals he is pivoting away from in-person public speaking to seek bigger impact and discomfort again.
  • He rejects the term 'mental health' in favor of 'mental fitness,' an ongoing practice with good and bad days like the gym.
  • Simon shares his personal rule with friends: 'no crying alone' and the metaphor of just needing someone to sit in the mud with him.
  • He admits he is a middle-aged man never married, calling himself 'pretty undatable' due to his career and ADHD.
  • Simon discloses he was diagnosed with ADHD at 32 and only now learning how its 'stonewalling' affects his relationships.
  • Simon and Steven independently arrive at the same '3+1' relationship framework: sexual, intellectual, and emotional compatibility plus circumstances.
  • Simon recounts a 24-hour Afghanistan trip, a rocket attack, and carrying a fallen soldier's casket home that birthed Leaders Eat Last.
  • A general's words 'Go on' (we're with you) versus the private sector's 'Take your time' became Simon's code for supporting struggling friends.

Things worth remembering

  • Theresa May was the first UK prime minister to appoint a minister for loneliness.
  • The median American once reported three people to turn to in crisis; that answer is now reportedly zero.
  • Simon argues meditation's real purpose is service to others: being fully present so a friend feels heard.
  • Simon claims there is nothing more dangerous in modern society than a lonely man, linking it to terrorism and mass homicide.
  • Shared struggle releases oxytocin, the bonding hormone, which is why families and societies grow closer through tragedy.
  • John Gottman can predict in five minutes whether a couple will survive by watching for eye-rolling, a sign of contempt.
  • Simon calls always saying 'I'm great' the most selfish thing you can do because it denies others the honor of being there for you.
  • Simon measures success by momentum, not achievement, always seeing only the 'tip of the iceberg' of his vision.
  • Simon notes he and Steven respect and like each other but have never actually gone out for a meal together.
  • Simon argues it takes more courage and strength to say 'I'm anxious today' than to lie and say everything is great.

Recommended in this episode

Books, products and media the guest or host genuinely endorsed here — with the buy link.

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Guest’s ownBook

Start with Why

Simon Sinek

“And I'm this back in the start with Y days. And I'm good at start with Y. Like I've done this thing probably thousands of times.” — Simon Sinek 00:08:21
Find it on Amazon
Guest’s ownBook

Start with Why

Simon Sinek

“I also discovered EMTT Rogers work on the law of diffusion of innovations which I did write about also in start with Y.” — Simon Sinek 00:35:33
Find it on Amazon
Guest’s ownBook

Leaders Eat Last

Simon Sinek

“because of that experience, that's where the book leaders eat last came from. That experience was the impetus for that book.” — Simon Sinek 01:48:39
Find it on Amazon
Guest’s ownBook

The Infinite Game

Simon Sinek

“We've used that analogy before, you and I, which is what the infinite game is, which is it's like I want to be healthy.” — Simon Sinek 00:22:33
Find it on Amazon