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Craig Oliver

@craigoliver100.bsky.social
199 followers 116 following 363 posts

Global head of Strategy and Reputation at FGS. Podcast: Desperately Seeking Wisdom. Was David Cameron’s Director of Politics and Communications - and before that Editor, BBC News at 6 and 10.

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Craig Oliver @craigoliver100.bsky.social · 11h
I quote Maya Angelou in my latest Desperately Seeking Wisdom Substack. It’s about how brave and thoughtful leaders are learning to show their working more. Check it out by clicking below…
craigoliver.substack.com
Show Your Working
For years, sounding uncertain was a sign of weakness. But the tide is turning, and the people worth listening to are the ones brave enough to admit downsides to their decisions. That’s a good thing.
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Craig Oliver @craigoliver100.bsky.social · 20h
A short video on why I’m writing about how the tide is turning in how we communicate. You can check out the full piece by clicking below. substack.com/@desperately...
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Craig Oliver @craigoliver100.bsky.social · 03/10/2026
The moment Theresa May tried to take revenge on me 👇. I write about it in my latest Desperately Seeking Wisdom Substack on the price we pay at work - check it out by clicking below…
craigoliver.substack.com
When we sell ourselves cheap
We often sell ourselves short - causing serious damage in the process - and only really notice when accounts are settled. How should we learn from the experience?
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Craig Oliver @craigoliver100.bsky.social · 01/10/2026
I write about not realising the cost of things until the bill arrives in my latest Desperately Seeking Wisdom Substack. You can check it out by clicking below…
craigoliver.substack.com
When we sell ourselves cheap
We often sell ourselves short - causing serious damage in the process - and only really notice when accounts are settled. How should we learn from the experience?
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Craig Oliver @craigoliver100.bsky.social · 30/09/2026
Why we do things that cost us dear 👇. I write about it in my latest Desperately Seeking Wisdom Substack. You can check it out by clicking below…
craigoliver.substack.com
When we sell ourselves cheap
We often sell ourselves short - causing serious damage in the process - and only really notice when accounts are settled. How should we learn from the experience?
001
Craig Oliver @craigoliver100.bsky.social · 29/09/2026
The key question at the centre of my latest piece on when we sell ourselves cheap. Check it out by clicking below…
craigoliver.substack.com
When we sell ourselves cheap
We often sell ourselves short - causing serious damage in the process - and only really notice when accounts are settled. How should we learn from the experience?
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Craig Oliver @craigoliver100.bsky.social · 28/09/2026
Stripping out cost and value 👇. Part of my Desperately Seeking Wisdom piece about selling ourselves short. You can check it out, by clicking below…
craigoliver.substack.com
When we sell ourselves cheap
We often sell ourselves short - causing serious damage in the process - and only really notice when accounts are settled. How should we learn from the experience?
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Craig Oliver @craigoliver100.bsky.social · 27/09/2026
A short video on why I’m writing about how we sometimes sell ourselves cheap - and the lessons from it. Check out the full piece Deaperately Seeking Wisdom piece by clicking below: open.substack.com/pub/craigoli...
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Craig Oliver @craigoliver100.bsky.social · 24/09/2026
I reflect on watching the nuclear war drama Threads in my latest Desperately Seeking Wisdom piece. It’s about how we should react to claims AI will destroy us. Check it out by clicking below 👇.
open.substack.com
If AI could destroy us, why aren’t we screaming?
Smart people tell us there’s a significant chance AI will destroy humanity. How should a wise person deal with those claims?
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Craig Oliver @craigoliver100.bsky.social · 23/09/2026
How should react to growing claims AI could kill us all? You can read my my latest Desperately Seeking Wisdom Substack by clicking below…
open.substack.com
If AI could destroy us, why aren’t we screaming?
Smart people tell us there’s a significant chance AI will destroy humanity. How should a wise person deal with those claims?
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Craig Oliver @craigoliver100.bsky.social · 22/09/2026
How should we react to claims there’s a good chance AI will destroy us all? You can read my whole Desperately Seeking Wisdom piece below…
open.substack.com
If AI could destroy us, why aren’t we screaming?
Smart people tell us there’s a significant chance AI will destroy humanity. How should a wise person deal with those claims?
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Craig Oliver @craigoliver100.bsky.social · 21/09/2026
How should a wise person cope with claims there’s a strong chance AI will kill us all? I writer about it in my latest Desperately Seeking Wisdom Substack. You can check it out, by clicking below…
open.substack.com
If AI could destroy us, why aren’t we screaming?
Smart people tell us there’s a significant chance AI will destroy humanity. How should a wise person deal with those claims?
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Craig Oliver @craigoliver100.bsky.social · 20/09/2026
A short video on why I’m writing about living with claims AI could kill us all. You can read my whole Deaperately Seeking Wisdom piece by clicking below. open.substack.com/pub/craigoli...
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Craig Oliver @craigoliver100.bsky.social · 16/09/2026
The historian Anthony Seldon tells us we have a choice as we age. I write about it in my latest Desperately Seeking Wisdom Substack. Check it out by clicking below… open.substack.com/pub/craigoli...
open.substack.com
Old and Better, Not Old and Bitter
The real question of ageing is whether you stay open - or quietly close the door on life. Here’s my plan to keep it open.
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Craig Oliver @craigoliver100.bsky.social · 14/09/2026
I write about ageing in a way that makes us better not bitter in my latest Desperately Seeking Wisdom Substack. You can check it out by clicking below…
open.substack.com
Old and Better, Not Old and Bitter
The real question of ageing is whether you stay open - or quietly close the door on life. Here’s my plan to keep it open.
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Craig Oliver @craigoliver100.bsky.social · 13/09/2026
The gravitational pull of life is towards closing down. I write about remaining open in my latest Desperately Seekimg Wisdom Substack. Check it out by clicking below…
open.substack.com
Old and Better, Not Old and Bitter
The real question of ageing is whether you stay open - or quietly close the door on life. Here’s my plan to keep it open.
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Craig Oliver @craigoliver100.bsky.social · 13/09/2026
My Desperately Seeking Wisdom Substack this week is about facing one of life’s big choices… open.substack.com/pub/craigoli...
open.substack.com
Old and Better, Not Old and Bitter
The real question of ageing is whether you stay open - or quietly close the door on life. Here’s my plan to keep it open.
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Craig Oliver @craigoliver100.bsky.social · 12/09/2026
Different parenting styles can cause real and lasting damage. I write about it in my latest Desperately Seeking Wisdom Substack - you can check it out by clicking below…
open.substack.com
A Little Rain
We swung, in a single generation, from neglecting our children to over-protecting them. Both produced major casualties? Wisdom helps us find a way...
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Craig Oliver @craigoliver100.bsky.social · 09/09/2026
Is the famous opening to Angela’s Ashes true? 👇 I write about the extremes of parenting styles - and their impacts in my latest Desperately Seeking Wisdom substack. You can check it out by clicking below.
open.substack.com
A Little Rain
We swung, in a single generation, from neglecting our children to over-protecting them. Both produced major casualties? Wisdom helps us find a way...
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Craig Oliver @craigoliver100.bsky.social · 08/09/2026
Boredom was a very big side effect of parenting my generation. I write about the pros and cons in my latest Desperately Seeking Wisdom Substack. You can check it out by clicking below…
open.substack.com
A Little Rain
We swung, in a single generation, from neglecting our children to over-protecting them. Both produced major casualties? Wisdom helps us find a way...
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Craig Oliver @craigoliver100.bsky.social · 07/09/2026
The opening to my latest Desperately Seeking Wisdom Substack on how different parenting styles have added to mental health issues 👇. Check it out by clicking below…
open.substack.com
A Little Rain
We swung, in a single generation, from neglecting our children to over-protecting them. Both produced major casualties? Wisdom helps us find a way...
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Craig Oliver @craigoliver100.bsky.social · 06/09/2026
A short video on why my latest Desperately Seeking Wisdom Substack is called A Little Rain. You can check out the full piece by clicking on the link below… open.substack.com/pub/craigoli...
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Craig Oliver @craigoliver100.bsky.social · 05/09/2026
A friend has “For God’s sake - be kind!” tattooed on his arm. It got me thinking - what’s the one thing I need to be constantly reminded of? What’s yours? I write about it in my latest Desperately Seeking Wisdom Substack. Check it out by clicking below…
open.substack.com
The Hardest Thing
The wisest people keep giving the same advice. It is simple, universal - and the hardest thing to actually do.
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Craig Oliver @craigoliver100.bsky.social · 01/09/2026
My latest Substack is about learning to let go - and how hard that can be when our reactions are instantaneous. You can check out the full piece by clicking below…
open.substack.com
The Hardest Thing
The wisest people keep giving the same advice. It is simple, universal - and the hardest thing to actually do.
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Craig Oliver @craigoliver100.bsky.social · 31/08/2026
I write about the things we struggle to let go - from minor irritations to deep-seated traumas - in my latest Desperately Seeking Wisdom Substack. Check it out by clicking below…
open.substack.com
The Hardest Thing
The wisest people keep giving the same advice. It is simple, universal - and the hardest thing to actually do.
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Craig Oliver @craigoliver100.bsky.social · 30/08/2026
A short video on my latest Desperately Seeking Wisdom Substack. You can read the full thing by clicking below… open.substack.com/pub/craigoli...
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Craig Oliver @craigoliver100.bsky.social · 29/08/2026
Simon and Garfunkel’s The Sound of Silence is prophecy of a divided social media world. I write about it in my latest Desperately Seeking Wisdom Substack. You can check it out by clicking below…
open.substack.com
When Silence Isn’t Golden
We’re taught that silence is precious. But life often shows us something different: it becomes whatever we place in front of it. We need to understand that to make the most of it.
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Craig Oliver @craigoliver100.bsky.social · 28/08/2026
I write about understanding the power of silence for good and ill in my latest Desperately Seeking Wisdom Substack. Check it out by clicking below…
open.substack.com
When Silence Isn’t Golden
We’re taught that silence is precious. But life often shows us something different: it becomes whatever we place in front of it. We need to understand that to make the most of it.
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Craig Oliver @craigoliver100.bsky.social · 27/08/2026
I quote Gandhi in my latest Desperately Seeking Wisdom Substack on when silence isn’t golden. Check out the full thing by clicking below…
open.substack.com
When Silence Isn’t Golden
We’re taught that silence is precious. But life often shows us something different: it becomes whatever we place in front of it. We need to understand that to make the most of it.
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Craig Oliver @craigoliver100.bsky.social · 26/08/2026
I quote words attributed to Martin Luther King in my latest Desperately Seeking Wisdom Substack. It’s a reminder that silence isn’t always golden. You can check it out by clicking below….
open.substack.com
When Silence Isn’t Golden
We’re taught that silence is precious. But life often shows us something different: it becomes whatever we place in front of it. We need to understand that to make the most of it.
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Craig Oliver @craigoliver100.bsky.social · 25/08/2026
More than sixty years on Simon and Garfunkel’s The Sound of Silence feels like a a prophecy about the age of social media. I write about it in my latest Deaperately Seeking Wisdom Substack - When Silence isn’t Golden. Check it out by clicking below…
open.substack.com
When Silence Isn’t Golden
We’re taught that silence is precious. But life often shows us something different: it becomes whatever we place in front of it. We need to understand that to make the most of it.
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Craig Oliver @craigoliver100.bsky.social · 23/08/2026
Silence isn’t always golden - despite so much emphasis on that claim. I write about it in my latest Desperately Seeking Wisdom Substack. Check it out be clicking below…
open.substack.com
When Silence Isn’t Golden
We’re taught that silence is precious. But life often shows us something different: it becomes whatever we place in front of it. We need to understand that to make the most of it.
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Craig Oliver @craigoliver100.bsky.social · 23/08/2026
A short video on why I’m writing about why it’s too easy to say silence is golden. You can check out the full piece by clicking below… open.substack.com/pub/craigoli...
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Craig Oliver @craigoliver100.bsky.social · 21/08/2026
I write about the insane task of being commissioned to write an 80,000 word book in less than three months in my latest Substack. It’s about coming to terms with the increased pressure to work and deliver… Check out the full piece by clicking below…
open.substack.com
Imagining All of Us Happy
August used to be a moment of tranquility amid a storm of activity. No longer. How do we resist the pull to drive on instead of finding time to reflect and rest?
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Craig Oliver @craigoliver100.bsky.social · 19/08/2026
In his essay, The Myth of Sisyphus comes to the seemingly perverse conclusion: One must imagine Sisyphus happy.” I write about why I’ve realised he’a right in my latest Substack. Check it out by clicking below… open.substack.com/pub/craigoli...
open.substack.com
Imagining All of Us Happy
August used to be a moment of tranquility amid a storm of activity. No longer. How do we resist the pull to drive on instead of finding time to reflect and rest?
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Craig Oliver @craigoliver100.bsky.social · 19/08/2026
In his essay the Myth of Sisyphus, Albert Camus asserts: “One must imagine Sisyphus happy.” It seems a perverse conclusion - but I explore why I’ve realised he’s right in my latest Substack. Check it out by clicking below…
open.substack.com
Imagining All of Us Happy
August used to be a moment of tranquility amid a storm of activity. No longer. How do we resist the pull to drive on instead of finding time to reflect and rest?
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Craig Oliver @craigoliver100.bsky.social · 17/08/2026
Too often our behaviours are dictated by the vanishingly few times we hit the jackpot. I write about how we can try to find a balance in my latest Substack. Check it out by clicking below…
open.substack.com
Imagining All of Us Happy
August used to be a moment of tranquility amid a storm of activity. No longer. How do we resist the pull to drive on instead of finding time to reflect and rest?
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Craig Oliver @craigoliver100.bsky.social · 17/08/2026
I write about Albert Camus’ The Myth of Sisyphus 👇in my latest Desperately Seeking Wisdom Substack. It seems a bleak way of looking at things - but in reality there is real hope and even happiness to be found in his philosophy. Find out why by clicking below… open.substack.com/pub/craigoli...
open.substack.com
Imagining All of Us Happy
August used to be a moment of tranquility amid a storm of activity. No longer. How do we resist the pull to drive on instead of finding time to reflect and rest?
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Craig Oliver @craigoliver100.bsky.social · 16/08/2026
I start my latest Substack by describing an anxiety dream that’s recurred for decades👇. It’s part of a piece about knowing when to push - and when to rest and reflect. You can check it out by clicking below… open.substack.com/pub/craigoli...
open.substack.com
Imagining All of Us Happy
August used to be a moment of tranquility amid a storm of activity. No longer. How do we resist the pull to drive on instead of finding time to reflect and rest?
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Craig Oliver @craigoliver100.bsky.social · 16/08/2026
A short video on why I’m writing about the August tension between having rest and reflection - and the constant drive to get things done. Check out the whole piece by clicking below: open.substack.com/pub/craigoli...
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Craig Oliver @craigoliver100.bsky.social · 15/08/2026
Coming to terms with how small we are compared with the cosmos👇. You can check out the whole piece by clicking below…
open.substack.com
Winning the Lottery a Trillion Times Over
There's nothing so mind-scrambling as being reminded of how inconsequential while focused on things we really care about. Here's what I learned when it happened to me...
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Craig Oliver @craigoliver100.bsky.social · 14/08/2026
Trying to get things into perspective - what do the mind-boggling scales of the universe and our bodies have to teach us? You can check out my full Substack by clicking below…
open.substack.com
Winning the Lottery a Trillion Times Over
There's nothing so mind-scrambling as being reminded of how inconsequential while focused on things we really care about. Here's what I learned when it happened to me...
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Craig Oliver @craigoliver100.bsky.social · 12/08/2026
I quote the novelist, John Barth 👇in my latest Desperately Seeking Wisdom Substack. He nails our need to create a narrative we are at the centre of, despite being almost irrelevant in global terms. How to navigate this? Check out the whole piece by clicking below… open.substack.com/pub/craigoli...
open.substack.com
Winning the Lottery a Trillion Times Over
There's nothing so mind-scrambling as being reminded of how inconsequential while focused on things we really care about. Here's what I learned when it happened to me...
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Craig Oliver @craigoliver100.bsky.social · 11/08/2026
Having a healthy sense of our place in the universe is one way of working out what really does ans doesn’t matter. I write about this in my latest Deaperately Seeking Wisdom Substack. Check it out by clicking below.
open.substack.com
Winning the Lottery a Trillion Times Over
There's nothing so mind-scrambling as being reminded of how inconsequential while focused on things we really care about. Here's what I learned when it happened to me...
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Craig Oliver @craigoliver100.bsky.social · 10/08/2026
How dow we come to terms with how infinitesimally small and inconsequential makes us appear? I write about this in my latest Desperately Seeking Wisdom Substack. You can check it out be clicking below…
open.substack.com
Winning the Lottery a Trillion Times Over
There's nothing so mind-scrambling as being reminded of how inconsequential while focused on things we really care about. Here's what I learned when it happened to me...
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Craig Oliver @craigoliver100.bsky.social · 09/08/2026
Coming to terms with our astronomical insignificance - while caring deeply about the people and things in front of us 👇. You can check out my latest Desperately Seeking Wisdom Substack by clicking on below…
open.substack.com
Winning the Lottery a Trillion Times Over
There's nothing so mind-scrambling as being reminded of how inconsequential while focused on things we really care about. Here's what I learned when it happened to me...
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Craig Oliver @craigoliver100.bsky.social · 09/08/2026
A short video on why I’m writing about being confronted with the fact we are infinitesimally small - when our issues seem so big…And what to do about it. Check out my full Desperately Seeking Wisdom Substack by clicking below… open.substack.com/pub/craigoli...
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Craig Oliver @craigoliver100.bsky.social · 06/08/2026
Three short sentences which radically change how we navigate the world 👇. I write about this in my latest Desperately Seeking Wisdom Substack. Check it out by clicking below…
open.substack.com
Through a Glass Darkly
Understanding the limits of our view and perspective is the route to a more enlightened and forgiving life.
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Craig Oliver @craigoliver100.bsky.social · 04/08/2026
The lens we use to look at the world defines how we interpret it - as Steinbeck points out in the first pages of Cannery Row 👇. I write about understanding the limits of our perspective in my latest Desperately Seeking Wisdom Substack. You can read it by clicking below…
open.substack.com
Through a Glass Darkly
Understanding the limits of our view and perspective is the route to a more enlightened and forgiving life.
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Craig Oliver @craigoliver100.bsky.social · 03/08/2026
I use George Eliot’s mirror and candle metaphor from Middlemarch to explain how we force false and egocentric thinking on the world in my latest Substack. You can check it out by clicking below…
open.substack.com
Through a Glass Darkly
Understanding the limits of our view and perspective is the route to a more enlightened and forgiving life.
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