Crocs, Socks, and a Crusty Old Stick.
Last night, just before dark…
When I was out on the farm doing my final rounds for the evening…
I noticed something was eerily off with the cows.
Every one of them was frozen.
Eyes locked.
Not on me – but on the woods.
Just seconds before, I’d been checking the hives…
The bees quietly humming their evening lullaby, when suddenly, the unmistakable sound of branches breaking echoed out of the darkness.
My heart started to thud in my chest, and there it was – a massive shadow, lumbering closer and closer to me through the trees.
A bear.
And not a small one.
* * *
There are certain moments when reality becomes surreal.
There I stood, alone in the darkness…
Face to face with an adult black bear.
Armed with nothing but a crusty old stick, and (of course) my deeply regrettable fashion choice – Crocs with socks.
It was a moment that made me feel wildly unprepared, vulnerable, and exposed.
But it also brought me instantly back to another moment – one you might remember from [Issue #023] “The Secret Power of Being Unprepared.”
A moment when I found myself wide awake at 1:27 AM in a UK hotel room, my heart pounding for a completely different reason…
Staring at the ceiling, realizing I was hours away from stepping onto a stage with an unfinished keynote for Chris Ducker’s event, in front of over a hundred paying attendees…
Both stories share a single, uncomfortable truth:
There is something deeply raw and real about being unprepared.
And when you share those kinds of stories – the messy, authentic, unfiltered ones – people can’t help but lean in.
The proof?
According to my Google Analytics account:
[Issue #023] where I tell the play-by-play story of being massively unprepared before my UK Keynote…
Is one of my all-time highest “time spent on page” issues of The Digital Contrarian…
Because a compelling story doesn’t just capture attention – it creates a connection between you and your reader.
In fact, I believe storytelling isn’t merely a “nice-to-have” skill in this post-AI era.
In our fractured, distracted, and increasingly disconnected digital world, I believe….
It might just be the single most scalable skill you can develop.
Because stories travel and stories stick.
Stories are how you sell product.
Stories are how you raise money.
Stories are how you recruit employees and partners.
And as Yuval Noah Harari argues in Sapiens, stories are what enabled humans – mere hairless apes – to transcend small tribes and scale up to global civilizations.
We cooperate, coordinate, and collaborate at massive scales – not because of logic or force, but because of the common fictions, narratives, and stories we share.
So today, I want to dive into the skill and science of storytelling.
Because as someone who’s spent the last week curating the stories I’m going to tell in my upcoming book – Return to Real…
I’ve realized something profound:
If the best things in life don’t scale, one thing absolutely does.
Stories.
And that makes storytelling arguably the most valuable skill we can refine as entrepreneurs…
Because in this world of fractured realities, short attention spans, and AI-generated content…
He or she who can cut through the clutter and tell the best story…
Wins.
So let’s talk about how.
1 | What 145+ Stories Taught Me About Scale, Connection, and Winnie the Pooh.
Over the last week, with the help of ChatGPT – I’ve been neck-deep in curating stories for my upcoming book:
Right now, I’ve got 145+ stories (and counting…) that have passed through my fingertips – each one a snapshot of a life, a business, or a moment when someone chose to take the road less traveled.
It’s been an illuminating process.
Because as you may know, one of the contrarian principles in the Return to Real is:
“The best things in life don’t scale.”
The stuff that truly fills us up (and what much of the world is craving) – the meaningful relationships, the slow food dinners, the deeply rewarding work – doesn’t come from optimizing, automating, and scaling to the nth degree.
It comes from depth, presence, and intentionality. The very things that digital tools (as seductive and convenient as they are) often strip away.
But as I’ve dug deeper into these 145+ stories, I’ve realized something fascinating:
Stories may be the exception to that rule.
Because while the best things in life don’t scale…
Stories – at their core – actually do.
Take a story we all know: Winnie the Pooh.
Photo Cred: E.H. Shepard
The story of Christopher Robin, Hundred Acre Wood, and a hunny-loving bear.
Is a familiar narrative shared by millions of us around the globe…
(With over 50 million copies sold, it’s one of the bestselling books of all-time…)
This text below (written by an anonymous Reddit user), and which I originally discovered from this Brent Lindeque piece is heartfelt, poignant, and demonstrates why this story is so powerful…
* * *
At the end of the Winnie-the-Pooh story…
Christopher Robin takes Pooh to the Enchanted Place at Galleons Lap and basically lets Pooh know in ambiguous terms that this is the end of their adventures together.
“You see,” began Christopher with a long sigh. “It’s like sleeping for a long, long time.”
Christopher Robin was surrounded by his friends under his favourite tree. It rested on the top of a hill overlooking the entire Hundred Acre Wood. He was older now, and he knew that he didn’t have much more time left with them.
“But going to sleep means that some day you’ll wake up.” Pooh said with a smile.
“Precisely!” Owl exclaimed.
“And we’ll be here when you do,” Kanga added. “I’ll even make you breakfast.”
Christopher couldn’t help but smile.
“I would very much like that. But you all have to understand that it will be a very, very long time.”
“Oh ho ho! We are great at waiting a long time! Rabbit here waits every year for the carrots to grow in the garden.” Tigger chimed in.
“And every year you destroy them!” Rabbit snarled.
“But Christopher!” Roo interjected, jumping into Christopher’s lap. “What are we going to do when you’re gone?”
“Oh I won’t be gone Roo. I’ll be right here.”
Christopher placed his finger over Roo’s heart. Roo giggled and scrunched up into a ball.
“We’ll be just fine,” muttered Eeyore. “I’m used to being alone anyways.”
“None of you will be alone! You’re a family now, and while I’m gone you will all take care of each other.”
“B-b-b-ut you will b-b-be back r-r-right Christopher?” Stuttered Piglett.
Christopher let out a soft sigh and looked around at all of his friends. It was going to be difficult to help them to understand. They probably never would…
Photo Cred: E.H. Shepard
“Sometimes good things come to an end. But here’s the secret everyone— come close!”
They all huddled together underneath the tree to listen to Christopher’s secret.
“Memories. Are. Forever.” He whispered and tapped Pooh on the nose.
“Memories?” Said Pooh. “Well I have plenty of those! Like that time we saved you from the Heffalumps!”
“Or when you helped me fix my garden!” cried Rabbit.
“Or when you organized my library for me!” Exclaimed Owl.
“Or that time you built me a new house out of those sticks you found in the woods.” Eeyore added sullenly. “It didn’t last the night…but I remember it.”
“Yes, yes! All of those are memories and you will have them forever. Just like I will have my memories of all of you.”
Christopher stood up and took one last look over the Hundred Acre Wood. The sun was setting in the orange autumn sky and the trees were beginning to lose their leaves.
It was time he went home.
Christopher gathered all of his friends together and began walking back down the hill. They were all busy discussing the memories they had had with each other.
“Christopher?” Pooh said, looking up at Christopher as they walked hand in hand. “You aren’t coming back, are you?”
Christopher looked down at the ground and took a moment before he responded.
“No Pooh. I won’t be coming back this time.”
They walked in silence, listening to the sound of the crunching leaves underneath their feet.
Pooh suddenly stopped and looked intently into the ground.
“I believe I am going to miss you Christopher,” he said with a soft, broken voice.
Christopher leaned down and took his lifelong friend into his arms.
“I will miss you too Pooh. I will miss you very, very much.”
* * *
This is not just a cute children’s tale.
Stories like Winnie the Pooh become so powerful precisely because they scale – across countries, cultures, and generations.
They’re viral before the word “viral” even existed, and yet their virality isn’t digital – it’s human.
In the case of Winnie the Pooh…
It’s a story about growing up…
About the end of childhood.
About death.
About grief.
About saying goodbye to the ones we love.
And it’s the shared stories like these that form the connective tissue that binds us together as a species.
* * *
In [Issue #054], “The Breakdown of Shared Reality,” I explored how we’ve lost so much of this connective tissue in our society.
With the fragmentation of traditional media, the splintering of shared narratives, and the algorithmic echo chambers we’ve found ourselves trapped in – our shared reality has frayed and fractured.
But contrast that with what Yuval Noah Harari argues in his book Sapiens:
“What allows humans to cooperate at scale isn’t reason or instinct – it’s fiction. It’s our capacity to tell shared stories.”
Harari makes a compelling case:
We’re not the fastest or strongest species.
We didn’t rise to dominance by raw power or logic alone.
Instead, we humans built civilizations, empires, and global communities because we learned to create shared imagined realities – stories.
Money, nations, religions – these aren’t objectively real entities. They’re stories we’ve collectively agreed upon. And they work because they scale.
In other words:
Storytelling isn’t just a soft skill.
It may just be the single most powerful and scalable technology humanity has ever developed.
So here I am, deep in these 145+ stories for the Return to Real – and it strikes me that in this post-AI world that we find ourselves in…
Storytelling might just be the most valuable skill worth focusing on.
Because after all, in a fragmented world that’s grown increasingly disconnected from the real and the true, he or she who can both seek and speak truth – and tell the best story – may just win.
And that’s why storytelling is something I’m personally working to get better at, to refine, and ultimately, to master…
Because the story I shared about my own bear-in-the-woods experience – Crocs, socks, stick and all – is reminiscent of something we explored together way back in [Issue #020] Going Analog. The Ultimate Post-AI Zig?
And that’s this…
For people to TRUST you they need to see three things:
Your Heart, Your Humor, and Your Humanity.
The world is hungry for all three right now.
The world is hungry for connection.
The world is hungry for what’s real.
And because of that…
In this post-AI, technical race-to-the-bottom era we find ourselves in…
Storytelling isn’t just the path to connection.
It might just be the most scalable skill we have left.
But the question is this…
2 | What Makes a Story Captivating (And Not Just "Nice")?
On paper, [Issue #023] “The Secret Power of Being Unprepared”was a mess.
There was NO framework. NO hook. And NO clear CTA.
Just the story of me – sitting wide awake at 1:27 AM in a Cambridge, UK hotel room, my heart racing, staring into the dark, completely unprepared for the keynote I was due to deliver in less than eight hours.
And yet it’s still one of the highest “time spent on page” issues I’ve ever published in The Digital Contrarian.
Why?
Because it was a compelling story.
And as humans, we’re wired for stories in ways we rarely stop to consider.
Consider the opening scene….
* * *
Sunday, November 17th (Cambridge, UK)
It’s 1:27 AM and I wake up with my heart pounding out of my chest.
I’m set to speak on stage in less than 8 hours.
My slides are not finished. My presentation is not done.
I have a rough idea of what I want to cover…
But I’ve never done this talk before…
This is brand new material.
And on top of that…
It’s my first time delivering a keynote in the UK…
And I’m starting to panic.
There are over 100+ people from all over the world who have paid to be at this event.
And Chris Ducker (my friend and organizer of the event, pictured with me above) is counting on me to deliver.
My heart starts racing as I lay there in bed, wide awake staring into the abyss.
I could hear a lifetime of voices in my head – my mom, my wife, my business partner, my dog:
“Why do you always do this? Why do you always wait until the last minute for everything?”
There’s no more time.
I need to wake up.
I need to figure out what I’m going to say…
* * *
Contrast this with your typical “optimized” content – well-structured, polished, and perfectly formatted.
Sure, it might be useful.
But memorable? Compelling? Not usually.
It feels clinical. It leaves no mark.
The reality is this: when storytelling is absent, your content – no matter how tactical or strategic – feels sterile and generic.
Readers skim, click away, and forget. There’s no emotional hook, no shared resonance, no lasting impact. No mirror neurons firing, no oxytocin released.
No connection is formed.
And connection is everything.
It’s the very thing Yuval Noah Harari argues in Sapiensallowed our species to build civilizations, empires, and global communities. Our ability to create and share imagined realities – stories – is the true currency of human cooperation.
* * *
Will Storr, in his book The Science of Storytelling, describes the human brain as essentially a storytelling machine. Our brains don’t simply record experiences – they encode them in narrative.
As Storr explains, “Stories help us simulate experience, build meaning from chaos, and understand ourselves and our world.”
He points out that great stories activate a chain reaction in the brain, pulling us into the minds of others, creating empathy, and helping us make sense of complex realities.
At its core, a story is a cause-and-effect simulation we genuinely care about. Our minds don’t just passively listen – they actively participate.
That’s why stories become sticky:
They imprint on us emotionally, neurologically, and deeply.
Compare that kind of narrative experience to memes.
Sure, memes are fun. They compress ideas and rapidly propagate, grabbing attention. But memes don’t deepen understanding.
They don’t create the sort of resonant trust that lasts. They’re surface-level dopamine hits. They’re brief, amusing, and they’re fleeting.
Stories, especially “mini-stories” (like the “Crocs and Socks” story above), pack a far more powerful punch.
They ground abstract ideas in concrete experiences, emotions, and transformations.
They bridge the gap between what is true and what is human.
Just think of the Winnie the Pooh excerpt you read a moment ago.
It’s not just a cute story. It’s a reflection on growing up, loss, grief, and the hard, universal truth of saying goodbye.
It connects because it speaks to something universal. It scales because it taps into shared human truths.
Stories – real stories – don’t just capture attention. They build connection.
And here’s why that matters now, more than ever:
In this era of fragmented realities, infinite feeds, and relentless AI-generated content.
As we discussed in [Issue #049] Why Oxytocin = The New Dopamine, the world has optimized for dopamine: clicks, likes, quick fixes, cheap thrills.
But what people are truly craving?
Meaning.
Connection.
Oxytocin.
And that’s the power of story.
So let’s explore how to tell a better story…
3 | The Three Story Types (And Why You Need All Three)
After compiling the 145+ stories for Return to Real, there is a pattern I’ve found helpful for thinking about what types of stories are worth sharing.
Every powerful, memorable story falls neatly into one of three distinct types.
And as entrepreneurs, leaders, and creators, understanding – and using – all three is essential to ensuring our stories resonate, stick, and inspire.
Here’s how to categorize them:
1st-Person Stories: “It Happened to Me”
These are your lived experiences – i.e. stories you personally walked through. They carry your unique voice, perspective, and vulnerability. They have authority because they’re deeply authentic. They’ve happened to YOU.
For example:
- Wide awake in bed 1:27 AM, unprepared for a keynote less than 8 hours…
- Facing a bear at dusk in my Crocs with socks, armed with nothing but a stick…
These stories resonate because they’re real. The audience feels your tension and triumph directly, in your voice, from your point of view.
When you tell a 1st-person story, you offer readers the gift of empathy – they step into your shoes and feel what you felt.
2nd-Person Stories: “It Happened to Someone I Know”
These stories center around people you’ve directly worked with or know personally – clients, colleagues, or peers.
They’re compelling because they add enough distance to highlight clear, instructive transformations without sacrificing authenticity.
For example:
- Ali Jafarian, founder of MemberDev who transitioned from burned-out technologist to outdoor adventure guide, and who is now loving life.
- Melissa Kwan, founder of eWebinar who chose to write openly about the struggles of bootstrapping a startup alone, and as a result started gaining traction in her business.
These stories land because they come from direct observation, interaction, and guidance. You’re sharing a story you’ve influenced, shaped, or witnessed first-hand.
When you tell a 2nd-person story, you illustrate a transformation. You make an abstract concept immediately relatable, believable, and achievable.
3rd-Person Stories: “It Happened Out There”
These are stories you reference from afar – famous people, historical examples, compelling case studies, or powerful ideas. They add weight, credibility, and broader context to your message.
For example:
- Nate Hagens explaining The Great Simplification and how energy drives our civilization.
- Yuval Noah Harari describing how shared fictions enabled humans to scale cooperation in Sapiens.
These stories are powerful because they help you connect the dots on a larger scale. They anchor your ideas in context, making your content more relevant, timely, and credible.
When you tell a 3rd-person story, you add authority and perspective, broadening your reader’s aperture and validating your message.
Why You Need All Three
Here’s the thing:
You don’t choose just one. You need all three.
Your 1st-person stories establish intimacy and authenticity. Your 2nd-person stories provide practical evidence of transformation. Your 3rd-person stories add broader credibility and context.
Together, they form an comprehensive narrative:
- 1st-person stories build emotional connection and authenticity.
- 2nd-person stories demonstrate practical transformation and achievable results.
- 3rd-person stories position your ideas within broader societal, historical, or cultural contexts, reinforcing your core insights.
You want to strategically weave together all three types to make your content meaningful, memorable, and genuinely impactful.
Because when you blend these story types seamlessly, something powerful happens:
Your message stops sounding like theory.
It stops feeling abstract.
It starts feeling true.
And it starts feeling real.
By the way – if YOU have a unique and compelling Return to Real story, or you know a business or leader you admire whose story deserves to be shared in my upcoming book, please SHOOT ME AN EMAIL and tell me about it. I’m finalizing the list of stories as we speak and I’d love to hear from you.
4 | Five Practical (and Contrarian) Tips for Telling Better Stories.
By now, we’ve covered why storytelling matters and the three core types of stories you need in your toolkit.
But how do you actually tell better stories?
I’m not going to give you fluffy advice like “be authentic” or “be vulnerable” (although important) – but instead, practical contrarian tips you can put to use right away.
Here are five to get you started:
1. Start With the Moment of Maximum Tension
Most storytelling advice suggests starting at the beginning – set the scene, provide context, build slowly, etc.
But here’s the contrarian take:
Forget context. Skip the setup. Drop your reader straight into the moment of maximum tension.
Just like how I opened [Issue #023] at 1:27 AM, wide awake, heart racing. Don’t ease into your story. Instead, go for a cold open – when your heart was pounding, when the stakes felt highest, and then quickly fill in the gaps.
This immediately grips attention, raises questions, and pulls readers along to find out what happens next.
2. Don’t Polish Too Soon (Or Too Much)
The common advice you’ll here is to edit ruthlessly, polish until perfect.
But perfect stories are predictable – and predictable is boring.
Instead, keep the awkward details. Embrace your heart, humor, humanity. Reveal your embarrassing choices (like Crocs with socks). Let readers see the messy edges of your experience.
Because the imperfections – the genuine details that others might remove – are what make your story feel human.
And raw and real stories are always more compelling than sanitized ones.
3. Say the Part Most People Skip
Most people edit out the uncomfortable details – the moments of doubt, vulnerability, or raw honesty – thinking they’re distracting or too personal. Like this image caption:
Because here’s the counterintuitive truth:
The parts you’re tempted to skip are precisely the parts your audience craves most.
Don’t censor yourself. If a detail feels slightly uncomfortable, slightly too revealing – you’re likely onto something powerful. Lean into it. Share it.
It’s these raw, overlooked moments that give your story emotional depth and authenticity.
4. Choose Details That Seem Irrelevant (But Aren’t)
Typical storytelling advice focuses on efficiency:
Stick to relevant details, cut anything extraneous.
But the contrarian truth?
The details that initially seem irrelevant – Crocs with socks and crusty sticks – are exactly what make stories memorable.
Irrelevant details make scenes vivid and tangible. They ground your reader in sensory experiences. They anchor emotion in physical reality.
5. Know the Transformation (Even When It’s Subtle)
Most advice suggests dramatic transformations – big life-changing moments, Hollywood-level stakes.
But here’s what’s counterintuitive:
The most powerful transformations are often subtle. Quiet. Internal.
Maybe you didn’t slay the dragon or overcome impossible odds. Maybe you simply learned something small, but profoundly important. Perhaps you changed your mind or saw a familiar situation in a new way.
Even subtle transformations matter deeply – because readers see their own lives reflected more clearly in quiet truths than epic adventures.
The bottom line is this:
Good storytelling isn’t just about structure or clever turns of phrase.
It’s about truth. It’s about courage. It’s about sharing the things most people leave unsaid.
Because when you do…
Your stories become not just interesting – they become irresistible.
And readers will hang onto every single word.
Which brings me to…
5 | One Final Story (And an AI Invitation...)
It’s no secret that I’ve had “mixed feelings” about where it most makes sense to inject AI into your business.
(Especially if you want to avoid commoditizing a human-centered “category of one” brand…)
But recently my thinking has evolved on this topic…
Because a few months ago when I hosted an intimate, high-level mastermind in Cambridge (Massachusetts) just outside MIT campus.
At that event – one of the attendees, Sam Woods, delivered a private session that had me blown away.
It was a session showing how he is using *Agentic AI* to get parts of his business to run semi-autonomously – and in some places, 100% autonomously – while preserving the authenticity of his content.
To provide a bit of context:
Sam isn’t your typical AI hype guy. He’s thoughtful, Swedish, deeply pragmatic – and very much aware that we’re in the midst of another gold rush moment in tech.
Sam spends most of his time implementing AI solutions for large, enterprise-scale clients – and is at the cutting edge of what’s actually possible with the technology right now.
* * *
Which brings me to earlier this week.
Sam and I were catching up on what’s changed with Agentic AI technology in the last few months with some of the most recent advancements.
(Turns out quite a bit…)
… And I asked him if he might be willing to give me an *update* on the state of where the technology is today…
AND do a bit of show-and-tell for me and a few people over Zoom to show what’s possible with Agentic AI for those of us who are interested in implementing some of this for ourselves.
Now, the reason I’m telling YOU this…
Is because with Sam’s permission, I’ve decided to open up the opportunity to join this Zoom session with me, to learn from Sam as he walks through actual real-life Agentic AI workflows that he’s setup to run autonomously.
Now to be clear…
This is NOT about “prompt engineering” with ChatGPT or anything basic like that (there plenty of places online covering how to do that right now…)
Instead, this is more advanced.
This is about using *Agentic AI* to connect multiple tools in your tech stack and get parts of your current business to run semi-autonomously, and in some places, 100% autonomously – saving you tons of time in the process.
So if you’re interested in learning how to do this yourself….
Or if you’re just curious to see what this looks like in action…
I will be holding a Live Zoom Session with Sam this week, and as a Digital Contrarian subscriber, I’d like to invite you to sit in on this session with me.
Here’s the link to register:
“How to Use *Agentic AI* to Get Parts of Your Business to Run 100% Autonomously (& Free More Time to Live Your “Return to Real” Life…)
A Special Session With Sam Woods & Ryan Levesque
NOTE: Because this is going to be on my personal Zoom account, the meeting will max out at 300 people.
So if you’re interested, I highly recommend registering for this session now – and blocking off your calendar so you can grab one of the 300 available spots.
Make sense?
Okay cool.
* * *
Okay! Before we wrap things up, I’ll leave you with one final question to think about this week, and that’s this:
Based on everything we’ve explored together here in this issue…
Where might you tell a story instead of simply dropping more content this week?
Try it, see what happens, and report back to let me know…
You might just be surprised at the difference it makes…
And the impact it has on your business :-)
* * *
Okay, I’ll leave you with that for now…
Have a great rest of your day…
Remember to hug the ones you love…
And as always….
Until next week,
Ryan :-)
