The Contrarian Digest [Week 15]
The Contrarian Digest is my weekly pick of LinkedIn posts I couldn’t ignore. Smart ideas, bold perspectives, or conversations worth having.
No algorithms, no hype… Just real ideas worth your time.
Let’s dive in [15th Edition] 👇
1️⃣ When High Performers Become the Problem – Nathalie Martinek, Ph.D.
⚡𝐈𝐧 𝐛𝐫𝐢𝐞𝐟: First praised for your “vision,” then pushed aside for using it. The silent punishment for those who dare question the unwritten rules.
🗞️𝐅𝐮𝐥𝐥 𝐩𝐨𝐬𝐭: https://lnkd.in/es6Uu2AD
2️⃣ 10 Everyday Rules for Surviving Modern Hostility – Shawnee Delaney
⚡𝐈𝐧 𝐛𝐫𝐢𝐞𝐟: What if the Cold War never ended, but just moved to your devices? Here are 10 CIA spy rules reimagined for your inbox, team, and digital life.
🗞️𝐅𝐮𝐥𝐥 𝐩𝐨𝐬𝐭: https://lnkd.in/en4W44Mi
3️⃣ The 7 Habits of Highly Mediocre People – Scott Caputo
⚡𝐈𝐧 𝐛𝐫𝐢𝐞𝐟: More often than not, “mediocrity” ISN’T a lack of talent. It’s about these everyday habits many have normalized as “playing it safe.”
🗞️𝐅𝐮𝐥𝐥 𝐩𝐨𝐬𝐭: https://lnkd.in/eUcGQPGC
4️⃣ The Self-Reflection Machine – Matt Lakajev
⚡𝐈𝐧 𝐛𝐫𝐢𝐞𝐟: The story (and playbook) of how using AI as a mirror might reveal patterns you’ve never seen about yorself. Can “AI as a mirror” rewire your thinking, identity, and output?
🗞️𝐅𝐮𝐥𝐥 𝐩𝐨𝐬𝐭: https://lnkd.in/ea5CV8B8
5️⃣ The Power of Opposite Experiments – David Heinemeier Hansson
⚡𝐈𝐧 𝐛𝐫𝐢𝐞𝐟: What if everything you’re certain about is WRONG? Testing the opposite of your convictions might be the most valuable experiment you never run.
🗞️𝐅𝐮𝐥𝐥 𝐩𝐨𝐬𝐭: https://lnkd.in/eBd6Efqg
6️⃣ When AI Buys for You (Checkout Extinction?) – Simon Taylor
⚡𝐈𝐧 𝐛𝐫𝐢𝐞𝐟: Google’s “agentic checkout” isn’t just a feature. It might be the death of an entire ecosystem. The battle for who owns the payment moment has begun.
🗞️𝐅𝐮𝐥𝐥 𝐩𝐨𝐬𝐭: https://lnkd.in/ejKFEGg3
7️⃣ Why REAL Creatives Still Matter – R.J. Abbott
⚡𝐈𝐧 𝐛𝐫𝐢𝐞𝐟: AI didn’t “democratize creativity.” It exposed how few ever dared to risk being misunderstood. Here’s why that matters more than ever.
🗞️𝐅𝐮𝐥𝐥 𝐩𝐨𝐬𝐭: https://lnkd.in/e7A_w5-V
💭𝐌𝐲 𝐭𝐚𝐤𝐞: The AI Fairy Tale: Beautiful story. Too bad it’s a lie – https://lnkd.in/eNjRErcG
8️⃣ Universes We Never Visit – Shashank Sharma
⚡𝐈𝐧 𝐛𝐫𝐢𝐞𝐟: Every choice collapses infinite possibilities into one fragile reality. What will you do with the universe you’ve chosen?
🗞️𝐅𝐮𝐥𝐥 𝐩𝐨𝐬𝐭: https://lnkd.in/eW_ebBna
9️⃣ BONUS: Inspiration is a moment, not a future – Gaetan Portaels
🗞️𝐅𝐮𝐥𝐥 𝐩𝐨𝐬𝐭: https://lnkd.in/eb26Xhef
——-
Which of these topics resonates with you the most?
Share your thoughts in the comments!
To your success,
Gaetan Portaels
Original publication date — May 26, 2025 (HERE)
READ THE FULL POSTS BELOW (and please, don’t forget to follow the authors)
1️⃣ When High Performers Become the Problem – Nathalie Martinek
From Favourite to Problem: the Scapegoat’s whiplash
Before the scapegoat is cast out, they are often held up—praised, trusted, even recruited with enthusiasm and promises of impact.
You may have been hired for your vision, admired for your insight, and relied upon for your ability to bring clarity where others hesitated. You were seen as the high performer, the bridge-builder, the problem-solver who made the team, the project, or the leader look good.
For a while, it worked. You brought results. You didn’t question too much. You aligned with the narrative and helped protect the image. You weren’t seen as a threat…yet.
Then something subtle shifted. The warmth cooled. The praise became less public and more conditional. The feedback turned vague, and suddenly, your presence in the room felt like too much.
You didn’t lose your skill, your clarity, or your impact. What changed was your containment. You started asking sharper questions, raising concerns that touched too close to someone’s comfort, naming dynamics that others preferred to leave unspoken.
What was once seen as confident became reframed as difficult. Your insight was now labelled as confrontational. Your commitment to truth was interpreted as disloyalty.
The same people who elevated you began to avoid you. The invitations slowed. The meetings went quiet. The story changed. quietly, and without your input.
This is the whiplash of the Scapegoat: when you realise you didn’t fall because you failed, but because you stepped on invisible lines you didn’t know were there—lines drawn to protect power, not integrity.
In systems built to preserve power and perception, you’re punished for crossing invisible lines no one warned you about. Lines that protect comfort, control, and unspoken rules.
You weren’t unstable. You stepped outside the script. And that was enough.
2️⃣ 10 Everyday Rules for Surviving Modern Hostility – Shawnee Delaney
“Cover your tracks. Be sneaky. Plan then do.”
That’s not from a spy thriller. A friend recently shared this gem from his kid’s notebook—his own personal spy rules. And I have to say… the kid gets it.
Simple. Sharp. Absolutely on brand.
It reminded me of the legendary Moscow Rules—a set of unwritten principles used by CIA operatives operating deep behind enemy lines during the Cold War.
And while most of us aren’t dodging the KGB…we are navigating hostile territory every day.
They weren’t just survival tactics. They were life-saving strategies for operating in hostile territory.
And here’s the kicker: we’re still in hostile territory.
In our inboxes
In our teams
On our devices
In our organizations
So here’s my take: We reimagine the Moscow Rules for the modern world.
Not just for spies—but for leaders, teams, parents, partners, and anyone online.
Let’s call them the New Moscow Rules and here are my top ten:
Assume nothing.
→ Assume compromise. Insider threats and accidental leaks are happening in plain sight. Don’t wait to be surprised—plan like you’re already in the blast zone.
Never go against your gut.
→ Your instincts are still your best firewall. If something feels off—a message, a meeting, a manager—it probably is. Gut-check before greenlighting.
Everyone is potentially under opposition control.
→ Anyone can be compromised. Stress, burnout, blackmail, gambling, AI deepfakes—humans are messy, and that’s the risk.
Don’t look back; you’re never completely alone.
→ Digital breadcrumbs are forever. Metadata, shared docs, keystroke logs. We’re never truly alone online—so operate accordingly.
Go with the flow; blend in.
→ Adaptation is your best security posture. In rigid systems, humans find workarounds. In flexible ones, they find safety.
Keep your options open.
→ Backup your backups. For your files, your people, your mental health. Contingency plans are kindness in disguise.
Keep your cover.
→ Protect your identity—digitally and emotionally. MFA, privacy settings, boundaries. Your cover story might be your real story.
Assume surveillance.
→ You’re always being watched—by algorithms, cameras, even your fridge. Operate with the dignity of someone who might get quoted.
Don’t attract attention.
→ Signal discipline is a modern superpower. Not everything needs to be shared, overshared, or posted.
Know your area.
→ Understand your landscape. In espionage, this is terrain. In life, it’s context. Who has access? Who has influence?
We don’t live in Moscow in the 1980s. We live in the age of phishing links, insider fraud, emotional manipulation, and AI-generated threats.
But the same rules still apply.
Because when you understand the human factor, you don’t just survive, you lead. You protect.
And maybe, just maybe, you raise a kid who writes “Be sneaky” like it’s gospel.
3️⃣ The 7 Habits of Highly Mediocre People – Scott Caputo
7 Habits Keeping You Mediocre:
(and how to change them today)
1. Avoiding Difficult Conversations
↳ Sidestepping necessary conflict prevents both relationship depth and problem resolution
↳ Mediocre performers sacrifice long-term progress for short-term comfort
2. Consuming More Than Creating
↳ Endless learning without application creates knowledge without results
↳ Mediocre performers prepare forever while high performers act with imperfect information
3. Following Conventional Wisdom
↳ Accepting standard approaches guarantees standard results
↳ Mediocre performers do what’s expected while exceptional ones question assumptions
4. Making Excuses Instead of Adjustments
↳ Explaining why something can’t be done consumes energy that could solve the problem
↳ Mediocre performers build sophisticated justification systems
5. Prioritizing Urgent Over Important
↳ Responding to immediate demands guarantees strategic work never happens
↳ Mediocre performers mistake motion for progress
6. Seeking Permission Before Action
↳ Waiting to be chosen or authorized creates permanent dependence
↳ Mediocre performers wait for perfect conditions while high performers create them
7. Avoiding Calculated Risks
↳ Playing it safe guarantees you’ll never discover your true potential
↳ Mediocre performers optimize for protection while high performers optimize for growth
Mediocrity isn’t caused by lack of talent.
It’s caused by these seemingly innocent habits that silently limit your potential day after day.
Which of these habits has been keeping you from excellence?
4️⃣ The Self-Reflection Machine – Matt Lakajev
I’ve had multi-week conversations with ChatGPT.
I mean 4–8 hours per day sometimes.
I uploaded:
→ Literal rants about my childhood
→ Every Skool post I’ve ever written
→ My workouts, my sleep data, even my food
→ Dozens of mental loops I’d never said out loud
→ 45-minute voice notes from my morning walks
And I asked it to help me see the patterns.
What I got back was insane.
Not just better output.
Not just clearer thinking.
What I got back was a version of myself that made more sense.
It made me realise there are 4 meta-skills you have to build if you want to actually use AI as a second brain.
Not prompts.
Not hacks.
Internal upgrades.
1. Identity Debugging
Willpower never worked for me.
But using GPT to reflect back why I do what I do?
That changed everything.
I realised I wasn’t struggling with discipline — I was stuck in patterns from childhood I hadn’t even questioned.
After one deep session, I stopped overeating at night.
Not because I forced myself.
Because I just didn’t see myself that way anymore.
I didn’t stop the habit. I outgrew the identity.
2. Cognition Scaffolding
You don’t need to “think harder.”
You need to offload the loop.
I used to carry unfinished IP in my head for weeks.
Now I record my thoughts, upload them, talk them through, structure the logic — and 90 minutes later I’ve built a full framework, sales asset, or chapter for my book.
Clarity isn’t found.
It’s externalised.
3. Output Leverage
One big thing a day — and GPT helps me ship it.
I don’t wait for inspiration.
I load up a transcript, reflect, scaffold, and build.
100% of my content for the last two months has been AI-assisted — in my voice, from my thoughts, using my frameworks.
This isn’t automation.
It’s accelerated authorship.
4. Recursive Learning
This is the wildest one.
I now learn how I think by watching how GPT reflects it back.
I’ll write something.
It mirrors it.
I realise: That wasn’t what I meant.
I clarify.
Now we’re both smarter.
It’s like sharpening a knife by running it against itself.
And the feedback loop just keeps getting tighter.
I’ve been using this to train, build, write, and make decisions.
But here’s the deeper thing:
AI doesn’t just scale what you produce.
It scales who you are.
And that’s the meta-skill most people aren’t even thinking about yet.
What do you think? I thinnk it’s wild.
Let me know.
Edit Added: Yes, I am seeing a therapist at the same time I’m doing this, and I share everything with them.
I’ve walked them through the whole process step by step sk they are aware. They are also one of the best in the world.
I believe mental health is exactly like physical health. You must maintain it consistently over time, not just “going to see the doctor” when shit hits the fan.
You can’t bandaid your way through mental health issue with cold showers and saunas.
Ok rant over.
Also AI didn’t write this. It was me.
And if you don’t believe me?
Ask AI lol
5️⃣ The Power of Opposite Experiments – David Heinemeier Hansson
Have you thought about doing the opposite of whatever you’re doing or considering? It’s a really helpful way to test your assumptions and your values. What does the opposite look like, how would it work?
It’s so easy to get stuck in a grove of what works, what you believe to be right. But helpful assumptions have a half-life, just like facts. And it’s ever so easy to miss the shift when circumstances change, if you’re not regularly stress testing your core beliefs.
That doesn’t mean you’re just a flag in the wind, blowing whichever way. But it does mean having enough intellectual humility and creative flexibility to consider that what you believe to be true about your business, about your team, about your technology might not be so.
We did this a while back with full-time managers. We’d be working for nearly two decades without any, but exactly because it’d been so long, we were drawn to try the opposite, just to see what we might have missed. So we did. Hired a few full-time managers to help us test that assumption for a few years.
In the end, we decided that our “manager of one” culture worked better, but it wasn’t a given at the outset. To try the opposite, you really have to believe that you might have been wrong.
Because you’re wrong about something. I guarantee it. We all are.
6️⃣ When AI Buys for You (Checkout Extinction?) – Simon Taylor
Google just killed the checkout page 😦
At Google I/O, they just announced “agentic checkout” – letting users complete purchases *directly within search results.*
This could be a genuine existential threat to every step in the payments value chain.
Here’s why this changes everything 👇
1. The Fintech arms race just accelerated
This is no coincidence:
• OpenAI hired Instacart CEO Fidji Simo for consumer operations
• Perplexity embedded Stripe within its chatbot
• Visa, Mastercard and PayPal announced agentic commerce services in April
Google’s response? Gemini 2.5 (their most advanced AI) will power checkout directly in search.
The battle for who owns the moment before, during and after payment has begun.
2. The checkout page is dying
For decades, merchants optimized checkout pages for conversion:
• A/B tests on button colors
• Reducing form fields
• One-click purchasing
• Cart abandonment emails
Now Google’s agentic checkout could make all that irrelevant.
The agent can even “pay autonomously” – removing humans entirely from the payment flow.
Merchants will need entirely new optimization strategies.
3. The fraud prevention nightmare begins
When Google’s AI completes transactions:
• Who handles fraudulent purchases?
• What happens when products don’t match descriptions?
• How do you validate customer identity?
• Who owns risk management?
Current fraud tools are built for human behaviors, not AI agents acting on behalf of humans.
Every fraud model needs retraining – FAST.
We need a directory for Agents and network tokens (whitepaper coming soon on this)
4. The bigger fintech strategy is clear
Google is transforming “search into a big AI chatbot” with:
• Shopping features in search
• Virtual try-ons with your own photos
• Price tracking with notifications
• Agentic checkout in “a few months”
• Integration with your Gmail, Docs, and Calendar
My takeaway.
The first platform to make agentic commerce seamless wins the next decade.
Every Fintech CEO should be in emergency planning mode right now.
• Payment providers: How will you integrate with Google’s system?
• Merchant acquirers: How will you manage these new flows?
• Checkout optimizers: What’s your new value proposition?
• Risk platforms: How will you adapt your models?
The future of advertising was always commerce.
The future of commerce is loyalty and data.
AI Agents could link all of those.
7️⃣ Why REAL Creatives Still Matter – R.J. Abbott
The biggest lie AI has told us?
“Everyone is creative now.”
False.
Anyone can create. Always could.
But most people won’t.
They never have.
⸻
From Mesolithic cave paintings to Michelangelo to Midjourney;
Creation has always been part of the human existence.
What’s changed isn’t access.
It’s willingness.
⸻
Society doesn’t discourage creativity by accident.
It brands it as weird. As strange.
Unstable.
Non-essential.
And that’s exactly why creatives have been denied a seat at the table, especially in tech.
Because their value isn’t quantifiable.
Their ideas aren’t always scalable.
So they get labeled as a “nice to have,” not a necessity.
We as creatives often point to Steve Jobs as our patron saint,
proof that design and taste can reshape industries.
But here’s the painful truth:
Tech doesn’t see Jobs as inspiration.
They see him as an outlier.
A bug, not a potential feature.
Unrepeatable. Untouchable.
A fluke within the system, not the formula.
⸻
To most industries, creativity isn’t considered a gift. It’s a threat to systems that fear the subjective.
That’s why it’s been dismissed.
But it’s also why it matters more than ever.
⸻
Now we’re told AI has unlocked creativity for the masses.
But remixing anime, mashing action figures, prompting ChatGPT for a poem.
That’s not creating.
That’s asking.
It’s participation, not invention.
Commissioning Picasso for a painting doesn’t make you a painter, and it certainly doesn’t make you Picasso.
It makes you a patron.
Prompting AI is no different.
⸻
If AI is the paintbrush,
most people are still afraid to pick it up,
because creating means exposing yourself.
And that’s what they’ve been trained not to do.
⸻
True creativity demands more.
More risk.
More discovery.
More taste.
More you.
It’s not about the tool.
It’s about your ability to go somewhere no one asked you to go.
And return with something no one knew they needed.
⸻
That’s the difference.
Not between artists and non-artists.
But between those who consume…
And those who create without permission.
⸻
AI won’t spark a creative revolution.
It’ll reveal how few people were ever willing to risk being misunderstood.
⸻
Real creatives aren’t weird.
They’re just early.
And now, the world finally needs them.
8️⃣ Universes We Never Visit – Shashank Sharma
Multiverse & The Architecture of Choice
In 1957, a young physicist named Hugh Everett proposed an idea so radical that even his mentor, the legendary John Wheeler, hesitated to support it. Everett suggested that every quantum event doesn’t just resolve into one outcome but splits the universe into all possible outcomes simultaneously.
This became the Many-Worlds Interpretation of quantum mechanics.
It means this: every time you make a choice, whether to text someone, to say yes, to walk into that room or stay silent, you’re not just choosing a path. You’re birthing parallel realities. In one, you said no. In another, you left early. In a third, you never met the person who changed everything.
And yet, you only get to live one thread. One life. One version.
I often wonder what would have happened if I studied law instead of physics and marketing. I love the idea of it. The architecture of arguments, the ritual of language, the power of interpretation. In another timeline, I’m probably in a courtroom, debating constitutional nuance with a fire I never got to explore here. That version of me exists somewhere, even if I never get to meet him.
Now let’s pause. Because this is no longer just physics. It’s philosophy, a theory that describes regret.
Most people live haunted by counterfactuals. What if I’d taken that offer? What if I hadn’t walked away? What if I’d said what I really felt? These echoes of parallel lives are versions of you that exist in imagination, if not in space-time.
Quantum physics, at its core, is the study of uncertainty. At the microscopic level, the world is probabilistic. Electrons smear across possibilities. Particles express a range of potential until you look, until you measure.
Life mirrors this.
You don’t always know what the right choice is. You don’t get certainty. You get a wave function. A cloud of options. And the act of living, of choosing, collapses that wave into one path.
That’s why people freeze. They’re afraid that choosing one thing kills every other possibility. And they’re right. It does. But the wave must collapse. Stalling is not safety but decay.
Science, for all its logic, is full of heartbreak.
It tells you that nothing is fully knowable, not even yourself. It tells you that the world isn’t built on certainty, but on odds. It tells you that entropy wins, eventually. That time moves in one direction. That the most fundamental truths are not concrete, but probabilistic.
But science also whispers something else. That you’re not here by accident. You are the result of a million quantum events that could have gone differently but didn’t. You are the one timeline that survived the collapse. You are a consequence of possibility, sharpened into reality.
The question isn’t what if I had chosen differently?
The real question is now that I have, what will I make of this universe I’m in?
Because in this one, this fragile, fleeting, collapsing timeline, you still get to choose what happens next.
9️⃣ BONUS: Inspiration is a moment, not a future – Gaetan Portaels
Well, you can find this one HERE.