TRLW: #010: AI is a genius, cocky, scared kid

Welcome to The Road Less Written—your monthly writing guide to creating stand-out content that resonates.

In this issue, we’ll explore:

• Why AI is a genius, cocky, scared kid

• Junk food vs. fine dining content 

• Fine dining content takes time 

• How to write uncommon content 

• How I can help

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A genius, cocky, scared kid

(Credit to Eddie Shleyner in Very Good Copy for this idea):

In Good Will Hunting (1997), Robin Williams plays a therapist helping a troubled genius, Will Hunting. In one powerful scene, Williams delivers this unforgettable monologue:

“So if I asked you about art, you'd probably give me the skinny on every art book ever written…But I bet you can't tell me what it smells like in the Sistine Chapel…

If I asked you about women, you'd probably give me a syllabus of your personal favorites…But you can't tell me what it feels like to wake up next to a woman and feel truly happy..."

"I don't see an intelligent, confident man. I see a cocky, scared kid."

AI is the same—brilliant at recall but lacks your lived experience to connect the dots. It lacks nuance and depth. It’s never smelled the Sistine Chapel or woken up next to someone and felt truly happy.

Like Will Hunting, Al is a genius, cocky, scared kid.

The “A” means Artificial

In Walden (1854), Henry David Thoreau warned of society’s tendency to trade complex, nuanced ideas for basic, simplified thoughts. “We are in a period of mental and intellectual decline,” he wrote—a sentiment that feels just as relevant today.

Scroll through LinkedIn, and you’ll see it: artificial noise. Uninspiring ideas. Generic style. Little substance. It’s “junk food” content. Consume too much, and you’re left oversaturated but understimulated—damaging both your intellect and mental health.

Investor Paul Graham recently echoed this in his blog:

“In preindustrial times most people's jobs made them strong. Now if you want to be strong, you work out. So there are still strong people, but only those who choose to be. It will be the same with writing. There will still be smart people, but only those who choose to be.”

This is your opportunity to stand out and choose to stay smart. My clients have spent 10-20 years mastering their craft. Their earned insights allow them to create “fine dining” content—substantial, nuanced, and deeply satisfying for their reader.

Fine dining content takes time

Recently, I wrote 5 LinkedIn posts for a client and tested AI prompts to edit them.

• The tone was off.

• The depth was shallow.

• The audience wouldn't resonate.

So I manually edited the posts.

• The client’s voice stayed intact.

• The nuance and key details remained.

• The posts resonated with ideal clients.

Here’s why the manual version worked:

1. I got crystal clear on the client’s ideal audience.

2. I understood their offer inside out.

3. I pulled the best insights from our interview to hit 1 + 2.

The real work happens before writing—it’s in the thinking, the preparation, and the strategy. It takes time, but the results speak for themselves.

Publishing the AI-edited version would’ve hurt the client’s credibility. A ghostwriter doesn’t just write for you—they handle your reputation. So choose wisely.

Be uncommon

Don’t ignore AI—it’s evolving fast, and you have to evolve with it. One day, it won’t be the cocky, scared kid anymore. So sticking to old ways is like choosing a horse and cart while everyone else is driving cars.

I use AI tools like ChatGPT and Claude daily. They’re fantastic thinking partners and assistants. For example, I use ChatGPT to clean up interview transcripts while keeping the client’s voice intact. What used to take me hours (pre-AI) now takes minutes. 

But here’s the catch: It’s a tool, not a magic bullet. Tools don’t guarantee ability. Give me a brick and I can’t build a house. And the more I use AI, the dumber and more dependent I feel. That’s why I make it a point to keep my thinking sharp:

1. Limit news and social media consumption: It adds to brain rot and scattered thoughts. As #1 NYT bestselling author James Clear says, “The more you create, the more powerful you become. The more you consume, the more powerful others become.”

2. Walk outside at sunrise or sunset (no headphones): Let nature inspire clarity, creativity, and calm.

3. Challenge your brain with mental games: My son is currently teaching me chess. Getting destroyed in every match hurts my brain, but it’s making me sharper.

4. Do mind-body connection activities: Jiu Jitsu, saunas, ice baths, hot yoga, lifting barefoot outside, box breathing, and meditation all keep me grounded.

5. Read books for fresh perspectives and reflection: Current read: The Untethered Soul. Next up: Reinventing Your Life, which explores the self-imposed “lifetraps” I covered in my last newsletter.

6. Capture ideas and solved problems in Apple Notes: The best content comes from earned experiences.

7. Journal daily: Last year, I filled an entire Moleskine with reflections and insights. Free writing refines my thinking.

8. Speak into Otter for transcription: When inspiration strikes, speaking out ideas can unlock excellent ideas.

9. Listen to 528 Hz music: Known for its calming and focus-enhancing effects, it’s my go-to tool for productive flow.

Writing is a craft. AI can assist, but your unique voice and experience will make your content extraordinary. 

As Paul Graham said: “Writing is thinking. In fact, there’s a kind of thinking that can only be done by writing.”

So keep writing, keep thinking, and keep connecting.

Until next month,

Steve “Clear Thinking” Costello

How I can help

1. Ghostwriting (5M+ views driven) →  I craft 1 month’s worth of LinkedIn posts and a newsletter from a single interview—designed to attract high-quality leads.

2. Your Head of Content (1.5M+ words edited since 2014) → I edit the posts you write to sharpen your message, amplify your voice, and resonate with your ideal audience—helping you attract high-quality leads.

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