How to build a proprietary content engine using your holiday memories

Using AI to translate “non‑work” memories into proprietary strategy your competitors can’t reverse‑engineer.

Joy calls it “play,” Sadness calls it “finally telling the truth about what happened,” and inside out, both are right.

Your camera roll holds more strategy than your analytics dashboard.

I spent my Christmas in Vienna and my New Year’s in the Transylvanian mountains, re-reading Gabriel Liiceanu’s The Păltiniș Diary (a journal of a frozen mountain retreat turned into a school of high-level thinking).

I went for the silence but I came back with a smuggling operation. A lot of memories that could shape my content and product strategy.

The question was, how do I get that feeling past the border control of the internet?

This is a “for fun” edition (and workflow!) about running your holidays and experiences like a field study. You capture raw stimuli first, you dissect the mechanism second, you translate it into principles third, and you ship small experiments fourth.

Let’s go, JOY! (Load the truck, Sadness. We’ve got a border to cross)

🥷Use this when: You need to break out of generic industry patterns by injecting your unique life experiences into your product strategy.

🥷What you’ll need:

• Access to your recent camera roll or personal journal.

• A raw list of specific, non-business sensory memories.

• An LLM window ready for prompt chaining.

🥷What you’ll get:

• A structured database of emotional mechanics.

• A set of proprietary strategic principles derived from real life.

• 3 distinct, ship-ready experiments (content, product, distribution).

But first, the 60-second Smuggler Challenge

Before we go deeper, I want YOU to try a quick experiment and sneak one piece of raw humanity past the AI sensors.

Copy and paste this prompt into a LLM right now with just ONE weird thing you saw during your holidays:

I just got back from my holiday. Here is one specific, weird, non-business thing I saw: [INSERT ONE MEMORY].

Act as a Smuggler Agent and Strategic Architect. Your job is to find the 'Signal' in this memory that my competitors are missing. Based on this sensory detail, identify 3 'Blue Ocean' positioning angles I can use to differentiate my brand. For each angle, explain:

1. The Counter-Narrative. What 'standard' industry belief does this memory disprove?
2. The Aesthetic Moat. How can I use the 'vibe' of this memory to make my brand voice un-copyable?
3. The High-Status Shift: How does this specific detail make my audience see me as an Architect rather than a Grunt?

Reply with the memory and the most unique principle it gave you (I’ll feature you in next Monday’s edition!) Let’s see who has the weirdest “Signal” in their holiday.

The Smuggler Agent works by literally smuggling your raw, chaotic memories past the border control of your professional filter and inject them directly into your product strategy.

Let’s do it together.

₊⊹ Step 1: Gather the chaos in under 10 mins

The goal is to capture raw stimuli over polished reflections.

Think tiny, specific things.

‼️Do not let the AI hallucinate your inputs. Stop now and write down 5 specific, messy things you saw this week. If you skip this, your results will be generic trash.

Open your photo app and look at your recent ones before getting fancy with prompts.

Choose some of these memories and structure a list of 20 short bullets.

My list included:

• Hiking through the Döbling vineyards between both heavy winter snow and bright orange autumn leaves;

• Booking a stay in the “Tower House” in Sibiu completely by accident only to realize that I was on the exact same street as my aunt’s holiday home;

• Watching the violinist at the Christmas concert in Karlskirche take a sharp, audible breath before every solo.

Work with what you have, even if you don’t hit 20 items.

Then use this prompt:

You are a “Smuggler Agent” that helps founders turn life experiences into business experiments. Your job is to take raw, chaotic human memories and package them for transport into the business world.

Here is a raw list of moments and memories from my life:

[YOUR LIST OF RAW MOMENTS]

Normalize them into a table with these columns:

id (number them)

short label (3–5 words)

1–2 sentence description (keep concrete and sensory)

context type (e.g., concert, architecture, street, food, interaction)

Return ONLY the table in markdown format.

Here were my results:

This practice builds your instinct for noticing. Now we crack them open.

₊⊹ Step 2: Dissect the feeling

Once you’ve captured your chaos, it’s time to find out what made it stick.

The Smuggler Agent now breaks each moment into its sensory and emotional components. Our goal is to figure out what caused the feeling.

If you can identify the mechanism that created a feeling of awe or trust in a holiday moment, you can reassemble that same logic in a sales email.

Use this prompt:

You are now operating in Layer 1: Sensory Deconstruction.

For each row in this table of holiday moments, extract:

dominant sense(s) (sight, sound, smell, touch, taste)

perceived pace (sudden / slow-burn / stop-start / rhythmic / static)

contrast (what is this moment contrasted against?)

tension (what creates uncertainty, discomfort, or anticipation?)

relief or resolution (what creates closure, calm, or clarity?)

abundance vs. scarcity signals (what feels “too much”? what feels “almost nothing”?)

dominant emotion in the observer (e.g., awe, annoyance, curiosity, nostalgia)

Return a new table, preserving the original id and short label.

Be honest about negative emotions. Sadness is often a better smuggler than Joy.

What I got was:

Okay, looking at this output, Principle #3 is actually usable immediately.

And it reminds me of this post I wrote with Sam Illingworth on building deliberate pauses when working with AI.

Everything worth keeping happens between the prompts

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The AI identified that the value wasn’t the music itself, but the signal that effort was about to happen. In business terms, this means my blog posts can sometimes be too polished. I just deliver the “music” (the answer).

I need to put the “breath” back in, showing the messy research or the failed attempts before I give the solution.

₊⊹ Step 3: Extract the principle

Layer 2 converts those sensory components into abstract, reusable strategic principles.

Use this prompt:

You are now operating in Layer 2: Strategic Principle Translation.

Given this table of deconstructed holiday moments, do the following:

For each row, infer 1–2 strategic principles that could apply to marketing, product design, or customer experience.

Make them general, e.g.,

“Delayed resolution builds anticipation.”

“Sensory overload followed by simplicity creates relief and trust.”

“Clear thresholds signal that a new chapter has started.”

Format as a table:

id (from original item)

short label

principle 1 (short name + 1–2 sentence explanation)

optional principle 2 (if clearly distinct)

Avoid generic clichés; ground each principle in the specifics of the moment.

Here is my output:

These are so interesting! Principle #1 (Visual Dissonance) is the most actionable for newsletter headers.

The table highlights that “Nice View” is not really a strategy. We want conflict.

If you apply this to your newsletter visuals: Don’t just put a robot. Put a robot in a context where it absolutely doesn’t belong (like a Renaissance painting or a messy kitchen).

I know AI Meets Girlboss would LOVE this because she’s the queen of visuals! 😁

One Visual Decision Took Me From 64 to 200 Substack Subscribers

When you read through your principles, ask: “Which of these feel yellow-orb obvious?” (Joy’s favorites) and “Which feel blue-orb honest?” (Sadness’s favorites).

You’ve got the rules now. Time to make them dance.

₊⊹ Step 4: Make it move

Three micro-experiments across PRODUCT, CONTENT and DISTRIBUTION.

Finally, we push those principles towards action using this prompt:

You are now operating in Layer 3: Applied Experiments.

Given this table of strategic principles, propose experiments.

For EACH principle, suggest:

1 content experiment (e.g., a specific newsletter segment, landing page variation, or social thread)

1 product/offer experiment (e.g., a feature tweak, packaging change, onboarding flow adjustment)

1 distribution/timing experiment (e.g., changing when/where/how this is published or delivered)

Each experiment should:

Clearly embody the principle.

Be small enough to ship in 1–3 days.

Include a simple measurable result or target outcome.

So, I got 3 experiment bundles myself, and this was my favorite one:

Experiments for Principle 1: Visual Dissonance (The Snow/Leaves Clash)

• Content: The “Glitch” Header. For the next newsletter, create a header image that combines two clashing aesthetics (e.g., a pixel-art robot sitting in a hyper-realistic, oil-painted Renaissance room).

  • Metric: Click-through rate (CTR) vs. your average.

• Product: The “Messy” Checkout. Change your checkout or signup success message from a standard “Success!” green box to a handwritten, slightly messy “Post-it note” style graphic overlaying the clean UI.

  • Metric: Screenshot/share rate (do people talk about the nice UI?).

• Distribution: The “Wrong Channel” Drop. Publish a text-heavy, serious strategy piece on a visual-only platform (like Instagram Stories or TikTok text mode) or a meme-heavy thread on LinkedIn.

  • Metric: Engagement rate (comments) from people surprised by the format break.

Of the three, I always already implement the Content one, and also the Product one as I like to go beyond the standard “thank you page”. The Distribution one was a bit weird but if I were on multiple platforms, I’d probably test it just for fun.

⤷ TWO TRICKS FOR BETTER RESULTS:

Here are 2 pieces of advice so you can nail your results even further:

1. Let Joy narrow the scope. This workflow will give you “Strategy pieces” from the results. Some might not apply to you, like the distribution one for me. Narrow this down by asking AI to be specific only to one of them (PRODUCT, CONTENT, DISTRIBUTION).

2. Let Sadness sharpen the stakes. Ask: “Where did this memory carry loss, fear, disappointment, or longing?” Those are often the places where your audience is secretly stuck too. If you want to incorporate some of these memories and findings into your actual newsletter content, use this prompt:

Please give me some ideas on how to implement some of these experiences into my newsletter content pieces (written only). My topic is: X, my niche is: Y.

I want to see what you’re smuggling across the border. Give me the ONE weird, useful and strategic principle you got from this workflow (or from the 60-second challenge at the beginning of the post).

I’ll feature the most interesting ones in next week’s edition. Let’s see who has the weirdest proprietary advantage this week.

To my favorite smugglers,

Chief 🤖 at ROBOTS ATE MY HOMEWORK

🚠 The lift to the top doesn’t stop here. Here are a few more high-altitude strategies to help you see the patterns in your business:

Snowfall over the AI factory floor (and 25 prompts to clean your slate)

Build your content like a movie trailer the brain can’t walk away from

Reverse-engineer yourself before you train your AI

Autocomplete is stealing your homework