The hidden ChatGPT setup powering all my writing
I fed ChatGPT everything I’ve ever highlighted. The results? Game changing
“The person who writes clearly thinks clearly.”
— William Zinsser, On Writing Well
For years, I wrote by instinct.
I had a solid sense of who my audience was.
I read a lot. I highlighted what resonated.
And when it was time to write? I’d trust my gut.
But instinct has a ceiling.
It helps you write something good.
But it doesn’t guarantee you’ll write something that lands. Something that gets the “That’s exactly how I feel” comments.
Something that turns readers into leads.
That changed the moment I connected my Readwise highlights to ChatGPT.
Not to come up with more content ideas.
But to write content that speaks directly to my audience’s world—with more clarity, credibility, and conversion power than ever before.
Why Most Content Doesn’t Land
Here’s the problem with how most creators and freelancers write content:
It’s too general
It’s written from memory
It’s driven by what they want to say—not what their audience needs to hear
Even if you have a clear set of avatars (like I do), it’s hard to consistently write to them—especially when you’re juggling multiple projects or client voices.
And when you’re working on behalf of a client, the pressure’s even higher. You need to:
Show you understand the end customer
Write with insight, not fluff
Increase engagement and conversion—not just impressions
That’s where this setup comes in.
The Setup: Readwise + ChatGPT = Message–Market Fit
This isn’t some official integration.
It’s a system I built using:
Readwise, to store all my book, article, and web highlights
ChatGPT Pro, to access those highlights and use them as source material for audience-specific writing
I simply:
Export my Readwise highlights (by book or theme)
Upload them into ChatGPT
Prompt ChatGPT based on the avatar I’m writing for
Here’s the magic:
ChatGPT automatically categorises my highlights into themes—like pricing, productivity, mindset, or burnout—and maps them to whatever audience I specify.
So when I say:
“Write a post for solo agency founders who feel stuck undercharging. Use my highlights on pricing, value creation and self-worth.”
It delivers something that doesn’t just fill a slot on the content calendar.
It resonates. It converts. It makes people reply, click, comment, or book a call.
This Isn’t About More Content. It’s About Better Outcomes.
Before this setup, I’d often get stuck in idea-hunting mode.
Now I spend zero time trying to “come up with” content—and all my time dialling it in to the exact people I’m speaking to.
That’s the real value here.
This system lets me:
Write directly to my audience’s frustrations and desires
Tailor tone, language, and examples to each avatar
Build trust faster (for myself and my clients)
Improve click-through, engagement, and conversion rates
Sound like an expert—because I’m using my own knowledge base
Why It Works So Well for My Client Work
I ghostwrite content for founders, strategists, and agencies. That means switching between voices and goals daily.
Using this Readwise + ChatGPT system means:
I can write LinkedIn content that nails message–market fit
I can produce newsletters that speak to customer pain points with real authority
I can pull in quotes, stats, and anecdotes that actually back up what we’re saying
Instead of fluff-filled marketing content, I deliver substance that sounds smart and feels personal—even when the client’s audience is completely different to mine.
This isn’t about “more content.”
It’s about creating the right content—faster, more credibly, and at scale.
What the Workflow Looks Like
Step 1: Export from Readwise
Pull your saved highlights by book, article, or tag. I do this weekly.
Step 2: Upload to ChatGPT
Upload the text into a chat thread or GPT. It immediately identifies key themes and topics.
Step 3: Prompt by Avatar
Examples:
“Use my highlights on pricing and scarcity to write a LinkedIn post for agency owners who undercharge.”
“Create a newsletter outline for CMOs overwhelmed by AI tools. Use highlights tagged ‘focus,’ ‘decision-making,’ and ‘value’.”
“Give me headline options using my own language on productivity for solopreneurs.”
Every single time, the output is more tailored—and more effective—than what I used to write on instinct.
Want to Try It Yourself?
If you haven’t used Readwise before, now’s the time.
You can get a 60-day free trial with my affiliate link - that’s twice as long as the standard 30 day trial at no extra cost to you.
What you get:
All your highlights (from Kindle, PDFs, Twitter, Pocket etc) in one place
Daily review emails to surface your best thinking
Simple export options to feed into ChatGPT
A personal knowledge base that improves every single thing you write
I only promote tools I use daily. Readwise is the cornerstone of this system—and this article. In fact, it is the first app that I recommend to anyone working online.
Final Thought: Resonance Wins
You don’t need more ideas.
You need more resonance.
More of the “Wow this is exactly what I needed” messages.
More of the “I’ve never seen it explained this clearly” replies.
More content that feels like it was written just for them.
This system helps you do that. Not with fluff. Not with guesswork but with your own curated knowledge. Targeted to your audience.
Delivered by the best writing partner you’ve ever had: you, plus ChatGPT.
Coming next week:
I’ll walk you through my exact prompt stack for writing a month of high-performing client content—tailored by avatar, objective, and theme.
Until then: write to resonate, not to fill space.
Simon
Love this workflow. I do something similar in Tana where I have a customgpt set up on my readwise notes.
Have you tried out Claude’s Readwise MCP? It would cut out the export step and you could chat directly with any highlights.