Writing on a thinking typewriter

Have you tried hiring AI to improve your writing? Here's a structured process to get feedback, make revisions, and maintain a human tone. Read: "Everything Starts Out Looking Like a Toy" #250

May 12, 2025

Hi, I’m Greg 👋! I write weekly product essays, including system “handshakes”, the expectations for workflow, and the jobs to be done for data. What is Data Operations? was the first post in the series.

First, THANK YOU for reading! This is the 250th issue …

This week’s toy: have you ever wanted to drive an F1 car? How about a complete scale model F1 car, made of LEGO! Yep, they exist, and go 12 MPH. I’m confident I can make the necessary F1 turns at that speed. Also, if the car breaks down, I’ll be able to add almost any part to it immediately.

Edition 250 of this newsletter is here - it’s May 12, 2025.

Thanks for reading! Let me know if there’s a topic you’d like me to cover.

The Big Idea

A short long-form essay about data things

⚙️ Writing on a thinking typewriter

Writing in the age of AI reminds me of the first word processors (and typewriters). These magical boxes did … exactly what you wanted them to do and more. Instead of using correction fluid or tape to lift the ink off the paper, you saw digital text on a monochrome screen.

[DELETE] and [BACKSPACE] became things you did instead of just typing the letters one after another and physically twisting the dial of the carriage return to raise the paper so that you could fit one more line on the page. Shifting the mental model from paper to bits was an important step in the age of writing on a computer.

Immediately, you could rearrange entire paragraphs of your writing and move them to another point in the essay. It’s hard for people who grew up in the age of the iPhone to realize this, but even simple functions like spell checking felt like magic at one time.

So when you start thinking about writing in the age of AI, it’s reasonable to wonder: what’s it like to write on a thinking typewriter?

Like the leap from paper to bits, we’re making the leap from local to networked and distributed thinking. In a way, this is like using a cloud service like Google Docs, where you write in your own environment and gain the advantages of saas tooling and don’t worry about local software.

There’s something different here. You are now writing (and collaborating with) a system that compounds knowledge.

Because AI tools have context, memory, and tools, they have the opportunity to function not only as an editor during a single session, but also over time as a true collaborator that learns its job is to improve your writing while maintaining your style and tone.

Getting comfortable with an uncomfortable metaphor

Why would I want to collaborate with an AI tool?

It’s ok! Not everyone feels comfortable with this idea. But when you start going down that road of “don’t use AI for stuff”, I’d ask you some questions.

Do you drive a manual shift car?
Use a film camera with manual focus?
Take the stairs when an elevator is available?

You might take pains to avoid automation — I don’t want to suggest you should stop.

When we adopt new technologies, certain things are easier for more people and we open up new capabilities that didn’t exist before.

Other jobs and capabilities will be different and might disappear. Consider the occupations of coal miners, elevator operators, and switchboard operators as examples of work that doesn’t exist today. The idea of writing natural language to prompt a cloud window to write prose would sound like science fiction to many of those people.

It’s not going to slow down.

In the future, we will talk more to machines (or machine processes) to do work. These proxies or agents may seem more human over time. We might not have “superintelligence” any time soon (or maybe ever). But we will continue to become cyborgs and rely more on machine services to expand the capacity of what we can do electronically.

What is Vibewriting?

To force myself to get comfortable with experimenting more often with new tools and technologies, I decided to try “vibewriting”. It’s the idea that you can start having a conversation with tools to drive a writing process while maintaining a human touch and tone.

Can you apply the “vibecoding” approach to writing? One of the things that doesn’t go well in vibecoding is the tendency for inexperienced coders to end up in logical loops as the software answers the same question non-deterministically.

Does the same thing happen when you use AI as a writing partner?

Blindly accepting the content produced by AI during editing can create the exact same problems as AI coding. If you need something more than the equivalent of a syntax check on a function call, you’re going to need to think about your prose a bit. But it’s a huge time saver to iterate rapidly and propels you to get more done quickly.

You were going to start with a template anyway, right?

Vibewriting is more than just using AI to help with your writing. Think of it as having a writing partner who's always ready to bounce ideas around, help you break through blocks, and refine your thoughts - but one who never gets tired or needs a coffee break.

Using AI tools to structure a writing process and move through it faster reminds you that writing, like other creative pursuits, demands revision.

And that’s the thing that AI vibewriting makes a whole lot easier. You are expecting to revise your writing multiple times. If you’re not used to crafting and improving your writing, this will help you practice something you should have been doing all along.

Finding Your Writing Path

Let's acknowledge something important. There is no one "right" way to write. Some writers find their best work comes from:

Solitary reflection and careful crafting
Collaborative brainstorming with human partners
Free-writing and stream-of-consciousness
Structured outlines and methodical development

If you find your voice through traditional writing methods, that's perfect. This idea is about offering another tool in your writing toolkit.

Let’s talk about the functional steps to use AI tools to help you write with an AI collaborator. Having a structured process and checkpoints for your writing will produce better results than letting the chatbot or the tool do all of the work.

One way to collaborate with AI

When I collaborate with AI, I start with a random collection of ideas and end with a draft for an essay or other work I feel comfortable sharing with other people.

During the process, I ask AI to improve the structure and organization of my work. But the end product still goes through a significant editing pass where I rewrite in a single session or two to blend the content and coalesce it into my writing “voice”.

Here are the steps of the process.

Step 1: Start with Raw Notes

The notes stage is a mess. It might start with a Note on my phone, a few ideas scribbled on a pad, or a single idea. I use this part of the process to stack ideas together and don’t worry about the structure or relatedness of the concepts.

When I collaborate with AI, I create a new markdown file and dump in my initial thoughts:

- personal experience with AI writing
- different writing styles
- the collaborative process
- practical commands
- structure and flow
- making it your own
- real examples

When we’re done, I have a new-draft.md file that has the text we’re discussing.

(We use a Markdown file because editors like Cursor can read this format easily and change files on your behalf.)

Step 2: Start the Conversation with AI

This is where things get creative. In Cursor, you can start a chat with any file in your codebase (it’s a fork of Microsoft VS Code). You don’t need to be using source control to try this process out and talk to your notes document.

If you’ve used Chatbots like Claude, Gemini, or ChatGPT, this part should seem familiar. But there is a key difference. You are establishing a very specific context and instructions with your chat. In addition, you can go back and forth with the bot or ask it to create a formal plan based on your writing and editing rules.

For example, you might want your writing to follow APA Guidelines. That might mean asking the bot to read a URL or giving it a different text file with specific instructions. When you do this, you are in effect creating a kind of AI agent who checks your grammar.

When you start your chat, it might look like this one:

Me: I'm working on a piece about writing with AI. I want to call it "vibewriting" - the idea of establishing a creative flow with an AI editor. Here are my initial thoughts. Can you help me think through the structure?

AI: I like the "vibewriting" concept - it captures the collaborative, creative nature of the process. We could structure this as:

1. Your personal discovery of this approach

2. What vibewriting is and how it differs from traditional AI writing

3. The collaborative process in action

4. Practical tips and commands

5. Real-world examples

Would you like to explore any of these angles first?

Me: Yes, I think starting with the personal story would help readers connect with the idea. Then we can build out the practical aspects.

Or it might look very different. The goal here is to use a structured series of questions and prompts to improve your content and move it from a few ideas into a topic you want to pursue. If you’re not feeling strongly about your idea, return to the drawing board.

Why do this? To move from a few thoughts to a first draft for review by the “Editor”.

Step 3: Get Editorial Feedback

Your AI editor can also give you feedback with a different lens, such as a writing coach. One tactic that helps your writing is to keep interrogating it with a tireless editor.

I ask the AI to review the draft from different perspectives.

Me: Can you read this as a writing coach and tell me what's working and what needs improvement?

AI: As a writing coach, I'd say:

- The personal story creates a strong connection

- The "vibewriting" concept is clear and engaging

- Could use more specific examples of the back-and-forth process

- The commands section feels a bit disconnected from the narrative

Would you like me to suggest specific improvements for any of these areas?

If you’re looking for specific tactics, AI editors can also help you with the practical mechanics of your writing in different areas.

Prompts for Style and Tone

Editing for consistent style and tone will help your work sound better. Here are a few prompts that will help.

"Make this more conversational, like I'm talking to a friend"

"Add some personality to this section"

"Make it sound more excited about [topic]"

"Tone down the formality here"

"Add some humor to lighten the mood"

Improve Flow and Structure

You might feel stuck in the middle of your draft. Fortunately, AI is skilled at assessing the logical flow of your writing.

"Help me transition smoothly between these ideas"

"Break this long paragraph into more digestible chunks"

"Connect these two thoughts more naturally"

"Add a hook to grab attention at the start"

"Wrap this up with a strong conclusion"

Drive Clarity and Impact

Your AI editor can help you get out of your own head, literally. Here are a few prompts to see if you’re making sense.

"Simplify this complex idea"

"Make this more engaging for [target audience]"

"Add a real-world example to illustrate this point"

"Strengthen this argument with supporting evidence"

"Cut the fluff and get to the point"

Make a Creative Boost

Finally, it can be great to get a creative spark. AI is good at suggesting ideas.

"Suggest three different ways to approach this topic"

"Help me find a fresh angle on this idea"

"Add some creative metaphors to explain this concept"

"Make this more vivid with sensory details"

"Turn this dry fact into an engaging story"

Like any good editorial feedback, you might want to adapt it, or you might ignore it completely. The beauty of using Cursor for this conversation is that each change is delivered to you to approve or deny. You don’t need to let the AI change everything, or anything.

Step 4: Move to Google Docs and Refine

It turns out Google Drive lets you upload a markdown file and format it automatically. That’s the next step in our process, where you upload the file to Google Drive, convert it to a Google Doc, and edit it in the traditional way.

I will read the essay aloud to check the flow, rewrite introductory paragraphs and connecting sentences, and test that the overall tone matches my voice.

This is the traditional “writing” phase, and it’s pretty familiar. Except that you are starting from a much more fully formed draft. In the old writing model, the Google Docs step might take hours. Now it takes much less time to refine the content and get to a fully edited final draft.

And that’s what vibewriting is really about. It’s not about letting AI do all ot the work for you. It’s about having a process that produces better content rapidly and maintains the voice of your writing.

AI editing is a typewriter that does some amazing things. At the same time, you still need to sit down, roll a figurative piece of paper into the typewriter, and put your hands on the keys to make great content.

What’s the takeaway? No technology will create great writing automatically. You can generate the writing with AI, but it won’t sound like you. Use the “Thinking Typewriter” to go through revisions faster and build stronger, more resilient arguments. Then edit it so it sounds like your voice.

Links for Reading and Sharing

These are links that caught my 👀

1/ Building guardrails for AI - It sounds like Pandora’s box (or perhaps, Skynet) to let AI agents loose in your environment. But how different is it, really, than delegating the privileges for certain actions on accounts you control today? We need to be thoughtful about how we build detection and orchestration into the “agent features” of the future so that the contract of what an agent can and cannot do is very clear. One team thinking about this? Arch Gateway is defining a “triage” function to orchestrate AI process.

2/ You can’t fix it all - The next time you think “I should solve that”, read this essay. It’s a very good compilation of reasons why you can’t solve everything, and will remind you that you need to be solving the right problems, not just the one you see in front of your face at this moment.

3/ Travel around the world - Explore the wonders of Google street view. There are some really unexpected things here (make sure you try the random button).

What to do next

Hit reply if you’ve got links to share, data stories, or want to say hello.

The next big thing always starts out being dismissed as a “toy.” - Chris Dixon