From Clutter to Clarity: Streamlining the Newsletter with AI

For years, my newsletter has been a cornerstone of my work—almost 400 issues filled with insights, curated content, and reflections. However, as I began migrating all my ideas and projects into a unified markdown-based system within Obsidian, the scale of the task felt daunting. My goal was not just to archive these newsletters but to give them a second life as part of a connected digital garden. To do this, I turned to generative AI tools like ChatGPT, which have proven invaluable in streamlining the process.

Here’s how I tackled the challenge and how AI helped me transform my newsletter from cluttered archives into polished, cohesive resources.

The Process: Cleaning Up 400 Issues

Converting 400 issues of a newsletter to markdown isn’t just about moving text; it’s about reimagining the content for a new medium. My initial step involved using scripts in Node.js to automate the conversion of text from my newsletter platform into markdown files. While this provided a starting point, the output was messy—clunky formatting, unnecessary images, and inconsistent metadata cluttered the files. That’s where ChatGPT came in.

Using ChatGPT, I:

• Streamlined Headers: Each issue’s header was cleaned up and standardized to remove redundant images or unnecessary clutter. I adopted a concise format that included a title, a subtitle, and metadata tags for themes and topics.
• Refined Metadata: I used ChatGPT to suggest tags, categories, and properties for each issue, ensuring that these fields connected the note to broader themes in my digital garden. This has been critical for creating cross-links between notes.
• Simplified Content: While I didn’t want to lose the essence of each issue, ChatGPT helped remove verbose or outdated text and reorganize the core message. The tool provided suggestions for more concise phrasing, which I could accept, reject, or modify.

This combination of Node.js and ChatGPT allowed me to focus my attention on creative decisions rather than repetitive formatting tasks.

How AI Streamlined the Process

Generative AI has become a partner in my workflow, providing:

• Suggestions for Organization: ChatGPT analyzed the themes of each issue and offered ideas for grouping them into categories. This helped me identify overarching themes and create Map of Content (MOC) notes for easy navigation.
• Change Logs: As someone prone to ruminating and revising, I used ChatGPT to create a "changelog" for decisions made during the process. This log has been invaluable for tracking why I made specific changes and ensuring consistency across notes.
• Markdown Refinement: Once converted, markdown files often contained irregularities. ChatGPT reviewed the files, identified areas for cleanup, and suggested uniform formatting rules.

The beauty of this collaboration is that it leaves room for my personal touch. While ChatGPT provides a baseline, I still decide what to include, exclude, or modify. This iterative process ensures that the final product reflects my voice and intentions.

Balancing Automation with a Personal Touch

One of the challenges in using AI for a creative project is balancing efficiency with authenticity. I wanted my newsletter issues to feel human and reflective, not robotic. To achieve this, I:

• Reviewed Every Change: Even when ChatGPT suggested edits, I ensured that each one aligned with the tone and purpose of the original content.
• Added Reflective Elements: Each issue now includes a “Key Takeaways” section and reflection questions. These elements were inspired by AI suggestions but customized to fit my style.
• Connected the Dots: With the help of metadata and cross-links, I’ve woven the newsletter issues into the broader fabric of my digital garden. Readers can explore themes across multiple issues, creating a richer experience.

Not Entirely TL;DR

When I first started my newsletter, it was called TL;DR (Too Long; Didn’t Read). The goal was to create concise, to-the-point content. Over time, I began taking risks and connecting dots between themes each week. As a result, my issues grew longer and more nuanced.

Working with large language models (LLMs) like ChatGPT has added a new dimension to this process. Initially, I appreciated how the AI streamlined my content into bite-sized chunks, removing commentary and the cognitive leaps in my writing. However, as I’ve gone through my 400 issues, I’ve found myself preserving much of my original text, ideas, and connections—even the longer, more reflective passages.

This has led me to question whether the AI is reflecting what readers truly want or if I’m simply being stubborn and out of touch. Still, when I revisit my older content, I remember the thought and time invested in crafting those connections and the space I wanted to create for readers to engage with them. Ultimately, I’ve come to see these passages as valuable content worth archiving and carrying into the digital garden, one plant at a time.

Integrating AI Output into My Knowledge Management System

To maintain clarity and differentiate between AI-generated content and my own writing, I integrated the output from ChatGPT into my personal knowledge management system using code blocks in markdown. Each suggestion, revision, or generated section from ChatGPT was enclosed in triple backticks to clearly identify its origin.

The image below shows how this looks in my notes.

This visual distinction allowed me to review AI contributions more critically and trace how they influenced the final content. Additionally, it provided a clear record of where connections, tags, or insights stemmed from my own analysis versus AI suggestions. This approach not only improved transparency in the process but also ensured that the final notes retained a balance of automation and personal creativity.

Lessons Learned

1. AI as a Collaborator: Generative AI is most effective as a partner, not a replacement. It helped me cut through clutter, but the final product required my judgment.
2. Iteration Matters: The process of refining 400 issues highlighted the importance of iteration. AI helped accelerate the process, but the real magic happened in the review and revision stages.
3. A System for the Future: Beyond cleaning up past issues, this project has set the stage for a more organized future. New newsletter issues are now created directly in markdown, with all the metadata and tags in place from the start.

The Outcome: A Cohesive Digital Garden

Today, my newsletter lives on as part of a dynamic, interconnected system. Each issue is not just a standalone artifact but part of a larger narrative. By leveraging tools like ChatGPT, I’ve turned what felt like an overwhelming project into an opportunity to reflect, organize, and grow.

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For anyone considering a similar journey, my advice is simple: embrace the tools at your disposal, but don’t lose sight of your creative vision. The right balance of automation and personal touch can transform even the most daunting tasks into meaningful work.