The History of My Creativity System

While mapping my inputs and outputs… I realized the tools I used and goals I aimed for shaped my Creativity System over the years.

This section was originally part of an overly long post… but for those of you who interested in the path I have taken to my current strategy… here you go:


I have spent my career working on websites or web applications. A lot of my personal and professional growth is through blog posts and essays… subscribed using RSS and read in a browser or often in Instapaper.

📗 Books

Recently I've been aping Bookworm and making mind maps as I read… turning the standout themes into standalone zettel notes. I have been exporting Kindle highlights/notes using Bookcision manually… but now Obsidian Kindle Highlights handles that for me. (More on all this soon!)

🗒 Meetings

While in meetings, listening to sermons, or even just conversations I'll often have Drafts or my Bullet Journal open, jotting down thoughts.

🚿 Shower Thoughts

Never underestimate shower thoughts. 🤷 More often than not… a new question or line of inquiry will suggest itself in the quiet nothingness of a walk, shower, or workout. If the notion has value… I want to be able to connect and use it later.

Many of my blog posts have started from such a note!


🧠 Thinking

I want to invest in better thinking. Well made notes (especially linked!) have allowed me to have meaningful conversations with my own brain… finding new connections and revisiting old ones.

📖 Bible Study

I've always admired those whose Bibles are dog-eared and covered in marginalia. I've acquired half a dozen collections of notes and highlights across different apps and printed editions… I want to build something more permanent, portable, and searchable.

I'm about six months-ish into this process… and it's starting to bear fruit. When the pastor mentions a passage… I can find every note, highlight, journal entry, or booknote that references that passage. It's hugely powerful, and hopefully over time will reduce the "huh, where did I hear that before?" feeling.

✍️ Writing

I like to write blog posts. I have always toyed with the idea of writing a book someday? 🤷‍♂️

💼 UX Work

In my role as a User Experience Designer I deal with complex context: lost users, UX debt, oral histories, nuances of product surface, operations practices, and more. These product hypotheses and individual user insights don't belong to any single project… so hypertext notes are an awesome tool.


🔐 Data

I need to own my own data and avoid vendor lock-in. I prefer a 0data style application like Obsidian, and an easily portable file format like markdown.

🔨 Tool Investment

I've invested a lot of time in Vim and If you don't use these tools, some of my constraints may not matter, but it's worth noting.

History and Obstacles

Here's the tangled tale of my digital plaintext notes so far. I think it's most helpful to see the things that didn't work, worked for a while… how I got here.

1️⃣ Random plain text.

I started making simple Notepad ++/TextEdit notes at my first job and college.1

2️⃣ Evernote

I flirted with this briefly… but I didn't want to be locked in a walled garden. (I was already investing in vim.)

3️⃣ nvAlt/SimpleNote

This was the answer for years. I am 95% sure that I owe the link to Merlin Mann on MacBreak Weekly. It simplified capture by combining search and new note creation… still one of my favorite applications. I believe an nvAlt release note about [[wikilinks]] introduced me to the idea of a Zettelkasten.

4️⃣ VimWiki

Back when I was programming for a living VimWiki was an amazing option. Note-taking was always available in the same application as my work. I wrote a (now archived) article on it because I couldn't find the info I wanted online.

5️⃣ Homebrew Zettelkasten in Vim

I became frustrated by vimwiki taking over my markdown syntax in vim, and it had weird options… it's gotten a lot better since. Part of the problem for me is that I was attempting to do both a productivity system and a creativity system. Vimwiki and plaintext was absolutely capable… I just didn't have the discipline and practices required to keep from feeling overwhelmed. After I had used a Bullet Journal for a while… I was better prepared to understand and work productivity systems… and start to understand the value of a Creativity System.

6️⃣ Obsidian using ZK ID

I started toying with Obsidian… and while reading about paper zettelkasten I bought into a (faulty) usage of the permanent ID. I wrote a transformation script to take all my old sources of plaintext notes and make a flat markdown folder with unique IDs.

7️⃣ Obsidian using Titled Notes

After discovering I was wrong… I arrived at the simpler current version. It's been stable and slowly growing for six months. Less tinkering, more thinking and using. 🧠


I doubt anyone is going to read this… but self-documentation is interesting.

Some random takeaways as I consider my particular tooling journey:

  • Plaintext is king. Easily trackable, diff-able, portable.
  • Consistent formats makes transformation by script easier.
  • I should have tracked my notes in git years ago. Having a consistent backup I understand allows me to fearlessly experiment.
  • Notes are more just remembering facts. I never had a vision for tying together all the areas of my life… I guess I just kept my work/personal/family life compartmentalized before. Part of that productivity journey I guess.
  • Simpler is better.

I'm going to be talking more in the coming weeks about specific tweaks and customizations that I've made… hopefully they'll make more sense given this context, and I'll likely link back to this where it makes sense.

  1. Up until my first job, each project or context (being school!) had come pre-packaged with a place to put context: a workbook, study guides, etc. Suddenly I needed a place to put useful info, and no adult was going to remember it for me. In my first year of college, I used google docs to build a note wiki… and six months into school they banned laptops in the classroom. I was an unhappy computer science major… but my handwriting did improve drastically. 😜 

  • 2022-06-08 11:31:29 -0500
    Rename articles

  • 2021-10-06 11:30:26 -0500
    fix localhost link

    Thank you Bryan!

  • 2021-09-30 07:51:02 -0500
    Fix typo in title and permalink

  • 2021-09-30 07:49:56 -0500
    History of My Creative System