This is post #2 of my 100-post challenge. This one is for friends interested in writing practices and musings on how they might relate to publishing online and doing regular reflections.

Portland, OR

Over the past half-decade I’ve had an evolving and contentious relationship with writing, note-taking, newsletters, and publishing. It’s spanned a range of apps and workflows (Apple Notes, Evernote, OneNote, Notion, Roam Research, Obsidian) and cycled through a range of habit trackers, goals, and check-in systems; all of which have come and gone.

For the past three months I’ve been consistent with a daily writing & weekly review process, and I think this might be the approach that sticks.

Part of the inspiration came from seeing my friend Dave diligently writing every single morning – rain or shine – showing me a) it is possible to fit into a busy, unpredictable schedule and b) consistency begets magic.

My increasingly chaotic travel schedule was also met with a rising desire for a grounding habit; one I could partake in regardless of where I was or who I was surrounded by. Reading through War of Art also gave me some new lenses with which to look at my habits through.

untangling writing and publishing #

Looking back over the past few years of failed writing practices, I now see some common factors that reliably killed my desire to write and share that writing:

  1. putting too much structure in place in the form of morning questions, evening reflection scores, and weekly review templates which imposed frames on what should’ve been pure stream of consciousness output.
  2. shackling this personal review to a public newsletter in the form of a weekly post-review newsletter. This meant for me to write my newsletter I had to finish my review. No review, no newsletter, and lots of guilt.
  3. announcing every blog post over email, Twitter, and Instagram resulting in occasional timely & relevant social feedback but costing valuable time thereby reducing my desire to go through this process even further.
  4. relying too much on collecting feedback, which involves waiting for that feedback to arrive; sometimes in mulitple cycles. This makes sense for important essays or sensitive topics but my goal is to get writing out; the feedback can come find me if it cares to.

I’ve since gone back to the drawing board on this process and have something that feels healthier and more sustainable.

morning writing ritual #

Wake up, preferably without an alarm. Depending on where I am, walk to buy a coffee – ideally passing by a variety of trees on my way there. If I’m in a city, I make my bed and brew some coffee or walk to a nearby coffee shop.

I open up Obsidian, full-screen it, type [[morning ritual]], and get at it: I just let it all out. Where am I writing this from? How am I feeling? How did I sleep? What happened yesterday? Any simmering reflections? Nagging things that need to be taken care of? What am I worried about? Excited for?

Once my emotional brain realizes it’s been given space to exist and be listened to without judgment, the stream slows down. My writing becomes quieter; finer; more thoughtful. Ideas I’ve been stewing over to try and experiment with. Reflections that need to be sussed out and untangled; a process that might take several days or weeks to fully unravel but relies on time and space for this to complete.

During this process I don’t worry much about adding backlinks, formatting, or making it make sense. That will come later; for now I’m channeling what wants to be written. As soon as I reach an edge of one thought, I put down a - and start the next one. It’s the equivalent of “end note” and lets me get out all my thoughts as independent notes, still contained in one daily file 1.

[[morning ritual]]

some thoughts


another thought


yet another thought

weekly review process #

rephrase: Given the last times I imposed semi-rigorous structure on processes which are suffocated by that very structure, my approach weekly reviews now has three core principles:

  1. let the structure emerge over time. I made my first reviews by opening a new file and simply writing about the emotions that came up in the process of reading my week’s worth of notes. Over time, I started noting down things that went well versus ones that didn’t. Eventually, reflections and a week-ahead plan emerged. But I don’t hold myself to filling out every field; I hold myself to showing up.
  2. schedule it on Monday mornings, in contrast to trying to do it on Friday night and over the weekend. It’s the best time I’ve found because it’s at the beginning of the week, and everyone else is too busy commuting and responding to emails to bother me. Now that I have more control over my schedule, this feels the most appropriate use of my Monday mornings.
  3. withhold judgment & productivity framing This isn’t a time to criticize my past self and missed objectives; it’s a time to listen and learn about how my future self wants to be treated. I try to avoid looking at it as a publishing or productivity system and instead frame it as a wisdom practice; a space to be treated with both respect and playfulness.

My current template is as follows, but it’s subject to change and simply a snapshot of the current point in time.

## meta

## writings in progress

## week takeaways and review

## what went well?

## what didn't go well?

## week ahead intentions

## photos/screenshot review

## apple notes review

concluding thoughts #

I admit it: I still have plenty of reservations about my tooling, publishing layer, and note-taking system. But if people were able to share their thoughts with the world using typewriters, candlelight and publishing houses, I can share mine with billions of transistors at my disposal and a global network connected at the speed of light. It’s just a matter of getting my thoughts out of my head regularly, and sharing those that seem to come up over and over again.

  1. roam vs obsidian; bullets vs files; hierarchy vs stream. A lot to unpack here, for another post. ↩︎