Conversational Journaling

Cameron Flint
5 min readNov 14, 2021
Image credit: Vidar Nordli-Mathisen on Unsplash

Last updated: Friday, Dec. 3 2021

Taking notes in the form of journaling is analogous to having a conversation with my own mind.

The realization struck me as, over time, my usage of Roam Research to document my daily thoughts, ideas, musings, research findings, and insights grew more frequent. I initially used Roam only as a wiki, but I gradually began to use it also as a “thought catcher” in order to collect my ideas on a timeline.

Snapshot from my daily notes timeline in Roam Research

Since I’m not usually at my computer when I do my best thinking, it’s useful to have a low-friction mobile capture method. While Roam Research itself lacks an app for on-the-go capture, there exists a third-party solution called phonetoroam. Any messages that I send to the p2r bot via iMessage or Telegram are automatically forwarded to Roam and appended to my “daily notes” timeline there.

Screenshot of iMessage on iPhone showing conversation thread with phone2roam bot
Using phonetoroam from iMessage

This method may seem archaic given that lots of note-taking applications have more sophisticated ways to capture notes than via SMS/MMS. But surprisingly, there is something natural about picking up the phone as if to “text my mind” in the same way that I send text messages to my friends.

Over a period of days and weeks a trail of mental breadcrumbs accumulates. These streams of thought, materialized onto a digital timeline, alternatingly diverge and converge as my mind wanders among the topics floating in my subconscious. The timeline acts as an anchor, providing continuity, and allowing me to pause and resume daydreaming sessions at will.

There is another application I use every day for work called Slack. Slack is a tool built for team communication, but I’ve discovered it to be a rich source of metaphor for how I organize my inner dialogue. (And as it turns out, I’m not the only one to think of using Slack as a personal notebook.)

Screenshot showing the Slack main window and the mouse pointer hovering over “Create a channel” in a right-click context menu.
Slack’s Channels, Threads, and Mentions are a useful mental model for journaling. (Image source: Slack.com)

Here is a quick rundown of Slack jargon in case the reader is not already familiar:

  • Conversations in Slack take place in channels that are each identified by a simple name: “#general,” “#engineering,” “#watercooler,” and the like. The channel provides a shared workspace for some subject, topic, project, workstream, or other context.
  • Messages sent within a channel often coalesce within threads, for instance, “Is corporate email down for anyone else?” could lead to a thread with multiple replies to the affirmative or negative. Threads are organic, short-lived, and focused.
  • Any message can contain one or more mentions, which in Slack are other people, team aliases, other channels, or links to other messages. Mentions can either be thought of as “pointers” to any other object in Slack, or more abstractly as a cross-cutting lattice of metadata perpendicular to the timeline.

As I continued to have daily “conversations” with myself on topics of personal interest using phone2roam and Roam Research, I realized that my journal entries could benefit from the same sort of organization that a sophisticated communication tool like Slack enables for its messages.

Too many notes mixed together from unrelated contexts clutter my single Roam Research timeline, just like trying to have company-wide conversations in a single Slack channel would be disastrous. In reality, my journal is several interleaved chronologies of thoughts across time, not just one.

(I can filter the timeline in Roam web/desktop, but the same doesn’t work well on mobile, so it can be annoying to wade through all the combined junk on my “thought trail” when I’m interested in following only one thread of thought back through history so that I can branch off of or continue it.)

The conversational metaphor has been transformational to how I think about interstitial journaling. It introduces ever-so-slight structure into how I capture fleeting thoughts, gently directing my fragile, ephemeral musings toward a handful of “thought lanes” like one would direct soap bubbles floating through the air.

Unfortunately phonetoroam does not have a way to associate different threads with e.g. different tags in Roam Research. If I am willing to move away from Roam for my conversational journaling, there are a number of replacement apps that might fit the bill. One promising option is Everlog.

Everlog is an attractive candidate for conversational journaling because of its clever implementation of journals and tags that allows a tag to be converted to a journal and vice-versa. But perhaps its most unique feature is its ability to create comment threads over any journal entry.

Everlog’s Journal, Tag, and Comment features map cleanly onto the Conversational Journaling model. (Image source: Apple App Store)

An implementation mapping in Everlog might look like this:

  • Channels ➡ journals.
  • Threads ➡ comments.
  • Mentions ➡ tags.

Importantly, entries across any or all combination of journals or tags can be viewed on a linear timeline using the search feature.

To be a little more concrete on the usage of “channels” (journals) vs. “mentions” (tags) in this model: I envision using journals for big buckets such as life areas, broad contexts, subjects, or long-running projects, while reserving tags for people, places, entities, and smaller topics. A tag might be “promoted” to a journal when it becomes a major interest, or a journal “demoted” to a tag when it becomes of lesser interest (such as when a project is finished).

Another app that could be capable of providing a straightforward implementation of conversational journaling is ZenJournal for iOS. I love that it supports “stream of thought” input similar to Slack, iMessage, etc., while permitting inline tags and filtering.

ZenJournal homepage

I’ve picked out Everlog and ZenJournal as examples, but I believe this kind of a system could be implemented in nearly any note-taking or journaling application — just to a greater or lesser extent of ease. I recommend against using document-oriented note-taking solutions, though, since it will be difficult to display filtered journal entries on a timeline that way.

Other software that come to mind (in the Apple ecosystem) are: DayOne, Upnote, Agenda, and NotePlan. All of these are date/timeline-friendly and support tagging for non-linear association. Notion or even my old friend Trello could work with some clever setup, I bet.

If you find yourself experimenting with this technique or have an implementation idea to share, I’d love to hear about it. Find me here on Medium, or on Twitter as @camflint, or drop me an email at feedbackforcameron {at} fastmail.com .

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Cameron Flint

Diving deep on topics related to note-taking, personal information management, and software engineering, with occasional diversions to less nerdy things.