I’ve been journaling for about 15 years. And truth be told, for many of those years, I’ve been struggling to make the journaling habit really stick.
But a few years ago, I came across a technique that made journaling easy for me by eliminating the guilt from traditional prompt-based journaling called Daily Questions.
In this newsletter, I’m going to share why I find it so effective and my personal workflow for journaling in Obsidian.
Let's start, though, by talking about where things went wrong for me.
The Problem with Prompt-Based Journaling
To be clear, I believe that journaling prompts can be very powerful. When you learn to ask the right questions, the answers usually become clear.
However, I found that I was struggling with prompt-based journaling because my prompts ended up focusing on what I accomplished:
- What did I learn today?
- What did I create today?
- What did I do for exercise?
The problem manifested whenever I had a bad day as I found myself resisting my prompts. If I had a crazy day at work and didn’t get a chance to read today, I would feel personal shame in having nothing to say for my “what did I learn?” prompt.
Obviously, this pressure is entirely self-made. But it didn’t matter — after a while, I found myself resisting journaling.
Every day, I’d get nervous whenever I sat down to journal. I’d frantically rack my brain for something positive or noteworthy that I could use when answering my journaling prompts.
So, eventually, I stopped. I’d skip one day, then another later on, then two in a row, and before long I'd have weeks in Day One without an entry.
But I knew that journaling was important, so I’d recommit and resolve to try again. I’d pick different prompts, set up a new system, and try again.
And the cycle would repeat every 3 to 6 months. That is, until I came across the concept of Daily Questions in the book Triggers by Marshall Goldsmith.
Using Daily Questions, the resistance is gone. And I've been journaling every day for over 5 years now.
What is Daily Questions Journaling?
Daily Questions are a form of prompt-based journaling that focuses on the intention, not the results.
Instead of asking yourself “what did I accomplish?” you ask “did I do my best to?” and rate your effort on a scale of 1 to 10.
The numbers are completely arbitrary and represent the effort, not the outcome.
For example, one of my daily questions now is, “Did I do my best to exercise?” The score I give myself will be reflective of my effort, not what I actually did. So if I’m training for a half-marathon and I cut short a training run where I was supposed to go for 10 miles but I only did 6, I might rate that a 7. But if I’m getting over a cold and force myself to just get out there and do a slow 3 miles, I’d likely rate that a 10.
The belief is that if I consistently put forth the effort, the results will take care of themselves.
And that’s exactly what I’ve seen.
My Obsidian-Based Journaling Workflow
In the book, Marshall explains how he tracks his daily questions in an Excel spreadsheet. That alone almost turned me off to the idea, but after I understood the process, I started thinking about other ways I could implement this.
I tried many different apps, but it wasn’t until I started using Obsidian that it really clicked.
Here’s how I set it up:
First, I use the Daily Notes core plugin as the base. This creates a new daily note in my Daily Notes folder where I answer my daily questions, and I use the standard date formatting of YYYY-MM-DD.
Next, I add my Daily Questions to the Daily Note template. Each question is followed by a tag (i.e. #dailyquestions/learn) and a colon. This allows me to assign a value to each tag that is anchored to the day of the Daily Note when it was created.
But the really cool part of this is using a plugin called Tracker, where I have a code that shows me the scores for each tag plotted on a line graph:
This allows me to see overall trends by zooming out.
I review these at least every 3 months as part of my personal retreat process (I did a YouTube video on this here). If I see something that I need to address, I can dig deeper and figure out the root cause and what changes I might want to make.
The codes are pretty technical, but I do walk through how they work in this YouTube video. And if you want to download them and play with yourself, I provide the template files in my free Practical PKM Starter Vault.
