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.

But 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 almost 4 years now.​​

What is Daily Questions Journaling?

Daily Questions are a form of prompt-based journaling that focus 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 Obsidian University Starter Vault.

Bonus Nerdery: I’ve actually streamlined the entry of the values in my Daily Questions journaling recently using a Shortcut I describe in this YouTube video. Both the iOS and macOS versions of the Shortcut are also included in the Obsidian University Starter Vault linked to above.

Something Cool: Force Note View Mode plugin

A plugin I stumbled on recently that helped make my journaling workflow a little bit better is the Force Note View Mode plugin. This allows you to force Obsidian into a specific view mode whenever you open a note in a specific location.

Since I use my Daily Note for other things (like daily Bible reading and habit tracking) using the Obsidian Tasks plugin, I’ve found that being in Preview Mode ensures that the repeating tasks get logged correctly. So I use this plugin to force Obsidian into Preview Mode every time I open a Daily Note.

Book Notes: Triggers by Marshall Goldsmith

In addition to the Daily Questions I talked about above, Triggers by Marshall Goldsmith is a great book about behavior change. It’s a great complement to Atomic Habits by James Clear and helped me understand the role of our environment in habit formation a lot better.

If you want to download my notes, click here.

— Mike