Going Beyond Todo Lists While Journaling
Why should I journal? I still ask myself this every once in a while. We often think of journaling as a simple act of recording daily events or maintaining todo lists. For many people this is a habit that even starts in childhood. I only really got into it once my career began. It's become a necessity to me. A powerful exercise for organizing thoughts, gaining clarity, and making sure all my previous energy carries through to my future self.
The System Trap
It's so easy to get excited about a new journaling system. You discover Obsidian's linking features, or Notion's elegant databases, or perhaps the tactile appeal of a fresh Moleskine notebook. Some even dive deep into tools like Neurite to explore the fractal nature of thought itself. Suddenly, you're spending hours setting up the perfect system, crafting templates, and designing workflows. I've been there—the sensation of starting with a fresh slate is akin to finally cleaning that long-neglected room. It's all fresh and full of possibilities.
But here's what I've learned: the system matters far less than the actual practice of writing. The perfect organization structure won't magically make you more reflective or insightful. Sometimes it even makes it harder to write or stops you from getting true value from the routine.
Breaking Free from Performance Journaling
Early in my career, my "journaling" consisted mainly of standup updates and ticket comments - carefully crafted messages meant for others. While valuable for communication, these weren't personal reflections that I would ever engage with again. They were performances, shaped by what I thought others needed to hear to help them do their jobs.
Once I started writing purely for myself I finally started to "get it." No audience, no formatting requirements, no need to sound professional or polished. Just raw, honest thoughts about what I was experiencing, learning, and questioning with as much detail as I felt needed to revisit or evolve from a given moment at a later time.
Preventing the Routine From Killing the Value
One of the biggest challenges with journaling is maintaining its value over time. When it becomes routine - "Today I did X, tomorrow I'll do Y" - I believe it loses much of its power as a tool for insight and growth. This is why I built triday, a tool that introduces elements of randomness and guided prompts into the journaling process.
While triday helps, it's still not quite enough for the long run. I believe LLMs may have a role to play here - acting as a sounding board to sanity check our thoughts and ensure we're capturing them in a way that remains meaningful both now and when we need to recall these experiences later. Voice in particular could be an exciting evolution of journaling where it can start to call out whether or not you really mean something based on the nuances of your voice.
Making It Work for You
- Write for yourself, not for an audience
- Start simple - use the first tool you think of when you need a blank page
- Don't worry about perfect grammar or structure
- Consider whether you care more about capturing insights or events
- Review periodically to make sure you're still getting value
The Real Value
The true power of journaling isn't in capturing every detail of your day or maintaining a perfect system. It's in the moments of clarity that come from putting your thoughts into words, the patterns to your thought structures that you notice over time, and the deeper understanding you develop about yourself and your work. I'd be embarrassed to say I'm the same person I was a few months ago. Journaling is a way to make sure I'm continuously improving. This to me is really what I appreciate productivity as at the moment. It's all about doing better and not necessarily more.
Whether you're working through a complex problem, processing emotions, or planning your next big project, the simple act of writing can help bring insights from the chaos, the mundane, and/or the overlooked. But perhaps most importantly, it creates a dialogue with your past, present, and future self - a reminder that progress isn't just about moving forward, but about understanding where you've been and why you made the choices you did on your journey.