From Doubt to Habit: My Journey from Skeptic to Frequent 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 has now 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, 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.
Just Start Writing
Simply starting to journal any time and anywhere is the biggest step you can take towards being more reflective and insightful. You don't need that fancy leather-bound notebook or that expensive software. The notes app that came with your phone or a basic text editor on your computer is more than enough to begin your journey.
Once you understand what you actually need from your journaling practice, then you can invest in more sophisticated tools. Focus first on the habit of reflection itself.
Breaking Free from Performance Journaling
Early in my career, my "journaling" consisted mainly of standup updates and ticket comments. All of these were 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 that moment.
Preventing the Routine From Killing the Value
One of the biggest challenges with journaling is maintaining its value over time. When it becomes just another routine task or fill in the blank template ("Today I did X, tomorrow I'll do Y"), it loses much of its power as a tool for insight and growth. Having different modes of expression can help keep the practice fresh and meaningful.
Exploring Journaling Methods
Different goals call for different approaches. Experimenting with various journaling styles can help you discover what resonates most with your current needs. Through building various tools within reset (a collection of mini browser apps that give you a moment of recalibration), I've created several free, private, and quick ways to explore different styles of journaling:
- stream: A judgment-free space for stream of consciousness writing. No grammar rules, no structure. Just pure, unfiltered thoughts flowing onto the page. Excellent for overcoming writer's block or simply clearing your head.
- future: Write letters to your future self, with scheduled delivery dates. A powerful method for setting intentions, tracking long-term goals, and maintaining a dialogue with the person you're becoming.
- shadow: A beginner-friendly approach to shadow work journaling, helping you explore and integrate different, perhaps less acknowledged, aspects of yourself through guided prompts.
- release: Sometimes you just need to let go. Write your thought, and with one cathartic button press, watch it disappear. A digital version of the therapeutic practice of writing and burning, useful for more fully processing your thoughts.
- remembrance: A gentle introduction to grief journaling, offering a guided space to process and honor memories and emotions in a supportive way.
These tools offer simple ways to try different journaling practices without commitment. Start with what resonates. The key is finding what works for you through experimentation, and these lightweight experiences can help you discover which practices you might want to develop more formally later, perhaps in a dedicated app like Obsidian or a physical notebook.
Making It Work for You
Here are some tips for making sure that journaling stays a habit that's valuable for you:
- Write for yourself, not for an audience
- Start simple, just use the first tool you think of when you need a blank page
- Don't worry about perfect grammar or structure
- Review periodically to make sure you're still getting value
- Experiment with different approaches as you discover your needs
- Don't feel pressured to write every day, this defeats the purpose of genuine journaling practice
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 passions. 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.
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 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.