Deep journaling done right

Among the greatest personal discoveries of the past year was journaling. No matter how tired or unfocused I am, I write at least a few paragraphs every single day now. It all started last spring as a simple provocative challenge: “Let’s agree to journal for 10 days.”. It quickly transformed into a habit that I feel is now hard to break.

I know how people often think of it. No one denies the benefits they have heard of in the media, but most people view it as an extra layer of complexity in their busy lives. I’d argue the opposite: the more you master contemplating your inner self with unstructured thoughts, the more you realize you’re moving toward a structured, minimalist life.

Grumbling about brainrot

First and foremost, I must get rid of any bias in our understanding of the concept of journaling. You might have heard of these apps: Day One, Apple Journal, Daylio, Journey, Stoic. They are all the exact opposite of what I am trying to promote in this article.

My idea of true journaling combines freedom, creativity, and immersiveness. It’s an active thinking process. All the above-mentioned “journaling” applications are digital products and someone’s business. What makes such a business successful? It’s user retention. They sell bells and whistles to hook casual users. While you seek happiness, self-reflection, and a vision for your life, they seek to lock you into their ecosystem or upsell services.

We can call these apps sophisticated diaries, but they have nothing in common with journaling. Let me unpack that:

• Apple Journal makes journaling a passive process by pulling photos, videos, locations, music you’ve listened to, and other data from the integrated apps. It gives you prompts — leading questions like “What’s something nice you can do for yourself today?”. It’s integrated with dozens of applications that just flood your feed with “suggestions” and “insights”. Streaks, stats, widgets, push notifications — a typical ADHD doom-scroller starter pack.
• Daylio turns journaling into picking your mood with emojis and describing your daily activities and feelings with colorful icons. This gamified strategy focuses on mood charting and pattern recognition — useful for specific clinical needs, perhaps, but the fact that it has 20 million downloads is telling. Again, there is a place for data logging, but most people don’t ever need it.
• Stoic introduces the same gamification and low-friction mechanisms, but in a cool black-and-white design. Any Stoic would laugh if they saw the name of their school associated with such an application. The app is full of streaks, push notifications, emoji mood trackers, “thought-provoking” prompts, and AI mentors.

So, if you want to collect all “what happened to me” memories full of media and “suggested” content to feel sweet nostalgia at some point in the future... Yes, please, use something like Apple Journal or Day One. If the idea of keeping a passive diary now strikes you as useless or even absurd, I’m with you. Passively archiving memories in a digital graveyard won’t strengthen your cognitive function or sharpen your memory. You’ll end up “disappointed” in journaling and never come back to this meaningless activity.

If not a diary, then what?

Reviewing all my notes, I recognize two distinct patterns. The first is a “regular” state that reflects my daily reality. It’s full of paragraphs answering what happened to me, how I felt at that moment, and why I felt like this. Sometimes the “why” question remains unanswered. If I knew all the “whys,” the entire exercise might feel pointless. So open questions are, in essence, a driver for deeper exploration — the ever-turning gears with “why” acting as the WD-40.

The second state is “flowing”. It comes rarely — maybe once a month. It’s easily recognizable: I review my notes, stop for a moment and scream: “Who did it!? Was it me who wrote this nonsense/masterpiece? Unbelievable.” I’m not bragging. On the contrary, it’s a very strange state. Mihaly Csikszentmihalyi spent his entire life searching for preconditions of the “flow”. I’m just grateful whenever it shows up. Those rare ‘aha!’ moments are the premium fuel powering those ever-turning gears.

It all started with a decision: “I’ll write whatever comes to mind and see how it goes.” The first notes were awkward. Fragmented sentences, promises to myself, and unanswered questions asked prematurely. That’s how every new activity begins — with awkward overconfidence. Mastering this activity is finding your own purpose. Letters on paper are just letters, but the act of putting those letters in a certain order is your attempt to find the truth in the world theater of the absurd.

But my life is like Groundhog Day...

It’s easy to write when something emotionally significant happens in your life. You fall in love, you meet a new friend, you feel lonely or excited. Or maybe you’ve just downed a double americano and entered ‘god mode,’ where thoughts stream through your mind as if all the cosmic microwave background is being pulled by gravity directly into your brain. Or maybe you read a book that influenced your life vision and philosophy.

There are empty days — days when nothing happens, when you’re exhausted, or when you just want to forget that day once and for all. These days turn into weeks, weeks into months, and now you’re seeking an escape from a work-sleep cycle. We’ve all been there. The greatest authors created their masterpieces in a state of deep despair, loneliness, and fatigue from life.

So yes — journaling makes sense regardless of the time of year or the weather. A quick, reluctant two-minute entry often evolves into an internal dialogue, an essay, or the accidental discovery of truth.

Put into practice

Keep it engaging. Digital vs analog journal

The handwritten journal is over-romanticized. It may be good advice for students trying to learn new concepts (as writing on paper reinforces memory activation), or people who benefit from sketches and creative chaos on their pages. I believe writing by hand is often the very thing that discourages people from sticking with journaling.

• Typing on a keyboard can be 10x faster than writing by hand. Your hands don’t get tired.
• You have access to LLMs, Google, translators, and other digital goods.
• You can search, edit, and erase texts.
• A random person cannot easily steal your journal and read your secrets.

Defenders of pen and paper who claim that digital writing has no soul: perhaps you should simply learn to type faster.

Keep it simple. Digital tools

Having already criticized mainstream ‘journaling’ apps, we can look at the two remaining categories: note-taking apps and generic workspaces. Here’s my own decision framework, which extends beyond mere journaling.

If you are a big fan of note-taking, or you’re building a “second brain” with lots of interconnected notes, choose Obsidian or Notion. Both are free but have totally different models. In short: Obsidian is for maximum privacy, top speed, and endless customization; Notion is for “everything just works out of the box.”

If you’re not much of a writer (yet), start with a single-page document in a note-taking app that’s already installed on your device, like Apple Notes. The only features you might need are headings, paragraphs, and bullet lists.

When I used Notion, I kept my main stream-of-consciousness journal in a single file per season (Summer 2025, etc.). With Obsidian, I just click the “Today’s daily note” button and it creates a new file for me, so now it’s one note per day. No practical difference detected, though.

Keep it frictionless. The flow of thought

I believe that the power of thought is primary, while the way to express it is just a matter of technique. Don’t box yourself in with rigid mental boundaries. Write as if no one will ever read it — a true soliloquy. For example, forcing yourself to do it in a specific language undermines the entire purpose of free thought. Often, it just “feels” like certain thoughts are ideally expressed in a certain language.

Another way to reduce friction is to aim for a near-meditative state. Stay all by yourself or convince yourself that you’re alone. Put away the phone, grab a caffeinated drink, turn on drum ’n’ bass or a hang drum in your headphones — do whatever you can to prevent thoughts from leaking beyond your imaginary 1x1 boundaries. Essentially, it’s one of the preconditions of entering the flow state which requires the least preparation.

Lastly, write when you feel like writing. Maybe your next brilliant idea will pop up while you’re taking a shower; now you’ll finally catch it before it evaporates. Starting with a random thought is also an effective solution for a “blank page” paralysis.

Journaling vs talking to LLM

Do you use an LLM as a personal psychologist? I bet you do. Honestly, I talk to LLMs a lot. Twenty conversations per day or so. I configured it to be excessively skeptical and to never blindly agree with me. This helps me break it out of its default ‘echo chamber’ mode. I found that mirroring thoughts is potentially harmful to critical thinking skills. But even the ever-skeptical mode has the same pitfall. Each response from an LLM that confirms or doubts your question causes a dopamine spike and naturally reduces your ability to find and extract information with your brain.

I find LLMs extremely harmful for deep thinking sessions and journaling. Your subjective interpretation of reality must come from the inside. Asking an LLM to criticize, analyze, or refute an idea turns off the brain immediately, and often brings you back from the exalted state of the creator. The solution? First, offload everything that’s on your mind. Only when you’ve exhausted your internal thoughts is it ‘safe’ to engage with the external world.

Not a magic pill. Caveats

If you start journaling in the hope that it will improve your speaking social skills, you’ll be disappointed; that’s a misconception. Practicing thinking and writing makes you a better thinker and writer, nothing more. I’ve consistently journaled in English, yet it has contributed almost nothing to my speaking fluency. Writing is asynchronous synthesis, while speaking is synchronous retrieval.

Another caveat is quantifying — worrying that today you wrote two sentences, while yesterday you composed two paragraphs; worrying about a skipped day because you were too busy to reflect; treating your journal as something that demands maintenance, and writing for the sake of writing to reduce this anxiety.

So, journaling for the sake of..?

Typically, humans don’t observe their thoughts outside of meditation sessions. Seeing your thoughts materialized “on the page” is a form of metacognition. It’s the first step on a road to mindfulness which reveals moments when you become aware of your awareness.

For me, self-reflection, cognitive training, and the feeling of being alive became the main drivers that send me running to my desk to open my notes app. Your drivers may be different, perhaps more down-to-earth and practical, or simply offloading your worries to make it easier to fall asleep.

Now that you’re equipped with a foundational understanding of deep journaling, it’s time to integrate it into your busy life. Commit to 10 days. Experiment with formats — not to see if you “enjoy” it, but to gauge how much noise it can clear out of your life.