Reflections on 4 years of Writing with Obsidian

A personal reflection on 4 years of using Obsidian for note-taking, exploring how it shaped my writing habits and knowledge management through major life transitions from 2020 to 2024

  ·   13 min read

It’s been 4 years since I started using obsidian to manage my notes and my work.

I couldn’t trace back the exact date when I started using obsidian, but the earliest record I could find were a few DMs and screenshots from December 2020, messages I had sent to some of my friends saying hey I found cool thing for my notes and have been setting it up for a few days.

I had discovered Obsidian and Roam Research around the same time and that led me down a few rabbit holes to discover the cult of PKM, zettelkasten etc.

I ended up reading the How to take Smart Notes book and following the LYT youtube channel to get started.

Obsidian has been the most sticky note-taking tool I use, four years is a lot for this category of software. My life completely changed from 2020 to 2024. Got an internship, which led to a full-time remote job, moved cities, started a living on my own, started traveling solo, changed my mind about a lot of things. You know, the roaring twenties.

And I’m happy to see how my obsidian vault has evolved in this era of massive flux in my life.

I wanted to talk about my current vault setup and also to write down my reflections about using obsidian to become someone who writes things down, a lot.

In the past few years, obsidian has become the first thing I open when I start my day.

Current Setup and Evolution #

My current vault sits at 776 notes, 22k lines in total. The median note size is 24 lines. In pure numeric terms, it would be a mediocre ~800 page book.

You can view the current graph view of my vault in this thread which I keep updating every few months.

My productivity setup as of today is just two tools – Obsidian and Akiflow. I use Akiflow to manage my tasks and my calendar, everything else goes via Obsidian.

I use the default theme and a few plugins to make life easier. I used to rice my obsidian a lot, but my current intent is to keep things as simple as possible so I can focus on the writing a lot more.

I want it to open and run as fast as possible, thus I don’t do heavier themes or anything that would slow things down. And the default theme is pretty slick, so no complaints there.

My hotkeys mimic the keybinds from my code editor – for quick switch, command palette and splitting editors.

I use the following community plugins

  • Periodic Notes for periodic journalling with templates
  • Dataview for creating dynamic indexes on my notes
  • Calendar for quickly opening daily notes
  • Home Tab for quick access to my most used notes
  • Tag Wrangler for searching via tags and building a hierarchy of tags

I also use Obsidian Sync, mostly for a nice mobile experience. Also I want to pay them some money. I really want Obsidian to stick around, love their approach with being 100% user-supported.

The way my vault has evolved is by moving to simpler and simpler structures to organise my notes.

When I started out, I would nest notes in topical folders. Very simple.

This was easy to manage in college as most of my note-taking was around university courses and umbrella technical topics. But with time there came notes that would ideally fit in multiple folders, and that become a point of friction.

So I ditched the folder hierarchy and moved to using tags for organising notes. All notes go in the same folder. I attach multiple tags based on the topics that note folds under.

This approach made the setup much more flexible, allowing me to build a many to many association between notes and tags. Very representative of how our thoughts work.

Tag wrangler is a very good plugin to achieve this, you can also create nested tags and that allows you to build a hierarchy of tags. My tag hierarchy is mostly flat, I try not to create a very elaborate hierarchy of tags because then it would become the same problem as the folders. But building one level of nesting in tags to create some structure comes in handy.

Like every other note taking snob, I try to keep my notes as atomic as possible and backlink them to similar ideas. But I don’t take this atomicity and backlinking extremely seriously, the important thing is to get the idea down, explain it in your words and then work with the note over time. Trying to get everything perfectly atomic and backlinked in pristine manner right from the get go is just too much friction.

I have three journaling routines – day, month and year. For planning, I just do daily and quarterly. I have a template for all of them.

I start my day by opening the day’s note, mostly using the calendar plugin.

The first thing I do is just write everything that is going on in my head from the previous day/night, I try to do this exercise for 15 min. This is my minimal version of morning pages.

After this, I start my work day – inbox zero on slack, jira, notion etc. This daily note is open and pinned throughout the day, this is my destination if I have to quickly note down something or store an interesting link for later or make a quick throwaway list.

I use dataview to create dynamic indexes on a my popular tags (projects, blog drafts, contacts etc.), these become my map of content pages.

I also use my paper notebook to scribble and draw things – diagrams, mindmaps etc, those are much easier to get out on a piece of paper.

Usually at the end of my day I branch out and create other notes if needed based on the dump that accumulates in the daily note.

On weekends, I spend some time cleaning up and revisiting notes added over the week. I have a tag called #tbw (to be written) that I use to keep track of notes that I want to write but currently are just a bunch of scribbles. I track it using a dataview index. The weekend writing routine is just draining the #tbw index.

Doing this routine consistently over the years has helped me write a lot more. All of this “writing to figure things out” came with a bunch of learnings and reflections, I’ll try to share some of them in this post.

Cult of Done Manifesto #

The written word is weak. Many people prefer life to it. Life gets your blood going, & it smells good. Writing is mere writing, literature is mere.

– Excerpt from “The Writing Life” by Annie Dillard

When I started on this journey, the intent was to grow into someone who writes a lot, because I had realised in fragments that writing clears up your thinking a lot. Your stupid arguments become a lot more obviously stupid when you write them down. Paul Graham has some sweet essays on this very topic 1 2 3

But somewhere in the hunt for building the perfect setup to write more, I got lost. I kept chasing this non-existent utopia of note management systems. I had not made any progress on my actual muscle of writing, I just kept swinging between a bunch of tools like evernote, dropbox paper and notion.

So the intent with setting up obsidian was to stay away from all that fluff, keep things so simple that getting to the point where you can just write would be brain dead easy.

Sticking to this mindset was what actually got the ball rolling and got me writing everyday.

And this is my first reflection in this whole journey – it’s very easy to keep pretending and trying out new tools in this space and enjoy the dopamine hit of looking at your shiny new setup.

There is no perfect setup, the only metric that matters is: are you writing or not ? Execution is everything.

Write to get things done. Write to understand yourself and your decisions better.

The Cult of Done Manifesto greatly shaped how I structure my writing system and my vault. It articulates something I struggle a lot with – closing things and moving on.

  1. Accept that everything is a draft. It helps to get it done.

Everything is a draft, everything is always evolving and is a work in progress, there is no virtue in chasing perfection all the time. The more you iterate, the better you get, so focus on iterating more.

I also noticed it’s easy to fall into the trap of just writing about things and not really translating that into action. I really did not want to become that person.

I keep avoiding rabbit holes where I’m just writing about some idea rather than building or executing on it. Action first, always.

My relationship to my writing is deeply personal. I mostly don’t write to publish, and approaching it that way helped me find my voice a lot more easily.

I write to become a better engineer and a more complete person. I understand a lot of hard technical topics by writing about them. I process and manage a lot of my complex emotions by writing about them. And I am excited to see how this relationship evolves in the coming years.

Self Awareness and Private Investigation #

Man hands on misery to man.

It deepens like a coastal shelf.

This be the Verse by Philip Larkin.

I met a very philosophical designer in my hostel on my solo trip to Munnar in March, 2023.

We spoke all night till it was dawn. It’s still one of my favourite conversations I have had with a stranger.

We talked about love, films, music, creativity, finding yourself in your 20s, work etc. You get the vibe. He had quit his job as a designer and was going all in to produce his first album.

We talked a lot about this idea of private investigation of your own life, and how you can use it to become increasingly self aware. It’s one of the big things that has stayed with me from that conversation.

As a person, you are handed a lot of things and ideas that you’re supposed to believe in. You parents and family programmed you a certain way, you school did too, so did your early set of friends. They taught you what “normal” means. By the time you’re 18, you carry a lot of things inside that are just ideas handed off to you.

Your parents tell you your relationship with god, they tell you how you’re supposed to make and manage money, your early friends set expectations on what a “good” friend means. By the time you start making money, you probably have a vision for your life that is very much influenced by your upbringing, or worse, influenced by instagram.

That vision could be something you agree with or it could run you hollow by the time you hit your mid 30s.

But, you do get chances to revisit a lot of those ideas in a spirit of exercising high agency. This mostly happens when you move out or start travelling solo. One of the reasons I am a big advocate of not living with your parents.

You might not agree on some of the things your upbringing gave you, and I think it’s crucial to go through that exercise regularly in your life to find and curate the lifestyle that makes sense to you and makes you happy.

So apart from my regular note-taking, I also use obsidian to do this sort of private investigation / reflective writing on different aspects of my own life. It helps me become more self aware, it helps me find my blind spots and biases.

When we write, we’re forced to make explicit what is often implicit in our minds.

It has helped me make decisions that just make sense to me. This also trickles down to me figuring out my work as well, it helps me identify my superpowers and pick and drive projects where I can create the most impact.

Writing is such a hack to become dangerously self-aware and maintain that over time.

In this era of LLM overload, this is a great way to constantly access and be in touch with your humanity.

Catalog of Human Experience #

I understand the need to be awkwardly genuine online. I understand the need to get over your cringe and keep writing online to increase surface area for serendipity. But most people want some pieces of them to be only for people they know closely. I am one of them.

I want to document my deeply personal experiences in my private capacity and own that full catalog. If my entire human experience can just fit in a zip file of a few terabytes on a hard drive that I own and only people I pick get access to, that’d be awesome.

A lifetime is around 70 years. If Bryan succeeds, it’d be around 200 years.

Giving up all of this data that we create about our life, and handing it over to platforms like X and Instagram is not durable. Companies and platforms are transient, they may or may not last our lifetimes.

This is where obsidian’s core philosophy of file over app brings a lot of relief, because it’s easier to own files, it’s easier to share files.

When you pass away, your entire vault filled with notes that tell the the story of your life can just be exported to a book and given to your friends and family.

Millennials and GenZ are the first generation that have a chance to leave an entire catalog of their lives for their loved ones. But most of us just poast for clout and brand deals and I am really not interested in curating my deep personal experiences like that.

I just want it to be simple, personal and durable. And obsidian has given me some hope of actually achieving that goal in some capacity.

I hope these markdown files, which contain so much of myself, will last my lifetime. I want to share pieces of my writing both publicly and privately. I want to share them with my family and close friends when the time feels right. Through these writings, I just want to express what life felt like to me.

Looking Forward #

It has been a fulfilling journey so far trying to build a system that helps me write more, and I’m really grateful for this glorified markdown editor that enabled me to grow like this.

I am very much looking forward to dictating a lot of my notes.

I’ve been using this app called VoicePal, which is a copywriter in your phone. You can dictate your ideas, it transcribes and edits them using AI, asks a bunch of follow up questions to complete the piece, and then you can export it to a preset style – blog, letter, tweet, linkedin etc.

I used it a lot recently to write some documentation for a tool at work and this flow is very fluid and fun.

I’ve pre-ordered Pocket as well. The team says the software is going to be open-source, I’d probably figure out a way to sync transcriptions to my obsidian vault.

I worked on some parts of this blog post while walking around and dictating late at night after dinner. I look forward to tools that enable me to do that more.

I’ll hopefully write another set of these reflections about writing with obsidian after a few years, when I feel like there are enough interesting reflections to put together.

I hope this story of mine would add to you getting started on your journey of writing to understand yourself better, if you have one already, please dm or email me, would love to read.


Notes