Discover more from Cultivate
A brief history of my note-taking habit.
Hey friends - quick message to say that I am building a course! If the following article interests you, then you might be interested in Everyday Obsisian. You can sign up for more details, and everyone who signs up between now and release will be in with a chance of free access to the course when it releases!
— James ✌️
Writing has always been something that I have enjoyed. At school I took great pride in my handwriting, the act of simply putting pen to paper and then writing a few lines both therapeutic and satisfying. This dwindled in sixth form (high school for any American readers), my neat and thoughtful writing style was bullied out of the way for speed optimisation. Turns out they don't grade essays on handwriting style.
When I left school at 17, perhaps a decade passed before I ever really wrote anything more than a few lines again.
The turning point was when I was learning to code. Most of my early lessons were written down in a notebook by hand, even handwriting small programs. That same therapeutic feeling I got as a child came flooding back to me. In hindsight, this was far from optimal, but I also wonder whether I would have stuck with my studies has I not had the satisfaction of putting pen to paper and seeing the visual evidence of the knowledge I was consuming.
Writing in a notebook was something that followed me around for the first few years of being a software engineer. I would turn up to meetings and present ideas and UI changes from my book of notes rather than a digital tool. My colleagues humoured me, which was much appreciated and many commented on how clear and articulate my thoughts were presented.
It just felt more natural to me that when I had an idea, the best way I could articulate it would be to draw it down. Pen and paper is frictionless, it's a fairly common occurrence for me to grab a notebook and draw a mind-map or a list when I want to explore an idea. I have never been able to truly replicate that with a digital tool (and still don't to this day).
I have captured many of my lifes biggest turning points with a pen and paper. The highs and lows of family and professional life, the thought process behind key decisions throughout my life as well as the small things like what I was appreciating at the time are all catalogued in my collection of journals. You never come away from writing thoughts down feeling worse off, that is the beauty of it.
When I started as a manager my method of working out of a notebook started to creak at the seams. Primarily I was struggling to find pieces of information that I had written down before. This was the point I started looking for digital tools.
James enters the 21st century.
As a people manager there is a lot to keep track of - meeting notes, 121 notes, performance reviews, brag docs, technical docs - and that is even before keeping notes for yourself.
I break my notes down into four main categories, and these stay pretty true to the type of notes I was capturing in my notebook:
Personal: thoughts/feelings and general ideas. I also bundle notes I keep with my wife in this category and this could be anything from financial notes to sentimental writing (my wedding speech & vows etc).
Work: this is everything I need for work to be effective. Whether that is keeping track of meetings, writing documentation or notes between myself and a report.
Input: these are notes that I take from media I consume - books, articles, films, courses etc. Many people try to capture everything but I try and keep my input notes fairly articulate and intentional.
Output: this is any of my written content for my newsletter or social media.
I have tried numerous apps and digital tools for note-taking, and I am the first to admit that none are perfect. People have a tendency to try and plug the imperfections with other tools until you are left with this massive behemoth of complexity and SaaS subscriptions - that is not me.. I am ALL about the simplicity. (I actually like Apple Notes, but find it virtually unusable due to a couple of things).
The first digital tool I invested time into was Notion, which is a powerful team collaboration tool slash wiki which many people use for personal notes. I am a fan of Notion for teams, but as a personal tool it didn't fit the bill for me.
You can do a lot of neat shit, but the tinkerer in me spent more time playing with the tool over using it for the practice I was there for in the first place. Keeping notes.
When you have a pen and paper, there is not much you can do other than write. With Notion, there is a whole host of different techniques and features at your disposal, and this just was too complex for my needs and too dangerous for the builder in me. I have said before, for personal notes Notion is like reaching for a sledgehammer to tap in a drawing pin. Not to mention, it is at times painfully slow and requires an internet connection to use.
Up next came Roam Research, and this was my first entry into what is known as the PKM (Personal Knowledge Management) world and the group of enthusiasts that it holds. As the name suggests, Roam is a research tool. A simple user interface akin to a command line, the selling point of the tool being that you can build connections (backlinks) between notes and build a knowledge graph of connected ideas.
I quickly became a believe in the benefits of note taking in this way (and still am, but less a believer of Roam the tool) and I used Roam for a good amount of time.
One of the selling points of Roam is that there is very little formal structure, as the intention is that structure will organically build itself over time when you make connections between notes.
In a sense, Roam is possibly the most similar of the digital tools to a notebook. You are greeted each day with a blank page in which you can write. Ironically I ended up giving up on Roam for similar reasons that I felt my physical notebooks were less than optimal.
Folders don't exist in the Roam world, but this was something I found I needed. I would lose notes and not be able to find them again easily. Personal notes about life and my family would not sit neatly alongside professional notes. Over time it became a mess and there was very little I could do to combat that - much like the notebooks sitting on my shelf.
Thirdly, was Obsidian.
Obsidian shares some similarities with Roam Research that I find valuable, in particular the back-linking capability and the knowledge graph. Where it differs however is that it is built to work with markdown files on your machine, whereas at the time Roam was entirely cloud based.
At first I didn't like Obsidian. Because folders exist, you almost need an idea of a architecture before starting but I didn't know how best to find that structure. The beauty of Obsidian is it lets people build their system in the best way to suit them, with various methods of navigation and organisation (Links, Tags, Folders etc) but the downside to all that freedom is it is hard to know where to start.
I turned to the internet and found very little inspiration. There are tonnes of tutorials out there of people building systems in Obsidian, but everything was too niche or too complex for my use case. I bought in to the Zettelkasten methodology (which I discovered through one of my favourite authors Robert Greene), and many people were cultivating digital Zettelkastens in Obsidian and this seemed to be the most popular tactic to teach. I strongly believe if you are an author or researcher, then this technique is extremely effective, but I am too smooth brained to be either of those things really. I just wanted a way of keeping track of notes.
I persisted with Obsidian, won over by the flexibility and customisability the tool presented. It felt familiar in some way, almost like VSCode but for writing, and I liked that I could make it feel my own with themes, plugins and hotkeys. Also, I was convinced at this stage I was the problem more than Obsidian and over time I created a system that worked for me that prioritised simplicity and discoverability above all else.
I do still think there is a lack of approachable content the average person can use to make Obsidian work for them. The content for Notion is generally fairly approachable and I think having templates that people can piece together and not have to start from scratch is a big leg up over Obsidian. This lack of content is why I am creating my own course Everyday Obsidian (more soon).
It's been about two years now, and we are still in a good place. I have kept an eye on some of the other developments in the space (Reflect, Tana etc) but shiny object syndrome is a real thing. The amount of people I see that switch apps frequently due to a new 'super app' arrival only to double back a few weeks/months later is frightening.
There will always be something fairly romantic about pen and paper for me, the slower pace somehow stirs the creative juices just that little bit more I find. Pouring my heart onto a screen doesn't provide the same catharsis that a book rewards me with. Despite how smart digital tools get and how effective my system for keeping notes becomes, I will always make time to put pen to paper.
However, I genuinely believe that Obsidian has transformed the way that I work and it deserves a lot of credit. It has made me more focused, more intentional, more productive and more balanced.
Is it right for everyone? Probably not. But I do think that if you are struggling with the things I mentioned in the previous paragraph, then giving it a proper go will likely be a worthy investment of your time.