I digitally journaled for 600+ days: here's what I learned

For full disclaimer, I didn't start out as somebody who journaled, or kept a personal diary. The most I've ever done physical journal-wise was doing product mockups/sketches in my early days (before I discovered Excalidraw). For a few reasons, this changed:

Years ago, I found and was inspired by Benjamin Franklin's calendar, which gave me some idea of an initial hook or anchor - his two questions, "What good shall I do this day?" and "What good have I done today" are really good general questions.

So for the first few months, that's what I did! My journal literally looked like:

For a few reasons I'll highlight later, this was not the final format.

(You'll notice I use body hashtags: because I use Obsidian for my journaling, it supports markdown files, hashtags, etc. - essentially creating a graph of your work. I wanted to leverage this, but I found the body tags a bit frictionful for my purpose.)

Nevertheless, I persisted in journaling for a few months. This was 2023: the same year I took a big summer trip to Europe. I took a one way flight because I intended to adventure on my own timeline, and I was already on hiatus after my last engineering contract ended.

There was something magical about that trip that inspired me: over the course of two months, I traveled to Greece, Italy, Switzerland, Germany, the Netherlands, Portugal, and the United Kingdom - with stories for another time. This particular photo is from Switzerland (Lake Bachalpsee)!

Upon coming back, my mentality had shifted. Never had I witnessed such beauty in my life before, and I wanted to do everything I could to witness such beauty again - to have the fitness and financial well-being to visit again over and over.

My mind was set on deliberate habits and goals - and for this, I wanted a far more sophisticated and detailed version of my journal. There's something about all that hiking which made me realize: the best systems are the ones that work for you without being forced.

That's where I drastically reworked my current journal into four sections:

So the body format became:

I dropped the body hashtags, because that gave me friction to writing my thoughts, and I figured: frequency over intensity. I can also search in Obsidian if I need to.

Over the course of my current journal's lifespan, I've gone through five startups, visited Switzerland again, attended my best friend's international wedding, built three of my own products solo (I just released Truly.dev, btw), started working out every day, lost 60 pounds, broke up with my girlfriend, and strived to become the strongest I could be in all facets: mental, physical, and spiritual. Awareness is a hell of a drug.

There’s an example I love. If you take off from New York, and you’re heading to Los Angeles: if you’re one or two degrees off, you’ll end up dozens of miles away from your intended landing spot. We as humans do this every day - with ourselves, with our goals, with our dreams. Some people like to check in with themselves once a month, once every so often, but I like to make it as daily as possible.

I think overall, it's been a delightfully solid format: 600+ days later, I've evolved it only a little since then (additively): I'll cover those bits (and more) in the next edition. I got an incredible look into my own mental processes (even graphing them out), and I can stack my wins daily much easier now. I can also look back historically and understand my thought process at a given moment much better.

If you want the full journal template, the copyable daily template I use -today- is below, as well as on GitHub. You can paste this directly into Obsidian, and it will work out of the box. You’ll notice this is in Markdown format, but you can strip it for whatever format suits you best. The importance in journaling is finding the way -you- enjoy!

To configure it for one-click daily notes (the way I do it), you can check the Daily Notes functionality in Obsidian.

By the way: if you’ve read this far and enjoyed any part of it, I’d appreciate you sharing to colleagues/peers and subscribing. Much like how I journal daily, I’ll be writing here weekly. Feel free to connect with me and tell me what you like and want to hear more of!

Be well,

Michael Kirsanov