To Do Today: The Evolution of My Daily Planner

In my last post I talked about systems being a spiral that pull you upward with every loop.

Looking back on my own system while doing research for that post, I looked at how it evolved through the years, and how my own life as a remote worker went from forcing myself to beat procrastination to pacing myself and not taking on too much at once.

I put together snapshots of how my daily planner looked like over the years as a representation of how a system evolves.. I hope this serves as inspiration.

Hundreds, if not thousands of post-it notes scattered through apps like Google Keep. These aren’t plans, most of my thoughts went directly into conversations (email, internal communication at work) and I only used my notes for streams of consciousness and drafting.

I was all about task management. I lived by my to do app (Todoist), having a ton of automations, recurring tasks, items that got created automatically from events and even triggers like missed calls.

This was great for doing individual tasks, but as I used this system I found myself just wanting to tick tasks, without having larger projects and goals in mind.

I moved to Notion as my daily driver, and focused on getting projects done. I avoided being task-oriented so much that I ended up not planning my days at all for a while and just working on these long documents instead.

As mess piled up in my notes, I saw the proverbial things falling through the cracks more and more. After a while, I decided to start working in weekly and monthly cycles.

This is where I fell for "Productivity Porn." I built dashboards, rollups, and complex databases. I spent more time tweaking the system than doing the work. This was the opposite of digital wellness.

Notion became a (pretty) burden, demanding my attention rather than supporting my life. I had created a system that required more energy to maintain than it saved.

Since 2023 I’ve been using Craft Docs, and in the beginning my daily page was equally polished. However, it started to grow more and more functional the more I internalized a way of working that got things done.

Today, I have the most lightweight daily planner I’ve ever had. A lot of the things that I do in a day don’t need to be planned, since I no longer need to force myself to do them, and my routines are balanced enough that I don’t forget to do parts of them.

In my weekly planning session I usually put the most important things I want to work on, pre-fill meetings where I jot down the agenda and meeting notes, and leave a lot of space for the unexpected.

I don’t think any of my older approaches were wrong. They are wrong for where I am in my journey now, but perfect for where I was back then.

When I started life as a remote worker, it was tough to push myself to do the things I had to do. The more I did push myself, the more motivation left room for discipline, and I no longer even felt the need to push at all.

Nowadays, I focus on leaving room to breathe, unwind, and disconnect. I know I don’t need to be working 14 hour days, and I know how bad my output is when I do, so I use my planner to make sure the things that matter get done first.