The New To-Do List: why I’m back to pen and paper
I’ve always loved tinkering with my digital setup. Since I got my first computer, I’ve spend countless hours playing with software, looking for little hacks, and always in search of better organizational systems and file management. Every so often, I’ll swap my preferred text editor for another to see how I like it or try a new app to see how it fits into my workflow. Lately, this tinkering has focused on to-do list applications and project management software.
Since transitioning to full-time self-employment, I’ve had to take stock of my own workflows and reconsider how I manage tasks and track time. For the better part of the decade, I’d been a loyal Things user. I first downloaded it in college and have used it through every job I’ve had and grad school, as well as keeping track of personal and household tasks like taking out the trash, watering plants, and grocery lists. Last year, I switched to Wunderlist in an attempt to better manage multi-part projects and keep track of freelance projects. Over the last few weeks, however, I’ve started using another system that, albeit strangely, has become one of the best task managers I’ve used: pen and paper.
The biggest challenge I faced when I started working for myself was time management. Without working on a team, I didn’t have as many meetings I was working around and suddenly found myself managing my own projects, assigning due dates, scheduling phone calls, etc. My work generally falls under three categories: client work, teaching, and podcasting and when I first started working on my own, I found the best way to manage my time was to split these up by day. I’d dedicate a day to preparing for class, a day to schedule, record, and edit podcasts, a day for one freelance project, and so on. Tasks would be added to Wunderlist and assigned due dates that correspond to the designated days so when I’d sit at my desk in the morning, I’d see everything I needed to accomplish for that project each day.
But a few months ago, as my teaching schedule increased and my freelance business started to grow, I realized the rigidity of that schedule was limiting. I was be much more productive — and move projects along quicker — when I worked on multiple projects each day. The problem with this is that tasks would go into the to-do list with a single due-date and would only show up on that date. But sometimes I don’t have specific tasks that need to get done each day but I want to make sure I’m working on this set of projects each day, just moving them forward. I could set Wunderlist to notify me a few days before the due date, but then I can’t check it off if I spent time working on it, because it then marks it as complete. I still want a record of each day I worked on a project even if it isn’t finished or due.
What I’ve started doing is dividing an 8.5x11 piece of paper into six columns: one for each day of the week with an extra column for miscellaneous tasks.1 In each column, I write down everything I want to work on that day. That can be anything from the people I need to email, specific project sub-tasks, or even just a project I want to spend time thinking about or working on generally. With a red pen, I copy everything from my calendar into the columns — classes I’m teaching, scheduled podcast interviews, meetings, etc. along with their times. When tasks are completed or finished, I cross them out. This paper sits on my desk where I can clearly see not only my schedule but a rough outline of everything I’m hoping to accomplish for the week. The problem with this — and it’s a problem I have with every to-do application I’ve tried — is one of input. I spend the beginning of the week writing down everything I want to do. Even when I’m fully invested in a task manager, the problem isn’t the to-dos, it’s remembering to put the to-dos in the app. I have a bunch of recurring tasks still in Wunderlist that notify me each week for things I always need to do (edit episode, write this week’s class lecture, etc.) but those don’t account for multi-day projects or one-off tasks.
So what do I want in a to-do list application? I want to combine my crude pen and paper system with the recurring functions of a Wunderlist or Things. I want to be able to clearly see what my week looks like and how I’m dividing my projects across the week, what I need to spend time working on each day. What I’m looking for, I guess, is a non-time-specific calendar — something that merges my schedule with my tasks — and let’s me see the week at a glance, pulling in recurring tasks automatically while allowing me to fill in and divide my time for other projects, making for an easy record of everything I worked on each day and each week. Does such a thing exist? What to-do apps are you using? Is there a better way to do this? What am I missing?
Our systems are very different, but Craig Mod’s calendar system was an inspiration, and another example of an analog calendar/to-do list. ↩