The Awkward Engineer, Trello, and Love of Physical Paper

Hi all!

I'm back. With an intent to be back weekly.

This post is about a dream I have to develop a perfect tool that marries the physical with the digital. In this case, I'm just talking about tools to manage my to do lists and notes. Things that I love about pen and paper include that:

  • it's always on and never runs out of batteries
  • it's distraction free
  • the resolution on pen and paper is fantastic
  • it unbelievably fast and responsive
  • it feels great

The problem with pen and paper is that it often fails to capture my workflow. It's a rare day where I'm afforded the luxury of making a single to-do list and then able to diligently work down it a single line item at a time. I'm constantly adding, subtracting, sorting, and editing my lists.

For a while, I made use of my personal magnetic Kanban board, but I found it just couldn't keep up with both my work stuff (I'm a technical program manager by day) and my personal stuff.



I tried using Trello, which does capture my workflow better (I've used it previously in small teams and loved it), but found myself struggling with distractions every time I needed to go online to use it. 

Queue the whirring sounds of invention. A ways back to using I'd hacked a script to use my thermal paper printer to print out my favorite comic strip every morning. The script broke when the underlying website changed the scraper, but I dusted it off, fixed up the script, and with the help of If This Than That and a command line Trello tool, I now have a fresh newspaper strip every morning with my personal to-do list for the day, including my calendar, the weather, and my favorite comic strip.

It prints every morning at 6:30am.



In particular, I love the morning weather report and calendar reminder because I don't need to check a smartphone, and also because I don't need to check a smartphone. (I have a love/hate relationship with technology. Mostly hate for smartphones.)

The simple, automatically printer personal Trello to-do list isn't enough to keep up with my work schedule though. I ended up with something much more manual and less snazzy than my morning news strip, but so far it's proven quite effective. Here's what I do.

  1. I have Trello set up with the following columns, which I find most accurately captures my work flow as a technical program manager. To-do, Today, Tracking (Ball is in someone else's court), Meeting Scheduled, and Done.
  2. I've juiced Trello with the Swimlanes extension for chrome. My three swimlanes represent Deep Work, which both requires intense unbroken concentration and is important, (i.e. writing a technical strategy document), shallow work, which is neither difficult nor important, and finally, medium work. Medium work is unique to the nature of a program manager job, where it's important, but not difficult, and usually means following up on an issue or keeping someone accountable.
  3. I take a screenshot of my Trello board as part of my morning routine and print it on physical 8.5"x11" paper.
  4. I quickly scrawl notes on the paper throughout the day and revisit it as priorities change, new things are added, or things get finished.
  5. Each morning, I transcribe my notes back into Trello, move completed items to done, and reshuffle my priorities. The transcription is usually just a few notes and it's not that difficult. The ritual of it is now part of my routine for clearing my head and planning out my day.



This has proven remarkably effective and it leaves a literal paper trail that I occasionally look back on to see what I've accomplished, or what I was working on and when.

The real dream, of course, is to truly marry the physical and digital, where I pair a whiteboard gantry robot with some machine vision so as you write on the whiteboard, it keeps Trello up to date and vice versa. If you want to sponsor that project or work on it, let me know!


p.s. For those who remember the old typewriter, I recently got my great-grandfather's typewriter refurbished and swapped it for my old machine. The typewriter repair shop claims to be the only typewriter repair shop in the New England region and happens to be the next town over. Apparently, business is booming. Anyway, my great-grandfather's typewriter is nearly 84 years old and still works like a dream.

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