The Awesome Power of Organizing Your (Digital) Junk Drawer
Creating a proper system for managing your tasks will free your mind up for creativity
This article was originally published on LinkedIn in July of 2021. I’m reposting it here as part of moving my writing to my own platform…
What good are containers with no system?
I never used to be a “note taker”... As a student, I was told that I had to take notes to succeed in school, so I took notes… Mom would buy me a Trapper Keeper or a stack of spiral bound notebooks at the start of each year, and I’d start the first week of school with the best intentions… Then by about October, I’d just stop… There will probably be a cosmic or karmic reckoning for all the wasted paper. Dozens of notebooks, now landfill… all about 20% used.
After graduation in 1989, I ventured forth into the world with a “business” degree, a suit and a briefcase… the degree, the suit and the case were supposed to impress people. My briefcase was a beautiful brown leather with my initials… A graduation gift from my now late Aunt Barbara. It was supposed to be for all my important notes and papers. As a tool for the working world of 1989 it was “OK”, but as a metaphor for my skills at the time it was perfect… pretty to look at but mostly empty.
Just like in school I was told that it was important to take notes in meetings. “It will keep you focused.” or “It will help you remember important tasks.” And, just like in school, my notes were pretty much useless. I literally spent decades fumbling my way through meetings of all types, writing things down that I would never look at again.
Two very important things set me up for failure in my education and in the professional world after school...
Nobody ever taught me how to take notes, so my notes weren’t very useful.
I had no way of finding anything after I’d written it down.
Picture a fresh faced young Rob in 2011... After many years of self employment, I had just started a full time gig with Lynda dot com. I was designing courses for video production and motion design and recruiting amazing instructors to work with our team to create them. I had way more inputs and meetings than I’d ever had in my life and I was drowning. A friend told me I needed to take notes… and then I told them a more expletive laden version of the paragraphs above. Then they said… “Keep your notes in the cloud and rely on search to find things... dummy.” Search for my notes using the words in the notes?
Hmmmmm, this whole cloud thing might just catch on with the kids.
Even though I’m a pretty tech savvy guy. I was relatively late to the cloud party. I’m definitely not an early adopter… Motion design and video editing are right on the bleeding edge of computing and I’ve spent enough time swearing at my technology to know that I’d much rather have other folks find the fundamental flaws in a new way of working. Trust my info to some magic computer sky god? No… thank… you.
Spoiler alert… the Cloud won…
Evernote became my go to app. EVERYTHING started going in there. Important strategy notes… check. Research on strategy… check. Notes from meeting about strategy… check. Shopping lists, receipts, weird fictional band names that pop up randomly in conversations, ideas for Linkedin articles, you name it. Pretty soon Evernote started to look like that drawer that every kitchen has. I could mostly still find things there but as my offerings to the magic sky computer grew I started to have a new problem… How the hell do I remember what I put there?
Uhhhh Duhhhhh Rob... You need a system!
Computers suck. Computers are amazing. Most of all though, computers are tools. And like any tool, they take time and effort to master. And, this next bit is reeeeeeeeally important… you need to have a systematic way of using them to accomplish your goals. In another article of mine I talk about the awesome power of getting stuff out of your head . Those techniques are incredibly important but without a system so you can find your ideas, the magic computer sky god will swallow them forever.
Uhhhh Rob… you know there’s an app for that?
Turns out there is an actual buttload of project and task management softwares and it can be overwhelming to try and pick one. Analysis paralysis is really real. “What if I pick the wrong one and I’m locked into some piece of crap solution?” In the 5 or so years since I started using a task manager, I’ve used Trello, Microsoft Planner, Notion, and now ClickUp. 4 app switches in 5 years. All I can say is that you WILL pick the wrong one. You can’t possibly foresee every situation… You can’t possibly anticipate every need down the road. You’re going to have to switch directions.
Each of those apps are amazing in their own way and they each suck in their own way. In a previous long winded draft of this article, I dove into pros and cons of each of these, but I cut all that junk because the list of pros and cons would just pass on the analysis paralysis to you, the reader. If you have one takeaway from this article let it be this…
Software doesn’t really matter.
I realize my friends in the software industry are now going to leave flaming bags of crap on my door. But let me clarify/backpedal just a bit… The software you pick isn’t nearly as important as your system. You need to figure out HOW you need to work before you can choose any software at all. Software is a tool and you need to know WHY you’re using a tool before the tool becomes useful.
To develop a system that would work for me, I needed to think a lot about my process, and how I function from day to day… In my world the basic unit of currency is the course. Each course is a project with a predictable flow as it moves from an idea on a list to a real thing that people can watch in the library. But courses are created by people and I need to also remember what I talked with them about. What I need is a way to track the course, the conversations with instructors about that course, the notes I create about the course and conversations as well as the tasks I’d have to complete to bring that course to completion, and I need a way to tag things for relational linking and making the search easier. It sounds simple, but it has literally taken me years to figure that out.
Projects, Tasks, Notes and Tags OH MY!
The problem now is that there is no one software to rule them all… Evernote is fantastic at writing long text notes, but it sucks for task management. Trello is good at tracking the individual courses and instructors but not good for relational linking between those elements. Planner is an incomplete copy of Trello. Notion is a completely open system with every conceivable feature but you have to build everything from scratch. It’s a tool for obsessive people who love building tools. That is definitely NOT me. I have better stuff to do. So that leaves me at ClickUp. I’ve only just started using it, but so far it “feels” like it might work. But so did Trello, Planner and Notion LOL…
I don't want to bore you with the details of my system, but I've broken things into two big categories... Work and Personal with subcategories under each based on the big things I need to focus on. For Work it's stuff like "Roadmap" and "Instructors"... For Personal, it's stuff like "Non-Profit Projects" or "Articles"... Everything not directly related to my day job.
The system I’ve created mostly works, but only time will tell. An organization system is just like a diet or an exercise plan. They’re only as good as your ability to stick to them. At the very least, building this new system has been a good way to climb out of the dark places that COVID and 2020 took me. For most of the last year and a half I’ve been in “reaction mode”... Not really looking ahead. Just trying to get by with my sanity more or less intact. In addition to the chaos of the world I’ve been going through tremendous changes at work and developing a solid system has been a way to counteract that feeling of helplessness that comes from having change imposed on me.
This process is empowering. The exact opposite of the last 18 months. What are YOU doing to get YOUR digital junk drawer organized?
(Also, if I get enough requests, I'll record a short video tour of my ClickUp system and post it here on Linkedin.)
(Also Also before you ask, my actual junk drawer still isn’t organized.)
