Abandoning Trello

On the value of change and focus

I have been a passionate advocate of Trello almost since the day it came out. Visualizing the work is incredibly powerful, and its use of priority by ordering is so obviously better I could not imagine using anything else. I have brought Trello into companies, and caused hundreds of people to use it. Recently, though, I stopped using it in key functions, moving my personal tasks into Things and other work into the applications that own it. It started as an experiment, but quickly snowballed into a full transition as I realized how much better it would be for my core use cases.

I am a productivity junkie, from GTD to Deep Work, and while I know the tools aren’t the work, they’re one of the fastest and easiest ways to change a system, bringing new perspective and abilities.

I initially adopted Trello for managing my personal tasks. From there, it slowly spread to group and company use cases, and by the time I left Puppet in 2016 it was baked into our core business operations.

I had considered switching away from it for my personal tasks a few times, because it’s been obvious for years that it was not a fit for how I managed and processed my life’s flow of work. Where I had always taken great pride in my productivity system, I could no longer muster the discipline it required, which meant it was extraneous process and I was also failing to do my job. I sank so low that I began sending person to-do items to my inbox. shudder However, my life as CEO was busy, yet not really built around task execution, so it was never worth the cost of the tooling change. Or so it seemed.

While I abhor tooling changes for their own sake, sometimes you just have to experiment, and when I had a run of open space I decided it was time. Even if other places were worse, I was better off spending time elsewhere to get out of my funk than I was continuing to stare at this board that just wasn’t working for me.

As I looked to move away from Trello, I wanted to switch to OmniFocus, but the timing is wrong. I recently downloaded the current version, but it reminded me why I stopped using it years ago: It asks too much of me1. The biggest disconnects were the need for contexts, and the inability to set priority by dragging items around. It looks like the impending next version will be a great compromise for me, but I can’t use it until it arrives.

As I began moving tasks into Things, I was slowly reminded what it was like to have my task app be, well, an app. Before Trello I used Asana, at a time when its mobile experience was just a badly packaged web page. It’s been years since I had the pleasure of working with someone who bothered to build for the platforms I used. What a difference it makes.

Processing this small but meaningful change took over my brain for the rest of the day. I could not let go of the transition, but I also could not stop thinking about its consequences. “Thinking” is being too generous. I had not seriously looked outside of Trello for years; all of my habits and instincts are built within its constraints, its physics model. That meant wide open opportunity to construct whatever world I wanted, but also the need to do so, and embarrassing mechanisms for getting in and out. Creating a quick task in Trello is most easily accomplished by sending myself an email, which tells you how seamless the core experience really is. Telling Trello of work to be done in another application usually required custom applescripts to connect the two (e.g., creating message:// urls).

The keyboard’s change in utility keeps hitting me. I did not realize how rarely I used Trello shortcuts for their sheer disagreement with my hands. Well, partially, they were insane — ‘c’ archives cards, where I kept thinking it would create them, and repeating mistake kept my hands off the keyboard — but also, they were just different. I keep visualizing myself sitting at Things, fingers poised over the keyboard, in a world that makes sense to me. It’s pleasant.

I have a lot of work in Trello. Basically everything I’ve recorded in the last 4 years about what I could or should do is there, and it’s been the platform for organization all of that information. I’ve always been pragmatic, so even when I built it I would not have said it was the “best” answer, just that it worked at that time for my use cases.

Now I am questioning everything I’ve done recently — not to ask if I’ve made a mistake, just wondering what the world would look like if I had done that work differently. Are there projects languishing from sheer friction, that would suddenly become easier if migrated?

The answer in at least one other case is ‘yes’. I had a Trello board for managing all of my writing ideas, and I had a standard right-to-left workflow from idea to writing to done. I just never really used it. Instead, I did all of the management of writing in the same place I did my actual writing: Ulysses. I built a workflow from folders2 instead of lists3, and eventually I realized that the Trello board was hurting, not helping. The ideas I put in there languished, and Ulysses is just as good at capturing a sentence or two about a post as it is for writing the entire thing. The board is now closed, and my writing is in the same place as all of the work needed to manage it.

Tools do not make the difference, but tools can make a difference. A thing can go from undoable to tractable with a small change in tools, just as a math problem can go from impossible to trivial if you flip the equation around a bit.

I know Things won’t work for many of the use cases I have in Trello, partially because it’s so obviously a single-person tool, and much of my work does not have a home I can move the organizational work into. E.g., I have a list of lists in Trello of all of the day trips I could consider taking around Portland, and I can’t think of where I’d move that. I don’t know where those other problems get solved now. Maybe they don’t change.

But I know my standards have been reset. I know I made a mistake letting myself sit in one tool for years, unhappy but unwilling to invest in the change. It’s a wonderful feeling to be looking at the world through new eyes again.

  1. To be fair, I also stopped using it in the days when it took 45 seconds to open the app on an iPhone, because that’s how slow the data synchronization was.
  2. Which they call ‘Groups’.
  3. Really, are they any different?