Trials and Experiments

There are many times with many things where I can be afraid to try something new. Trying something not in my comfort zone can be downright frightening. Other times, I’m plagued by the friction that comes from doing the new thing. But for all of the reasons not to do it, I still want to try them: I’m curious about new things, new possibilities, and wonder if there are better tools out there for me to use. And I’m easily distracted by new, shiny things.

Recently, tried using new task management apps.1 There have been updates to several apps, most notably Todoist and OmniFocus. I wanted to see what benefits they could offer me over my current app, 2Do. There was a huge group of people that really started loving 2Do on iOS. Many users switched over. But for many [private] reasons, there had been a slowdown in development. And I’d be lying if I said it didn’t worry me a bit; after all, it’s one person doing the entire app.

So in this slowdown, I wanted to experiment to see what else was out there. The first point of friction was moving select things over; most apps don’t have easy ways of export/import. The second was the nomenclature: can often get lost with naming conventions until I have an equivalency to something that I know, something that is familiar. With those things out of the way, I could try doing things in a new way.

There were things about Todoist that I really liked: clean UI, collaborative tools, and the ability to enter in tasks for work via the Chrome extension. And while this felt OK and I spent a few days with it, it didn’t feel right. I don’t collaborate with many people on tasks, and when I do, it’s usually work and I need to go see them anyway.

So I once again tried OmniFocus to see if the new changes – especially to the input method via TaskPaper format – would work for me. The taskpaper format is really interesting, when it works well; it was cumbersome to get right, however, which is probably due to my lack of knowledge of TaskPaper more than the feature itself. I also dove into the MailDrop feature, and it’s fantastic: the ability to set email addresses, even as a temporary one, is great. And I definitely missed the Forecast and Review features, both of which are top notch. But one of the big things that I had difficulty with was the lack of batch editing. It made it very difficult to move a huge Inbox full of tasks to one context or another, and is something I cannot fathom as to why it’s not implemented yet.2

So after spending some time entering in all my tasks to other apps, I was met with a notification when I got home: 2Do beta v3.8.3. Couldn’t really have been timed better, huh? After a long period with no updates, I was happy to see the improvements, offer some suggestions, and talk to him about the ones to come. Most importantly, I needed to implement them into my daily workflow.

Initially, I was upset with myself for wasting time: why had I spent the effort to move things over to different systems, only to find that my current app was what I needed? I have things to do, and messing around with my task management system shouldn’t be one of them. I felt like I should have said “I’m sorry”, like trying to convince an ex-girlfriend to get back together after taking a break to see what else is out there.

But…

It was actually the best thing I could have done. What this has shown me is invaluable: ways to use my current system that are even better for what I need. There were positive things of these other apps that I tried, and fortunately, I can bring a few of them over using the current feature set.

A prime example was something that I completely missed when Email 2Do was first launched: if someone sends me an email to a specific email address, they can send me a task. Even better, if my wife sends me an email with the subject “Groceries” and puts a numbered list in the body of it, now I can get the shopping checklist right there in 2Do without any input from me.3 I’m hopeful that with future updates, that there will be the ability to add more functionality to Email 2Do, so that there can be more detail added like due times, tags, locations, etc. I can see this being useful for when I get a grocery list and have to get something after I leave work.

Another thing I learned in this experiment was that I was over-tagging and over-searching. I had too many tags that I was using to identify tasks. If I have a task in the “Home” list, why do I need to tag it with “Home”? This is completely redundant. And I really only need a handful of Smart Lists, not the 10 that I previously had. I completely rebuilt my work tasks from the list I created when I moved things to Todoist and OmniFocus, and had a better understanding of what needed to be accomplished for each of my four programs. And I also am now sparingly using starred or priority tasks, reserving them for only the highest of importance. All of this has helped me clean up my task list and get more focused.

The biggest thing I’ve learned from this: fundamentally, at my core, I’m a broken person. I do a lot of this to myself. But I accept it’s in my nature to always wonder if the grass is greener, and spend my time playing with new things when my existing thing works perfectly well. Having gone through this, I can see where I can make changes, and build my tools in such a way to make them work better with my current thing than I did before. And even though it may take some time and effort to do these things only to find them futile, I learn a lot new methods, better ways to use my current system, and clear out the stuff that isn’t really important.

Conducting a trial of apps was a great exercise, and I’m glad I did it. It was painful, but rewarding. I learned a lot, rebuilt my paradigms, and I learned how to do things better with what I have. And that’s a great feeling.


  1. “But you literally wrote a book on 2Do!” I know, I know… hear me out. 
  2. I hope that this comes soon for iOS users. This is by far one of the biggest complaints I have heard amongst my friends who use OmniFocus. 
  3. The hardest thing at this point would be getting her to use that, not the Reminders integration we use in AnyList; I think we’ll be sticking with AnyList for that purpose for the foreseeable future… 

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