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Task Manager Burn & Build Notes

Image of a burning forestI started what I call my Task Management Burn and Build about a month ago. I’m still not completely comfortable with where things stand now, but it’s time to stop fiddling and try to settle into my new task management workflow and see exactly where it falls short. I’ve come across a few things worth noting. While they won’tt apply to everyone, I’m sure they aren’t completely unique to me.

Please, I Want To Pay

If I’m going to use a software or service to run my business, and life, I want to be sure it’s supported and around for a long time. So not only am I willing to pay for the software or service, I consider it a positive feature that enhances the product.

Of course, there has to be a value proposition that’s in my favor or at least equal. For example, Asana and Trello were very similar in the way I was using them. To get the features I wanted from Trello would cost me $40 a year, while the free level of Asana has all the features I would need. The least expensive paid level of Asana is more than I would be willing to pay, especially since it doesn’t add any features I would use. While Trello did seem to be a slightly better fit for me than Asana, I also thought a little less less of Asana because I wouldn’t be paying for it. Free wasn’t something that added to Asana’s ability to pull me in. If I find, after a year, that I’m not using Trello enough to justify the cost I might switch to Asana. If I can’t justify $40 a year then the service wouldn’t be integral to my workflow and free isn’t a detriment since I wouldn’t suffer it it went away.

Software & Services Can Go Away

Similar to wanting to pay for a service I use, I also want to make sure that the software or service has a business plan. I’ve never committed to If This Then That (IFTTT) because they didn’t have any visible business model. They implemented one recently but it doesn’t seem all that robust (or profitable). My fear would be that they either just fold up, or get bought up and radically changed.

Zapier is a smilier, but more robust, service like IFTTT. They also have a limited free level but have subscription plans. While Zapier could certainly go away I would lean towards using it because I view them as more stable. But as I said above, there has to be a value proposition in my favor and at this time I can’t justify the cost of a Zapier subscription.

Of course, any software or service can go away. So I try to keep data in a format that’s transportable between different software and services. Unfortunately this doesn’t seem to to be a viable option in the task managers that I looked at. Some do have import/export options but getting compatibility between different applications could be a major effort and not something I would count on.

One Size Doesn’t Fit All

I’ve always tried to keep all my task and project management in one application, which was OmniFocus for the last two years. As I experimented with my new task workflow I came to realize there wasn’t one application that would do it all. Picking one app would mean that I would lose certain features and abilities. As I looked through other apps it became apparent that if I wanted to use just one app then that would mean staying with OmniFocus. And I already knew that OmniFocus was falling short.

OmniFocus is Apple only, iOS and Mac OS, and it can’t be shared with others. While there is more automation around new versions, getting tasks into OmniFocus typically requires more steps.

Todoist makes it easy to get tasks into it. There’s a lot of integration with other web services including IFTTT and Zapier. OmniFocus provides no real integration although tasks can be added using email if the OmniSync service is used.

While templates can be created for Todoist projects, I can’t leverage them because I don’t have very many standard projects. So I found it tedious and time consuming to add medium to large projects. Making this worse was that the way Todoist handles subtasks just doesn’t work for me. I tried several alternative methods but none really clicked with me. (In short, subtasks can’t be set to repeat with the parent task. They appear as done when the parent repeats. If they are set to repeat on their own they immediately re-appear with the new date when marked as complete. This makes it hard to quickly see what still needs to be done.)

On the other hand I like the ability to plan visually with Trello, especially for larger projects. But I have a lot of shorter projects (usually recurring) or a single task that needs to be repeated on a weekly basis. I found Trello cumbersome for these short and single task projects. They could be done, but it was always uncomfortable and I never lost the feeling that I was forgetting something.

While Todoist could share projects I found Trello easier for others to use. Even if they weren’t familiar with Trello it was easy for them to go into Trello and see where the project stood. They could do this with the free plan and it’s a good way to keep others updated.

Current Status

Eventually fiddling with task apps becomes counter-productive. I’ve settled into a system which seems to be working for me. It was kind of an accident, although it was a bit intentional. As I set up new projects in Todoist and Trello I saw what worked and what didn’t. The same happened when I moved projects from OmniFocus to Todoist and I did encounter some workflows that failed fast. Since I hadn’t deleted the projects from OmniFocus it was easy to move back as I tried to find a solution.

I’m currently using three task managers. Just writing that makes me cringe since I think thats’s two too many. But things settled into a natural order and I think it’s made me more productive.

Todoist has settled into the role of the task manager for my personal tasks. Since I work for myself there’s a group of tasks that can be either personal or business. For example, is reading tech articles personal or business? I used to think that if I had two task managers, one personal and one business, I needed to properly classify each and every tasks. Instead, since it’s easy to get tasks into Todoist I use it for tasks that come to me during the day. These are mostly personal tasks and a few that fall into that middle ground.

Even though I now have two task managers they naturally split my tasks in a way that allows me to mode shift in a productive way. During the time I consider my workday I use OmniFocus and only OmniFocus (OK, occasionally Trello for planning or to update others, but mostly OmniFocus and never Todoist). The work I do at my desk (or what passes as my desk if I’m on the road) and work related to a customer’s project are in OmniFocus. This keeps me focused on my business projects. I don’t even see my personal tasks since Todoist isn’t even open, so there’s nothing to catch my eye and send my down a rabbit hole. The vague personal or business tasks aren’t anything that needs to get done during my workday so being in Todoist isn’t a problem. They are typically articles to read, emails to answer and similar things which I typically do after my workday, or for a limited time during lunch.

So multiple task managers has helped me focus and remain productive during the day. Another benefit is that I’m no longer checking off completed items in OmniFocus during the day, or if I am it’s because of progress towards a business goal. When everything was in OmniFocus I would ofter check off a number of small personal tasks that didn’t make progress towards a major goal. Despite not having any substantive progress I would feel like I did a lot and could relax, after all I finished 10 tasks from my list. That made it hard to stay focused and motivated.


The big lesson for me from this burn and build is that not only don’t I need one task manager for everything, I’ll be more productive and focused using two. It helps me keep my focus in the right mode, business or personal.

I’m still looking for a way to replace OmniFocus since it’s not cross-platform. This is less critical now that I have other apps in my system so I won’t dedicate a lot of time to the search, but I will remain on the lookout.

Todoist is working well, but I’m not optimistic that it will be changed to eliminate where it falls short for me. I don’t like the way sub-tasks work but it is a valid method and I’m sure there would be many complaints if it was to change.

I’m sure I’ll make some tweaks over time, but for now my task management system has been rebuilt and is ready to use.