011: Picking a Task Manager



This week, Justin talks through the thought process of picking (or changing) a task manager.


00:00 Hello and welcome to Process. My name is Justin DiRose, owner of the Productivity Guild and today we’re talking about picking a task manager.

00:09 Before we dive into this week’s topic, I wanted to give a quick update on the Making Sense of Bear course. The last couple of weeks I’ve been working hard at developing the outline of what this course will look like and all the different topics that we’ll cover and I’ve got it to a point where I’m ready to start recording. So this week we’re going to start recording videos for Making Sense of Bear course and when those are ready to go there’ll be posted on the Productivity Guild for our Pro members to take a look at. Now if you are interested in purchasing this course, it will be available for purchase as well and you can head on over to productivityguild.com/bear to get all the information for that. Now on to today’s topic. One of the challenges in productivity is figuring out just how to manage your tasks. There are a million different applications out there for this and there are a million different ways that you can use them on top of it.

01:01 So it gets a little challenging to try to figure out how do I pick the right tool for me. And so today we’re going to talk a little bit about some strategies of how you can do that. But first I want to dive into the topic of what is a task manager. Well, as the name says, a task manager manages tasks, but as we all probably know from school, it’s not really great to try to define something using the words itself. So if we look and take a step back, let’s define a task. A task is really something you could do. It doesn’t necessarily mean that you’re committed to it. It doesn’t necessarily mean that it’s something that you generated yourself. It could come from somebody else, but it’s something that has been put in front of you or is in your mind that you could do.

01:43 A task manager, therefore, is a place where you put tasks, those things you could do to process them, and then store the ones you intend to do later. See there’s a difference there. A task manager is most effectively used when you put items in there to process them and you have a system to handle those items to determine the ones that you intend to do and the task manager is to store the items that you intend to do later. Now later can be 10 minutes from now, later can be a month from now. It can be a year from now. The whole point of a task manager is to become a sort of a second brain for the things that you need to do so that you don’t have to remember them all in your head. Another advantage of a task manager is that it helps you make decisions in advance.

02:28 I mentioned this in a previous episode, but one of the ways that I’ve learned to think about a task manager is that anytime you add metadata to a task such as a due date, a flag, a tag, add it to a project, you’re making decisions in advance about what that thing is and how you’re going to handle it in the future. So for example, if I’m making a project inside of Omnifocus for recording this podcast and getting it published, I have some decisions to make an advance about how I want to handle my work process. So I can take that and I can set it as a sequential project, which means only the first task in that list will be shown as available, which means I’m going to work on this project in order. Whereas if I put it as a parallel project, one of the thing I could do there is I could work on all of those tasks in any order I want or at the same time. I can add specific tags for the different modes of work that I have and I can assign a due date to the project to say, Hey, this needs to be done by Friday morning so it can go out.

03:28 These are all decisions about what this project is, what these tasks are and how I’m going to handle them in the future. It’s one of the main benefits of using a task manager is that there’s usually fields in there are ways that you can add metadata to a task to tell yourself in the future how you want to handle that task. I think in some regards, the task manager is one of the most important pieces of someone’s workflow in productivity, especially today with the flood of information that we deal with on a day to day basis. When we have systems in place that help us take that information and process it, throw away the stuff that’s not important or essential and focus on the stuff that’s essential, then those tools become really valuable. The struggles with task managers longterm is keeping the essential stuff in there and getting rid of the stuff that we don’t.

04:14 It’s very easy for stuff that we don’t need to start to clutter up in our task managers and that’s why we need things like weekly reviews and stuff like that. So now that we have an idea of what a task manager is in this type of role that it plays in our lives, what are the different kinds of task managers out there? I’ve broken these into about five different categories. There are probably a few more, but these are the general buckets that task management type apps or systems tend to fall into. The first one and the one that’s gaining a lot more traction these days is analog. These are things like just having a notebook and writing your tasks down. Things like using the Bullet Journal system or the autofocus system. The benefits of having an analog task manager is that you’re disconnected from technology.

04:57 It means you’re not going to get stuck in fiddling in a tool all day long or trying to figure out how to get something to happen inside of a piece of software. It’s also flexible. You can lay out your tasks any way that you want to on a page. Some considerations with paper though are there are no notifications, that it can be difficult to manage repeating tasks, and if you have a lot of stuff that you’re storing in your notebook that you’re looking at such as lists or recurring projects or processes, and then when you fill that notebook up, then you end up having to recopy that to another notebook. So there’s a lot of manual work involved with having a notebook or analog based system.

05:36 The next main category of task managers, our list apps, these are apps like Apple Reminders. Remember the Milk and Microsoft ToDo. They have some extra features added into them, but their main focus is creating simple lists. And that’s one of the main benefits of these lists apps is that they’re simple. They don’t have usually a lot of fluff. They don’t have a lot of complex features. They just are there for making lists. They usually sync really well and they’re perfect for smaller workloads. Some considerations for list apps though are there’s not usually much metadata for tasks in there. Most lists apps don’t throw in anything like contexts or tags and the UI in these apps usually aren’t designed for speed or ease. A lot of times deeper features tend to be hidden in these applications to make these applications more approachable for people who aren’t necessarily into making things more complex, so they tend to hide things like iOS Reminders is one for example that I tend to think of that it can be fairly tedious to add a due date or a priority or something like that to a task because you have to create the task and then you have to go into a special menu and deal with it that way. It just gets a little bit complex and it’s not super speedy, but for people who do need just that little simple application, often oftentimes Reminders is perfect for those use case.

06:54 Another level of task manager are the ones that I like to call the project manager. These are usually what we think of when we think of a task manager. These are apps like Omnifocus, Things, Todoist and GoodTask. These project managers can handle a lot of tasks. They usually have some sort of builtin process or flow that’s designed into the user experience to help people process through their tasks. They usually have some kind of an inbox where things can get collected and then get deleted or delegated or sorted from there. Also, these project managers tend to be fairly highly customizable. That can be from automation. It can be in like in the case of Omnifocus, custom perspectives or basically custom ways to filter your lists, to create new lists. But some of the downsides of these project managers is that they can be very complex and to customize them can be really fiddly. You can spend a lot of time in customizing these apps and often they’re expensive and so project managers are usually tools that you don’t jump into unless you absolutely have decided that you need those.

07:59 There are a couple other categories of task managers that don’t necessarily fit into the traditional three that we just talked about: Paper, List apps and project managers. There are a few new ones that are starting to surface with the advent of Web apps and collaboration and that’s actually our next category or the collaborators. These are applications like Todoist. Now keep in mind Todoist was also mentioned under project managers but one of Todoist’s main features is that you can use it to collaborate and assign tasks between people.

08:30 Other apps are Asana and Nozbe. The benefits of these apps are they’re designed with collaboration in mind, meaning you can have a whole team on an app like Todoist or Asana and then you can assign tasks to people throughout that. It’s really helpful to keep your team collaboration in one place. And another benefit is that these are usually cross platform so if you have part of your team that’s on windows part of your team that’s on Mac part of your team that loves iOS, you can usually function pretty well with these. Some considerations here though is that cross platform user experience can be either wonky or inconsistent. I’ve run into this with applications like Todoist. You have one experience in their web application. You have one experience in their Windows app and another experience on their Mac app. Other applications like Evernote have run into this as well. Some of these tools can be restricted to a web app or their web app is fully featured and their mobile apps or their desktop applications have fewer features than the web app, which can be a little difficult to deal with at times and again. For some of these, since they’re a team based solution, oftentimes they cost per user depending on how many people you’re trying to get involved in this task manager, your per user costs can add up.

09:45 The last category here are multipurpose apps. These multipurpose apps have been around for a while though. They’re starting to gain a resurgence with some new players on the scene. Evernote has been in this camp for a long time branding itself as a task manager and note software where you can just put anything you want to in it. And another new player that’s gaining a lot of traction is Notion. Benefits of these tools of that you have everything in one tool. In the example of Notion, you can have your tasks notes, project reference materials, calendaring and all of that in one tool. Same thing with Evernote. You can have all sorts of reference materials and tasks right together and even the same note. These tools tend to be cross platform as well, which is hugely beneficial. However, some considerations here is that often data is held in proprietary format, meaning it’s a little difficult to export things once you get them in. So this is something to consider if you don’t want to get locked into a particular platform. Additionally, all in one tools can have a great overall experience, but they can suffer in particular areas because maybe task management isn’t something that they’re fully focusing on developing, but they’re really want to develop this note taking piece over here and task management is sort of an add on. Something to consider with these.

10:59 Now, with any of these categories here, it’s important to find something that works for you, but how do you choose a tool when you’re first starting out? I personally recommended try paper to start off with, or if you absolutely don’t want to touch paper, try a list application. The reason being is that the simpler solutions give you a feel for what you need and you don’t in a tool. In fact, many people these days are getting by with paper alone because systems like the Bullet Journal are just enough structure that people need to be able to manage their lives. That’s really the key. You’re looking to find a balance of what you need in a tool with what you need to manage your life. Sometimes we jump straight into something like Omnifocus or Things and then we’re like, whoa, this is way too much or way too complicated and that’s, that’s okay.

11:45 Like sometimes we need to explore a little bit and figure that out. But in order to maybe avoid some difficulty and pain that comes with that, that’s what I did, I jumped straight into these big shot applications instead of trying to keep it simple first. And it’s honestly slowed me down over the course of years. It’s taken me probably, you know, a good six years or so to get solidly familiar with a tool like Omnifocus so I can actually use it effectively. So if I had started with paper or, uh, more of a list making application, I think that I would have felt the need to switch to a tool in a little different way because I would have started about my system versus the tool. And that’s what, that’s ultimately what it comes down to a task managers is that it’s not about the tool that you use, it’s about your thought process and using the tool.

12:29 And it’s about ultimately figuring out your system around the tool. Because at the end of the day, you’re the one making decisions about what you’re doing, your task manager isn’t. Your task manager is just an application that’s there holding data that you put into it. And so when you can define your system up front in a simpler context, you can then build upon that in a more complex tool if you need to versus trying to figure out a system and a complex tool at the same time. What if you’ve been in a task manager for a long time and what you have right now isn’t meeting your needs? Maybe you bought into Microsoft Todo after they acquired Wunderlist and you’re realizing that your workload has increased and and that application just isn’t cutting it. Or maybe you’ve been a paper fan for a long time and you’ve been trying to figure out like, gosh, I just keep forgetting these things and I don’t really have a way to remind myself of them.

13:20 How do you handle that? I mean we, we all grow in our needs for managing tasks and our needs and lives. So how do you handle those changes when you’re starting to feel that friction? First thing to do is look at a way that your tool now can maybe handle those needs. You don’t necessarily have to jump ship on the tool that you have. You might need to just rethink the way that you’re approaching the tool. So for example, if you’re having trouble with paper not notifying you, do you need to fully jump into a tool like Omnifocus? I don’t think you do. You could first say take a hybrid approach to the problem and incorporate an application like Due on iOS, add your reminders that you need in there. Let’s say like, Hey, I got to take the trash out every week Thursday at 7:00 PM and if you keep forgetting to do that, use Due to remind you to do it.

14:11 That way, you don’t have to shift off of paper. Or if you have a lot of recurring lists that you need to handle instead of managing them on paper and trying to copy them over, keep them in a digital tool. You could use something like Bear. You could use a simple list application to manage those lists and then you can still keep using paper for all of your day to day task management and project management. The key here is that you don’t have to keep everything in one tool. Just like we talked here, like many folks use multiple apps for different purposes. I’m one of them. I use Omnifocus for my task management. I all my project management, I try to keep everything that I can’t remember inside of there, but it’s not encompassing everything because I also use an application like Reminders for my grocery list.

14:55 I also use paper to manage my day to day task list. It’s just a matter of evaluating what you need. Additionally, you might need to ask yourself some questions about how your tool is working for you. If you’re not able to see something in your tool, maybe there’s another tool that does it better or that has a feature. So for example, you’re looking to see your tasks that pertain to writing, but they’re across multiple projects and your current tool doesn’t allow you to see multiple projects or multiple different types of tasks across multiple projects. At that point, maybe a project manager that has tags where you can tag all of those tasks with writing may be a better solution for you because that task manager can pull all of those lists and all those tasks into one list. So ask yourself, what do you wish you could see in your current system, but you can’t now due to technical limitation.

15:45 Additionally, ask yourself, do I need to collaborate and assign things to others? If you do, then instantly the collaborators group comes on the table as an option. Things like Todoist, Asana, and Nozbe. Lastly, this is something we don’t always talk about because we tend to see people progressing into task managers instead of out of, but I think something important to ask is do you need to scale up or scale down in your task management usage? If a tool like Omnifocus or Things is getting too much to manage, do you need to step down and use something like a list app or even paper? Sometimes our tools can be the source of stress or the source of difficulty and it can be because we’ve overcomplicated things, we’ve added too much into our system than we actually need and I’m not talking about tasks.

16:30 I’m talking about the actual features and usage of the tool. This is something I’ve honestly wrestled with myself in regards to Omnifocus. I love Omnifocus. It’s a fantastic tool, but I’ve gone through the last couple of weeks and wondered is this really the best tool for me? Could I get by with something less expansive, less complex? Now granted, I’m probably not going to switch away from Omnifocus because there are so many features in there that I do use such as automation and project templating through taskpaper that I don’t foresee myself leaving that anytime soon because I find it so useful. But there are other ways where Omnifocus is a little too complex at times. So to sum it up, as far as picking a task manager, if you’re just starting out, start with paper or something simple. Build your system first. Build your mindset toward task management, and if you’re in a situation where you’re feeling like your tool isn’t meeting your needs, evaluate if there’s some, some way that you can augment your tool right now to get what you need without completely switching away from it.

17:28 And if you do find that you need to switch away from it, start asking yourself some questions about what you want to get out of your tool, what you need out of your tool, because then you can start to evaluate based upon the categories that we talked today about what task managers and what applications you’ll actually need. Something to remember when we’re looking at all of this task management advice is that it’s not one fits all. So for me, what I’ve found to be helpful is starting simpler and growing into a system because I’ve realized that building the system is more important than actually using the tool. But if you love using a complex tool and trying to figure that out and building your system into that, that’s totally okay too. This is really only just one approach to handling a task manager. There are many more out there and if you’re interested in sharing a different approach to your tool, I recommend you come over to the Productivity Guild Community at community.effectiveremotework.com and share it in the topic for this episode. There’ll be a link to that topic in the show notes as well and we would love to hear from you.

18:32 Well, that’s all for this time. If you want to join in on the discussion for this episode or you want to connect with others who are in the process of becoming better on their productivity journey, head on over to the Productivity Guild at productivityguild.com. Or if you want to support this podcast and get access to video modules, productivity courses, and more, consider signing up for a Pro membership at the Productivity Guild for just $10 a month. Get a free month trial using code PROCESS19. Lastly, if you like this show, rate us on iTunes or recommend us on Overcast. My name is Justin DiRose and join me next time on Process.


I’m eager to see if Bear has a place in my life. It’s worth a look to see how Justin uses Bear. Is anyone else using Bear? I’d like to see what others are doing with Bear or if they use something else in its place.

When it comes to task managers, I try to find a place for each app. I used Asana as a collaborator tool when I need to work with others. Otherwise, I’m using OmniFocus for most of my personal work.

Whenever I’ve felt my system got too complicated, I would go back to paper and simplify. Then start adding back workflows to get back up to speed. Paper imposes limits which encourages simplicity. I have oftentimes created Frankenstein systems and bolted on many workflows to make my life complicated. Returning back to paper gets me back to the roots of a productivity system.

I also think that we have to avoid the shiny new toy syndrome when another app is released and we flock to the newest darling in the spotlight. I had that same feeling when OmniFocus 3 and Things 3 came out. I had to resist jumping ship when the tool I am currently using still works.

Thanks for reminding us that we are the master of our apps. Don’t let the app become your master. Find a place and purpose for each app and ignore the rest.


I thought I would throw in a different point of view. My research at 2Time Labs shows that the biggest determinant of choice of task manager is task volume.

In other words, when a user reaches the limits of a given task manager, it’s time to consider making a switch. Given that a switch is complex and involves new habits, practices a new app and maybe even a new device, there’s a strong argument to be made for making the most of what you are using right now before making a change.

What makes the choice difficult is that it’s quite possible for a 10 year old (i.e. novice) to experience the same unwanted symptoms as a CEO of a Fortune 50 company. However, as my article shows, that’s just an indication that it’s time to make a change.

The Evergreen Guide to Choosing Your Next Task Management App


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@Fwade - Thanks for the thoughtful article about choosing a suitable task management app. I’ve had the belief of building up slowly and letting my situation change. I don’t like changing task managers abruptly/frequently as it appears to be the case from what I have seen on Twitter. But then again Twitter is a poor barometer of the topic we are talking about here.

I’ve thought of building a system that works on paper first and then choosing a task manager.If a system can work on paper then it is easier to try different task managers.

As we encounter more demanding situations, switch to a more complex app when needed. But don’t switch back and forth like a madman. I’ve read about how some people try to maintain two task managers running side by side as an exercise in sanity control.

Thankfully, I’ve been able to stay in my task manager of choice and work with a BuJo to get what I want/need.

Again, great article!

That’s an interesting approach (building up from paper) but there’s a catch. Scalability is a huge issue in task management and what won’t work on paper may work with the right automation.

But your intent is clear: to figure out the core practices that work in a simple environment, then scale up carefully, probably via different micro-experiments. That always works if you maintain the rigor.

But how about starting with your current habits, practices, apps and devices and have that be your baseline? Then, make the steady improvements using the method you describe?

Most folks struggle to figure out how to do such experiments so they bounce around from one app to another in a random manner. While their search is understandable, without a working theory they end up looking at attributes like how pretty the GUI is and using that as their main priority.

As I mentioned in the article, I jumped around myself (just like you said) when I didn’t have a clue as to the critical importance of task volume.


I myself am also trying to use more paper, but find a way to incorporate the task manager for recurring tasks and long term planning. I still haven’t found the perfect build yet.

My day job I track all on paper what needs to get done. I work in a science field so it’s easiest to do it this way and better traceability.

Personal though would probably be digital task manager, but I hate being on my phone and inputing tasks is a pain. I’m trying Evernote as a daily log/task list of major tasks to do, but as I stated if I avoid my phone then I lose access to that running log.

I think field notes is the way to go for me for that running log and a simple task manager for repeating and long term tasks is where I would end up based on my situation and needs.


Hmmm… I’ll definitely think about this. I found out that I tried to start off with OmniFocus and didn’t really have any habits or practices to start with. I do worry about starting off with the wrong foundation. But that’s the beauty of experimenting. Over time, I had to figure out that using too many tags didn’t work for me. Hyperscheduling was a fun experiment but eventually died after a month. The idea of using energy levels as a label also was a cringe-worthy experiment that didn’t take flight for me. Instead, I had to learn about reading my peak times and my low energy times throughout the day and working on certain types of tasks during those high and low energy periods were more helpful for me.

It’s been crazy but I do agree with your statement: use your current habits as the baseline and then make steady improvements (or adjustments) the current habits. Thanks for your thoughtful insights!


An interesting post at the MacPowerUsers forum about Systems vs Apps.

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That’s a really good conversation.

Something interesting I’ve learned recently: when you have a system you want to use, it can be really hard to pick a tool.

I think @mercmaj’s thought here is also relevant:

It’s important to invest in our systems versus just the tools. The system is what helps you stay on track; the tool is merely part of the system. If you keep changing tools, it’s like continually changing out the transmission or engine in your car – it’s just going to be messy.

Sometimes we need to embrace the constraints of our tools instead of trying to find a better app. Embracing constraint can make us more creative in finding a solution anyway.

Ultimately, the struggle is not making our system any more complex than it needs to be. Worrying about tooling only causes us to procrastinate and create unneeded complexity in the system.

It’s why I’m experimenting with reverting back to the Bullet Journal – it’s a whole lot easier to keep simple!