The Problem with Task and Project Management

I’ve never had a task or project management system that has felt fully supportive of my life and my work. That doesn’t mean I get nothing done, but it means the path to getting things done doesn’t feel as good as it should.

Broadly, I think the problem is that task and project management is an inherently complex request: “manage all that I must do and want to do in this world and make sure I do it in a sensible order, on time, and that I let no one down”. No pressure. 😅 

I wanted to figure out a system for myself that actually worked, so last month, I started thinking about it more. I came to realise that any time I’ve tried to “create a system that works for me”, I’ve implicitly translated this into “find one app that does it all”. That is not how I work in any other realm, so I’m a bit surprised I’ve never realised I was on a futile mission beforehand. In reality, I just don’t think an out-of-the-box-all-in-one-app could ever do everything I’ve realised I want/need. I want to demonstrate why in this post.

Table of Contents

• What is task and project management?

• What is my problem?

  • routine tasks occur often, but not regularly

  • all tasks have dependencies

  • yes… but not everything is like this

• So what’s my solution

What is task and project management?

I think it’s the what, the why and the how of human activities.

1. what do we need to do?

2. why do we need to do it? (enter contextual factors such as projects, goals etc)

3. when do we need to do it?

4. how will we get it done when it’s time?

We typically think about task and project management as work-adjacent—what do you need to do to get paid? But I don’t love this restriction. I think keeping on top of all the projects you have in your life can be empowering. So that’s some underlying thinking here!

But regardless of how you define task and project management, it’s important to have access to the big picture and the little picture — what’s on your plate generally, versus what are you going to actually do today. These pictures need to talk to each other. I’ve never managed to achieve this in any life phase I’ve had, so it was time to figure out the problem precisely, and fix it!

What is my problem?

At the core, I believe there are two overlooked problems in a lot of apps for my way of viewing tasks and project management.

1. all tasks have some form of dependencies, and a variety of dependency types. Few apps deal with dependencies at all, but it’s the only way tasks make sense to me. I love context. 🥥 

2. tasks often occur in routines and these routines set how we should approach them. Much of my life and work is routine, and I need to work with that and save myself something thinking there.

Then, perhaps the most crucial point of all is that not all tasks fit these two points. Or if they do, perhaps knowing the routine/dependencies is just second nature, therefore employing an app to help deal with it would be overkill. I’m not interested in over-engineering for fun, I’m interested in having a system that does what I want it to!

Let’s discuss these points further.

routine tasks occur often, but not regularly

In my experience, tasks are generally predictable, though not always in terms of a schedule. I believe most of us could break down our lives and job roles into various routines, which I see as sets of tasks that are done together: my filming routine, my payday routine, my social media posting routine etc.

These routines might happen at specific times each week or month, like a weekly review or the preparation for your Monday team meeting. In these cases, recurring tasks (and subtasks) work great here, and many apps deal with this well. However, crucially, not all routines follow this regular cadence. Routines don't necessarily dictate when things need to happen, rather they indicate that certain tasks occur together and often in a set order. This is what is predictable.

For example, I must always film a video before editing it, and I must edit before I upload it. Filming a video always includes these three tasks, but I don’t film every second Tuesday at 11 or every Monday at 3. I just film when I can. So when it’s time to film a video, I have to add all the associated tasks to my task list (and believe me, it’s much more than 3!), and schedule them all. But if it’s routine, I shouldn’t need to do this, precisely because it is predictable.

I decided that in an ideal scenario, when it’s time to film a video, I would like to click a button and see all necessary tasks appear in the correct order, scheduled around my calendar and wider task list. Easy, right? Wrong. Scheduling tasks isn’t that easy, which brings me to my second problem.

all tasks have dependencies

All tasks have a variety of predictable dependencies, yet few task management apps deal with them all that well. Existing options are somewhat limited and clunky, and as far as I can tell, they only consider a dependency as another task. But think about it, dependencies are just contextual factors. Task dependencies are therefore only one group of contextual factors.

Here are some others:

Often, we understand and work with dependencies implicitly. “Do the food shop” is clearly a job for after work, so you can safely ignore that at 11am on a Monday at your 9-5.

This might be why weekly lists work nicely for people as every day you can go and pick from what you want to do based on the dependencies you implicitly understand. But, you still see the task, start thinking about what you should buy to help you use up that broccoli in the fridge, and then you’re off on a tangent and not doing what you intended to do. Perhaps I should switch pronouns here, that’s acutely a me problem, I shouldn’t speak for everyone!

But the point is, we see tasks we know we can’t complete right now all the time. We might be waiting for an email, for the noise outside the window to stop, or to complete a different task first. I don’t want to see such tasks until the necessary context is correct. It would be easier on many levels to “stop thinking and start doing” if my task list was actually relevant to me right now.

I find this even more irritating (therefore I’m more motivated to solve the problem) given so much of my job and my life is routine. I was curious to know if the routine element was just me, but I asked my family and friends who do very different jobs to me, and they all found some truth in this too.

I’ll take a second to make it clear that I’m not complaining about this as if it’s some form of injustice because obviously it’s not. But we can use technology and digital tools to solve our problems, and this one seems worth solving to me! Because if I have a predictable set of tasks, each with predictable dependencies, why do I have to do the thinking to figure out what to do and when? Aren’t predictable activities prime for automation and even AI enhancement?

yes… but not everything is like this

Then we come to the complicated part: not all tasks are part of routines; dependency management is complex and crucially, we know that random tasks can pop up at any time. So our systems have to be agile and suddenly it’s clear that asking for a system that deals with perhaps some complex metadata whilst also being agile and easy to adjust for when things change might be too much to ask.

That was quite a lesson to me! Along the way, I’ve tried the simpler apps, I’ve tried the database-d ones and neither option worked sustainably. It ended up being easier to manage things in my head with the help of a drag and drop tasks to your calendar app (Routine, Akiflow, Sunsama), hoping that if I forgot to do something, someone would email me to remind me. This didn’t make me feel great, but through all my tests I learned a lot.

Mainly, I learned that you can achieve bits of all the things I’ve discussed today in countless apps; there are always workarounds for a part of a puzzle. No wonder people use 100 different apps in the testing phase until they decide one is good enough to stick to for a bit.

But I think crucially, this problem touches on much more than just tasks and is therefore much harder to solve. We get into scheduling, projects, other people, even our physical location. It’s a lot. Expecting an app to solve this out of the box was never a good idea. Writing this post helped solidify that in my brain, and it made me ask if we’re generally asking our apps to do too much out of the box. Article pending.

But again, I’ll reiterate how I am presenting my views of task and project management. There are clearly brains out there who don’t need to think about tasks like I do, and therefore the apps on the market will work brilliantly for them. But my systems are a reflection of me, so I’ve got to build a system that works for me.

So what’s my solution

We’re now approaching the end of July and I started drafting this post in June. I’ve been on a journey to solve this problem based on what I realised above, and honestly it’s been delightfully good fun.

For me, the answer turned out to be an integrated system based on an agile app (Todoist), a structured, customisable, automation-powered app (Fibery) and an integrated calendar app (Amie). I then added some extras to deal with my extra needs, but the base of the task and project management system is Todoist x Fibery x Amie. Amie and Todoist have a native integration, and Fibery has a robust Zapier integration which I’ve become best friends with.

This system works so well I nearly cried the first day it worked, just from pure relief. I had never felt so supported and that is exactly what our systems should be doing in the grand scheme of things: supporting our lives and making us feel good in the process. 🫶 

I plan to write about my setup after another month of testing, but I thought this would be a good post to write first, so you understand why I spent so long thinking about how to solve my problems (no, not when I was supposed to be working!)

I’d love to know what problems you face with task/project management and how you’ve solved them. 🙂 I’ve found the whole process super fascinating so would love to learn from you!