Posts about Todo Apps

A couple years ago, somebody recommended Carl Pullein’s YouTube channel on the Mac Power Users forum.

This really messed me up.

The video that caught my eye was called ​“Stop Using Your Task Manager as a Project Manager,” and it sort of blew my mind. I have been a devout Omnifocus user for fifteen years or so, with brief flirtations with Things and Todoist, and have always stored my tasks there.

Carl’s thesis is that Omnifocus, Things, Todoist, whatever — these are not project managers. The tasks might be linked to projects, but you’re not dealing with the project in those apps. You’re working with the tasks. Carl’s problem is that, when you check off a task in those apps, they disappear from view. And if it’s going to be a project manager, you need a bird’s eye view of things.

This has sent me down a years-long rabbit hole. While Carl espouses Gantt charts, I hate them. I’m sure they’re useful, but I have a job, you know? Carl also espouses spreadsheets, but my friends, I am allergic to spreadsheets. Extremely allergic.

I am a designer by trade. I might sound superficial, but if I’m going to use a tool, it’s got to be aesthetically pleasing. Gantt charts and spreadsheets are not going to cut it.

So I’ve tried Asana, ClickUp, Notion, and several others that I genuinely don’t remember anymore because the dalliances were always brief. Asana got kicked out for being too expensive for a single person. ClickUp is a disaster; it’s so broken that should be punishable by law.

And Notion is… well, it’s Notion. Do you like proselytizing the software you use and spending all your time click-click-clicking around instead of getting something done? Notion is for you. Do you like software that looks like junk, but is extremely customizable? Notion is for you. 

I have spent years on this, and still don’t have a great project management solution. At this point, given the way that LLMs are doing, I’m considering writing everything in Markdown docs (I love Markdown and have used plain text for all my notes since 2010).

I have a few needs:

1. First, I am a single individual. Sometimes, I need to share tasks. For example, my wife is on maternity leave for the next eleven months, and she wants to help with my business’s finances. (She never really sees the money going in or out of the business, I think she’s always wanted to, and it takes two hours a month — so she has the time.) I need to share my monthly project with her so she knows what receipts she needs to grab. So sharing needs to be possible.
2. I take a lot of meeting notes.
3. I write a lot of notes while working on a project, and trying to reason something out.
4. I also collect all the files clients send me.

Outside of tasks, everything else is basically a simple file, or a collection of files. So I think what I’m going to do going forward is pretty simple:

1. I need to use a task manager that supports sharing projects. In my case, since the only person I really need to share tasks with is my spouse, I could use Things or Omnifocus and give her my login credentials. Then let sync just deal with the rest. (Otherwise, the ​“best” option for my tastes might be something like Todoist.)
2. Each client should get one meeting note. For the past two or three years, each meeting note has been its own log in Notion. I have never reviewed those files, or at least very rarely. Clients often have multiple projects, but those projects might weave together (like a book design and an accompanying website, for example). I’ve been using databases to connect everything in Notion, but this seems like tremendous overkill for one person. It’s so much slower than just typing in plain text on my Mac.
3. For the notes while I’m working on a project, I should make each note a date-based plain-text note and stick it in a project. Maybe I should just make this one file too, which H2s for different dates? Some of these notes run pretty long; much like this post, I ramble about things that would be of interest to only me.
4. Those files that clients send me already go into the appropriate project directories in my Mac, in a subdirectory called 01 Assets (numbered so I can sort them in the Finder alphanumerically).

This would mean that everything that touches a file is a file inside a file system, and todo lists are the only things that aren’t done in plain text. If a project ever needs a top-level file describing it, that’s a non-issue in this system too.

I think this would cover it. A standard project directory would look like this:

Client Name:
- Client Name Meeting Notes.txt
- Project Name
	01 Assets
	02 Editable Files
	03 Review 
	04 Delivery
	Project Name.txt
	Project Name Notes.txt (or a subfolder)

Then tasks can live wherever they need to live.

If you’re reading this and you have any other options you might recommend for something like this, let me know! I’ve never worked in a team in an office setting (always freelanced and ran a studio), and this is one of my blind spots.

For years, I’ve gone back and forth from OmniFocus to other task management systems. I’ve tried so many of them: Things, Todoist, Wunderlist, Basecamp, Reminders, Asana, 2do — I’m sure I’m forgetting a few. I’ve never lasted more than a month or two with any of these before coming back to OmniFocus.

I have a love/​hate relationship with OmniFocus. (I once called OmniFocus ​“expensive” and ​“dystopian” on my personal blog, which may have been a bit melodramatic.)

But this app is honestly the only task management system that lets me work the way my brain works.

I’ve spent the past year going back and forth between all these systems, and after purchasing it three or four years ago (whenever version 2 came out), I’ve come full circle to embracing OmniFocus again. I’ve made a lot of notes over the past year about how I work and why OmniFocus works for me.

If you’ve been struggling to embrace a digital task management system, or trying to figure out what app you should use, then I hope this can help you.

Outlines of tasks

First of all: like many creative types /​coders that I know, I tend to think in outlines. Give me the back of a napkin and I’m writing a list out on it. OmniFocus is the only todo app that feels like an outlining app. (Obviously, that’s because OmniFocus shares heritage with OmniOutliner — another app I’m a huge fan of.) So every day, when I’m doing a bit of a brain or idea dump, I can write it exactly how I would an outline. (It’s even better once you have the keyboard shortcuts memorized.)

But I know I’m not using OmniFocus right. I don’t use Reviews (well, not often). I don’t know use Contexts at all (seriously, not even a little). But I use Projects religiously. I’ve organized my life into folders of projects in OmniFocus. Each folder includes a project called Miscellaneous, which I use to dump individual tasks that don’t belong to a larger project, but still need to be filed in the right place. I have a folder for my studio, a folder for my church volunteering projects, and a folder for each client and product that I cater to. When a task gets added, assuming there’s a project or client related to it, the task immediately gets dumped in the proper spot.

I know what you’re thinking: ​“This sounds like a ton of work. I don’t want to think this hard.”

But it’s really not. It works just like an outline. Here’s a bullet list to show off (in brief) what a typical list within folders might look like.

• My Studio Projects
  • Website Update
    • Write New Copy
    • Get a Headshot
• Acme Corporation Projects
  • Brand Package
    • Create logo
    • Design system
    • Put system into a beautiful book
    • Collaborate with an awesome A+ printer to get the book printed
  • Website Update (Project Two)
    • Design
    • Development
    • Kick-Butt Copywriting

Etc, etc.

It’s not hard. It’s sensible — the exact same way you’d write it down on the back of the napkin.

Deferred projects

To manage the bloat of projects, I also set up a ton of deferred start dates, which often repeat annually for clients on retainers. I can plan out a client’s entire year with them, and then start nudging them the day a project is set to start. This has the side benefit of hiding any ​“inactive” project from my regular OmniFocus views. So there’s not too much clutter. Just enough to get a birds’ eye view.

Managing it all with perspectives

All of this sounds really hard to manage, I know. I’ve got about 50 active projects going on at any given time.

This is where a task management system usually falls apart: what happens when you have hundreds and hundreds of items in it?

Most people start using Contexts at this point. I really don’t understand Contexts. I don’t get tags either. These systems don’t work the way my brain works. They give me headaches.

How I work with all this

I bought the Pro edition of OmniFocus, so I could set up custom perspectives. Perspectives are, for me, a bit of a lifesaver. They let me focus on individual projects at a time, instead of the full monte. (Hence the ​“Focus” in OmniFocus.)

I have two perspectives I use religiously.

One is called ​“Doing”. I manually select the projects that I must make progress on every day right now, and have only those listed in this perspective. With one click, I can go to the perspective, see a quick list of the projects I should focus on, and check on the related tasks for each project.

The other perspective is called ​“Today”. It also focused on a project, but this project is just a single action list called ​“Today”. Every morning, I delete everything in the list and write out only what needs to be accomplished that day. I don’t assign a due date or anything — I only use due dates if my life depends on it — but I start working through ​“Today” every time I finish in my Forecast.

My key Principle: Daily task curation

Most hardcore OmniFocus people have a Today view in OmniFocus. The problem is, that Today view is usually based on some mixture of defer dates, due dates, and flagged tasks. I can’t have an entirely automated system like that; I need to manually curate my daily tasks.

I’ve tried, and tried, and tried to set up so many similar lists in any other app, but it never works for me. OmniFocus is the only app that bends to my will. (Things comes close, but their app is too inflexible to be of any real use for people with a million projects and areas of responsibilities.)

This workflow works if you’re the sort of person that dumps everything you need to do into your phone, but still writes out a quick list on paper every morning. I’ve just elected to make the whole thing digital.

If I’m being completely honest: you could probably make a compromised version of this system on anybody’s platform. But I don’t think anybody else makes it as easy to do what you want.

This isn’t a sales pitch. I get 0% of the money from doing this. I’m just finally happy with my system. If you want to try it out, you can check out OmniFocus on OmniGroup’s website.

Most digital todo lists suck. I’m sure you’re aware of this. I’m certain you’ve probably spent hours combing through tips on LifeHacker about how to organize the chaos of your life with ​“this one simple app that will blow your mind.” Or maybe you’re like me and you’ve bent over backwards to fit your workflow into somebody else’s expensive dystopian view of getting things done.

I don’t need to tell you that task management apps suck. 

But I need to share this because nobody is saying it, and we’re all pretending like we’re organized, but the truth of the matter is that the people who make these apps must have nothing to do — because their apps don’t work for busy people. So this post is for them. 

I only need one thing from a todo list: to tell me what I should be working on right now. And when I’m done that, what’s the next thing I can do?

That’s it. No gimmicks. It’s that simple.

Yes, all your extra features, like sub-tasks of a sub-project inside a project within an area of responsibility in the context of ​‘Phone Calls’ are all well and good, but if you cannot give me a high-level look at what needs working on today, don’t bother.¹

This isn’t just about what’s due: it’s about what’s important, what’s in progress and what big-picture project I should be working on. If I need to finish a project by Friday and it will take three days, then it should show up in a special Today view as early as Wednesday and not leave the Today view until it’s done, even if it’s overdue by three months and a day. 

My task management app should be about managing what’s important, making changes to the unimportant on the fly, and getting crap done. 

For reference, this is where I’m storing all the crap I need to do now. 

Note: This post was originally called ​‘I Tried Every Todo List App So You Don’t Have To’. I changed it for the sake of brevity, not because it’s untrue. I think I did try almost every todo app on the market for iOS and the web.