Searching For The Perfect To-Do List App

My excruciating quest for the ultimate procrastination tool

Nico Glennon
Oct 7, 2017 · 13 min read
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Productivity makes me anxious.

People who share my obsession with to-do lists likely also share my ‘productivity anxiety’, the constant feeling that I’m not maximizing the utility of my time. They might also share the ironic understanding that making lots of to-do lists is just high-level procrastination — although it feels like you’re getting a lot done when you’re slicing your day into nice little one-hour tasks, the reality is that nothing has yet happened and you’re still at square one.

Nonetheless, writing a to-do list can actually generate enough momentum to get you started with your daily tasks. The whole process then ends up being a net plus for many of us. Because of this, the ritual of making a list is very important — in fact, it is so important to us that it fuels a whole industry profiting off this compulsion.

I’ve spent the last two months looking for a software developer position in Chicago after attending a bootcamp. I have never been unemployed before, and coming from a job where I had to meticulously plan my entire day before I even got to the office in order to not lose hundreds of thousands of dollars for the firm, the new lack of structure was an incredibly difficult transition. My productivity anxiety was crushing me. List-making was at an all-time high, while productivity was at an all-time low.

Without really noticing, I had always used a few combination of to-do list apps to keep track of different things: I used Microsoft OneNote and Calendar for my job tasks, Google Keep for my grocery/shopping lists, Evernote for my long-form writing & business ideas, and both my iPhone’s Reminders and Notes app for general daily tasks. But once my job search began and I started to rely heavily on my organizational skills to fuel my productivity, I realized that I had a lot of information spread out across several platforms and it was exhausting and time-consuming to keep track of where everything was.

I then began my search for the one to-do list app that would organize my entire life and help me get the developer job I wanted — one list to rule them all. No more migrating all my notes from one app to another every other week. No more having four different to-do lists open at the same time, all with the same tasks worded slightly different. No more anxiety from wasting time and energy juggling different tags, projects and keyboard shortcuts. I inadvertently set out on one of the most blatantly unproductive spirals of my life — a quest for the ultimate procrastination tool.

Here’s what I found. But before we start, a few things:

  1. The products are listed in the order that I used them. So first or last doesn’t necessarily mean best or worst.
  2. I’m only writing about the products that I didn’t delete two seconds after downloading/opening. That is, all of these apps captured my interest for long enough that I used them pretty extensively.
  3. I only considered free or almost-free options ($3/month subscription was pushing it). If I wanted to pay a lot of money for my vice, I’d pick up smoking.
  4. Some things I complain about will seem minuscule and insignificant, and you’ll think I’m insane for obsessing over such trivial details. I apologize in advance for that.

Alright, let’s get on with it.

1. Evernote

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Evernote web was always doing too much.

Evernote felt like an absolute overkill for my general use, which was mostly to-do lists, tasks and ideas. I kept having trouble navigating the unlabeled vertical sidebar to first find the right Notebook, then its sub-Notebook, then finally find my Note. There was no default landing page setting where I could choose to first arrive on today’s tasks — instead the app took me to the last note I had made, and as an alternative provided a ‘shortcuts’ icon where I could place links to important notes. Still, I was three clicks away from what I wanted to see at first glance.

When editing any note, the array of tools and integrations that appeared above it made me feel like I was working on a Word document, which was pretty daunting. I didn’t need to import Google Drive videos or share my weekend tasks on LinkedIn.

In general, Evernote had been absolutely great for certain things like taking notes in class, but I was looking for something simpler, less convoluted, and with a focus on productivity.

2. Google Keep

Keeping colored cards for reference to different projects was genuinely fun — setting reminders for myself was easy and quick. Everything was so visually appealing. I invited my girlfriend to sign up for Keep and then shared access to my ‘grocery’ and ‘home’ lists so we could keep track of household things together. Where had this been all my life?

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Google Keep ended up making me feel messy inside.

Then things got crazy. Because of how easy it was to turn anything you saw online into a note (Chrome plugin FTW), after a few weeks of throwing in random stuff here and there my landing page started to look like a messy desk. Things required a lot of scrolling to find, and it made me queasy not to see my information concisely all on the same page. That feeling of messiness was the exact opposite of what I was looking for in a task manager and life organizer.

Perhaps if you work well with a dash of chaos in your daily routine, or can sleep at night knowing things are not perfectly aligned at 90-degree angles with one another, Keep might just be for you. Unfortunately, although I loved Keep in theory, it did not work out for me in practice.

3. Apple Notes

Of course, I immediately took this casual comment as gospel.

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Apple Notes: you already know the drill.

It didn’t take long to figure out Notes would not work for me. First, the ‘Folders’ section felt very crowded on my phone — The whole iCloud vs. On My iPhone always confused me when I opened it up. I knew I could only use the iCloud folders (to sync everything with my laptop) so the other stuff just felt like a distraction. I was trying really hard to live by Baiju’s words: Simple, gets the job done —but the app wasn’t helping.

Once I updated to iOS 11 on my phone, a small little thing started bothering me. Opening up a note felt like it took just a little longer than it should. I couldn’t remember if this was the case before the update… but it was noticeable every time I tapped on one of my lists. After a while it started driving me crazy. (This is the kind of stuff I apologized for in advance).

What I disliked the most was that I couldn’t pin one of my lists to the top of the notes, and thus was always three clicks away from my desired landing page every time I opened up the app. This got old after a while and I decided to see if there was something else out there. Sorry, Baiju!

5. Bear

That aspect was not weird to me given I was familiar with markdown, but I can imagine many people wondering what is the floating ‘H1’ next to their title that they cannot hide or erase. Also strange for them would be the use italics or bold in their notes: it will look like *this* or **this**, respectively. No getting rid of the asterisks. Maybe Bear was not built to be a task manager, but I was on a mission to make it one.

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The Bear desktop app was polished AF.

Bear also uses a very cool, very tongue-in-cheek feature called linked lists. You can link one note to another via hyperlinks internal to the app. That way you can toggle back and forth between lists by clicking on something you’ve highlighted and linked, which for me was super useful for connecting the “Today” list with, say, my general “To-dos”. I could quickly cycle between them and allocate tasks into the time slots I had available that day.

I migrated all my stuff to Bear when I found it and happily signed up for their $2/mo plan (that’s right, Bear is not free… but it was really, really pretty!).

A few days after, I started to notice the linked lists feature would sometimes glitch and either not take me anywhere, or take me to the next note but show me the contents of the previous one. I was also frustrated with the small number of theme options — although the actual app icon changes color to match your selected theme (which is insanely cool), about half of the themes used a seemingly random combination of clashing colors. For an app seemingly so rooted in art design, this made no sense to me.

I saw a huge benefit in keeping snippets of code in my notes (Bear supports syntax highlighting for all popular programming languages). But when I pasted in or typed certain Ruby classes for which the line of code ran longer than the width of the app, Bear wouldn’t indent the code correctly nor let me manually correct it. It was a weird bug that I could not solve, and one that finally convinced me it might be time to look for an alternative.

I fell out of love with Bear a day before the end of the free trial and cancelled my subscription just in time. I’ll definitely keep an eye on the product as it evolves, and still might return to it if some of these things change.

6. Microsoft To-Do

I hesitated once I opened the web version of the app, though. It looked like a basic list app, the same magic from the mobile app simply not there.

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To-Do’s ‘My Day’ list will recommend tasks if you click the top right light bulb.

What makes To-Do stand out is its suggestions engine. Microsoft is a big believer in productivity through AI as Bill Gates has stated himself many times in interviews. In To-Do, you get a slightly different experience that in all other list apps — every day, a “My Day” smart list would recommend tasks for you to do today from stuff in other lists. It’s a very cool experience and really makes you feel like all your different lists of responsibilities are connected and served to you. It was not a simple blank canvas where you’re just writing things down, but instead a sentient assistant helping you become a better you.

I switched to it for a few days because I loved the really well-designed iPhone app. But the web app for my laptop was not as engaging, and it was what I was using the most. There was nothing about the design of the web app that made it better overall than other things I had already tried. Microsoft had not developed a desktop app for Mac, either, which meant having to have a tab open in my browser for it constantly.

Finally, the ‘My Day’ smart list would sometimes recommend things I had written down that didn’t make sense to do in a single day, such as software or business ideas. There was no way for me to separate the things that were ok to feed to the AI for later and those that weren’t. After long consideration, I decided to pass on it and continue my search.

7. Simplenote

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Simplenote’s UI. Minimalism meets emojis.

Simplenote has the same basic functionality as Evernote — nested notes under a common thread. In Simplenote, notes group together under Tags. Tags are easy to place and remove, and notes can be under multiple tags. Simplenote basically felt like Evernote with all the unnecessary stuff removed, on a completely minimalist interface. I could even pin my ‘Today’ note to the top, too!

I ended up adding a personal touch to it by placing an emoji in front of each note’s name: for example, my ‘Today’ note is styled ‘☀️Today’, which provided a bit more life and color than just black words on a white background. This balance between a flicker of fun and the simplicity of a bare-bones text editor (no bold or italics, just title and body) really clicked for me.

Although it didn’t have reminders, alerts, integrations, or any functionality besides a super-basic text editor, I decided Simplenote was it. It was not perfect by any means, but it felt like best option for what I needed. After being pulled in so many directions struggling to utilize features of so many different platforms, the completely blank slate of Simplenote was a breath of fresh air.

8. Todoist

First of all, Todoist is absolutely beautiful to look at. The minimalist framework puts the focus on your tasks and projects, whether they are overdue or not, and keeps things clean and uncluttered. Everything is pixel-perfect and the color use is subtle but tasteful.

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Todoist was clearly built with productivity in mind.

My absolute favorite thing about Todoist is how easy it is to set a task’s due date — if you create a new task called ‘Read New Yorker today 4:00pm’, Todoist will parse your task using natural language processing and save it as simply ‘Read New Yorker’, with a due date of today’s date at 4:00pm. It will pick up pretty much anything, too: I’ve been writing things like ‘tom 9a’ and it knows I mean tomorrow at 9:00am. You can also set a task’s priority level by typing ‘p1’, ‘p2’ or ‘p3’. All of this is super useful for someone like me who doesn’t like to lift their fingers off the keyboard to use the trackpad unless absolutely necessary.

After a week of using Todoist, I ended up syncing it with my Calendar. Everything I scheduled on Todoist would populate automatically and gave me a really nice visual representation of my day/week, the best way to plan out my time yet. This is what that final setup looks like:

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The final setup on my laptop: Todoist + Calendar.

Everything about Todoist inspired productivity: a minimalist layout with zero distractions, amazing way to quickly jot down your tasks and their due dates, even a Karma feature that keeps track of how many tasks you’ve been knocking down and congratulate you when you’re on a roll.


Needless to say, this whole article is my unique personal opinion and is quite subjective, as you might’ve noticed. If you have other productivity apps you think I should check out (although I probably already have), feel free to leave a comment or message me!

***UPDATE — 1/13/18***


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A few months after publishing this story I discovered Notion and I made the very difficult choice to cancel my Todoist subscription. Do yourself an enormous favor and check it out: the marriage of functionality and product design in Notion is unparalleled with any of the other products in this space. Huge shoutout to the Notion team, you crazy for this one!

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Nico Glennon

Written by

Human in the simulation.

A network of business & tech podcasts designed to accelerate learning. Selected as “Best of 2018” by Apple.

Nico Glennon

Written by

Human in the simulation.

A network of business & tech podcasts designed to accelerate learning. Selected as “Best of 2018” by Apple.

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