The todo apps I deleted before I built Ikoi

The last app I deleted was Sunsama. I’d been paying $20/month for nine months. The deletion happened on a Tuesday afternoon between meetings, and the trigger was specific: I opened the app to plan tomorrow, watched the daily-planning ritual flow load, and felt the dread of a tool that had become another task.

That’s the pattern. The app meant to reduce overhead had become overhead.

Here are the four apps before Sunsama, in order, with the specific moment each one stopped working.

Things 3 (deleted: 2021)

The most beautifully designed productivity app I’ve used. I bought it on Mac and iOS, and used it for about fourteen months. The interface felt good in a way no other app has. The animations were honest. Cultured Code clearly cared.

Failure mode: the app rewarded careful organization, and my organization stopped being careful around month nine. The Areas/Projects/Headings hierarchy required me to maintain a system I no longer had energy to maintain. When I stopped maintaining it, the app showed me my own neglect. Beautifully.

I deleted it the day I realized I had a “Today” view with 23 items, none of which I’d actually done, and a “Someday” project with 147 items I’d never look at again. The app couldn’t tell the difference between “this is on hold for a real reason” and “this is dying.” I could.

Todoist (deleted: 2022)

I came to Todoist for the natural-language input. I stayed for the cross-device sync. I left because of the gamification.

Karma points. Streaks. Productivity trends. All of it engineered to make me feel good when I completed tasks. None of it engineered to handle the days I couldn’t.

The breaking point was a specific notification: “You’re 1 day away from breaking your 47-day productivity streak!” I had not been productive for 47 days. I had been checking off the easy items every day to maintain the streak for 47 days. The hard tasks were untouched. The number was a lie I was telling myself, and the app was paying me karma to keep telling it.

I deleted Todoist that afternoon.

TickTick (deleted: 2022)

I tried TickTick for about three weeks. It does a lot of things. That was the problem.

The default surface was a cluttered list. The Pomodoro timer was buried. The habit tracker was buried. The Eisenhower matrix was buried. Every feature was good in isolation, but I had to remember which one to use, when, and where to find it. The cognitive overhead of operating the app exceeded any productivity benefit it might have offered.

The deletion was not dramatic. I just stopped opening it. After three weeks of not opening it, I uninstalled.

Structured (deleted: 2023)

Structured is a beautiful concept. One scrollable timeline that combines tasks, calendar events, and reminders into a single visual day. For people whose problem is time blindness, this should be perfect. It’s the closest any app I’ve used has come to solving that one specific problem. (I wrote about the Ikoi-side answer to time blindness separately.)

The reason I deleted it: the timeline was honest about how full the day was, and being honest about how full the day was made me anxious. There’s no hide-the-overflow option, and there shouldn’t be. The whole point is honesty about time. But on the days I had time anxiety, the app made it worse, not better. And those were exactly the days I needed help most.

Structured optimized for a fully-functioning user looking at a manageable day. I am sometimes that user. I am also sometimes the other user.

Sunsama (deleted: 2024)

The daily planning ritual is a real innovation. Sit down each morning. Pick today’s tasks. Estimate time for each. Roll over what you didn’t get to. Do it again tomorrow.

This works beautifully when you have the energy to do it. When you don’t, the ritual becomes the task you’re avoiding. The app waits, patient and judgmental, until you sit down and tell it about your day.

I tried for nine months to build a “5 minutes of Sunsama every morning” habit. I succeeded for stretches of about two weeks at a time. Then I’d miss a day, then three, then a week. Each return required catching up on the days I’d missed, which meant the daily planning ritual became a backlog of skipped daily planning rituals. Recursive failure.

I deleted it on the Tuesday I described at the top.

The pattern

Five apps, five different mechanisms, one shared architectural assumption: the app works best when the user is at their most functional. Things 3 demands maintenance. Todoist rewards consistency. TickTick assumes attention. Structured assumes equanimity. Sunsama assumes daily presence.

Every one of these assumptions is fine for the median user. None of them survive contact with an ADHD brain on a bad day, and bad days are precisely when the user most needs the app to work.

I built Ikoi because, after deleting five apps, the next move was either to accept that no app would work, or to try building one with the opposite assumption baked in: the app should work best when the user is at their worst. Whether I’ve succeeded is a different question. The premise is at least mine.

The app on my phone now is the sixth one. I haven’t deleted it.

Related reading: The 2-minute door opener on one specific design choice that follows from this premise, and ‘Not today’ is a feature on the language side.