I Didn't Need a Task App. I Needed a Coach.

After four rounds of self-hosting, I turned the same idea to another tool: the task app. I have to admit a blind spot here. I kept trying different apps, hoping to find a “better” one. In truth, a tool just needs to fit your needs. There is no perfect choice. I had “wasted” a fair amount of time on this search, and AI kept getting more useful. So I thought of using AI to build a task app that fits my own needs.

What I have used…

I have used quite a few tools: Asana, Todoist, Upbase, Amplenote, Taskade, SkedPal (and quite a few others…). Each one had its strengths. But I never settled on any of them. Either it still fell short of my ideal task app, or the features I needed sat behind a subscription. The fees were not high, but I never felt satisfied enough to pay with peace of mind.

Asana and Todoist were the ones I used longest, about five years and two years respectively. Their free features already covered most of what I needed: Kanban, categories and tags, sync with Google Calendar. But the free versions did not have full time-blocking, so I kept trying other task apps.

SkedPal was the one I came closest to paying for. It records tasks as notes, which matches my note-taking habits in Obsidian and Evernote. Its time-blocks are clear and well organised: you can set blocks that open on different days or at different times. Its most powerful feature is auto-scheduling. It updates your schedule dynamically, based on your presets. For example, you have a few tasks in today’s time-blocks. You work very efficiently, and by noon you have finished the whole day’s tasks. You tick them off and think, “I’ve finished today’s work, I can relax a bit.” But the clever app sees that the afternoon is now “free”, and it fills it with other unfinished tasks to raise your productivity. How clever SkedPal is, helping its users make full use of their time!

The app has many settings to decide in advance how time-blocks get updated or arranged, and how tasks are prioritised. Even so, this clever scheduling hurt my morale. Being more efficient only earned me more work. And setting it to hold off on new tasks felt a bit lazy. Beyond the hit to morale, setting up and updating these presets also took a lot of mental energy. So when the trial ended, I did not carry on.

What I need is…

After trying different apps, my favourite workflow is this: write a project outline in my notes, set milestones, then break them into tasks of about 30 minutes. To arrange the tasks, I sort them on a kanban board and do them in time-blocks on a calendar. I once tried to build this workflow in Obsidian, but problems along the way forced me back to task apps. Through 2025 and 2026, Upbase and Amplenote mostly met my needs.

With the AI wave, my workflow started to feel a bit inefficient. So I thought: why not use AI to update my workflow and replace the task app? I would only need to write down ideas and goals. AI would break them down, tag them and arrange my task list for me. I would no longer set up, tag and split tasks by hand. AI would reorder them by each goal’s deadline and progress. I would no longer keep sorting and arranging tasks one by one. AI would help me find the tasks that fit today or this period. And I would not need to dig out the tasks that had fallen behind. AI would remind me to catch up and show me where to improve.

Text files and AI

Like the other posts in this series, this task system was built with AI’s help.

My setup:

• Text files: one active task file (active.md) as the live task list, and one text file for each goal or area of work, with the goal and its main task list.
• Sync: a private GitHub repository as the bridge for sync and backup. My aim is still to keep the text files stored locally, but GitHub makes the setup on mobile devices simpler.
• AI setup: on my computer, AI can read and edit the text files. In a conversation, I set up a prompt with the AI, so all later task planning has something to run on. To change it, I just tell the AI in a conversation or edit the prompt. New features can be added any time.
• Daily routine: every evening I tell the AI which time-blocks I have free tomorrow, and it finds the tasks to work on. Every week I talk with the AI to update progress and adjust my goals.

What I gained after one month

I have only used this AI task tool for about a month, and my daily workflow is already more efficient than before. My mental energy no longer goes into adapting to a task app’s workflow or settings, or into tagging tasks and editing lists. I can focus on the goals and on doing the work. And the AI is like a coach or a companion pushing me towards my goals, not like a task app that buries me in task lists.

This is part 5 of the Self-hosting series. So far it has covered text, attachments and images, the blog, a local AI platform, and my daily task list. That is already further than I planned at the start. At first I only wanted to deal with one to-do item that had been open for years. Now my self-hosted system covers most areas of my life. So the series will pause here for now, until the next problem comes along.