I didn't plan to let an AI manage my to-do list

Eddie (my AI agent) now manages my to-do list.¹ I hadn’t planned that. It kind of happened on its own. As I wrote in one of my previous posts, I like interacting with him via Telegram. The playful UI just has something to it. But it also has downsides. For example, it can’t render Markdown tables, and it breaks up messages exceeding a certain length. That means when Eddie creates longer research reports like stock analyses, vacation plans or whatever, they don’t look nice. As a result, Eddie saves them on the filesystem and I grab them later.

But grabbing becomes a bit annoying with my security precautions. I run Eddie in his own network to cut him off from my other devices. That network also doesn’t allow SSH connections between devices. Meaning I can’t simply SSH to Eddie and copy them. Instead, I connect my laptop via an Ethernet cable to get access. I still like this setup since I consider it rather safe, but I wouldn’t want to do it all the time.

I thought about using GitHub, which renders Markdown perfectly. I’d only need an access token for Eddie and a repository he could write to. Then I could read what he created in the GitHub app on my phone. Technically not the worst solution, but it somehow makes me nervous. What if, in a moment of carelessness, I check out the repository on my computer? What if Eddie gets compromised and uploads malicious files to it? Maybe that sounds paranoid, but when I chatted with Eddie initially, he recommended something else that caught my attention: Obsidian.

I maintain a healthy on-off relationship with Obsidian. I kept coming back to it, but for the longest time now I’ve simply used Apple Notes. I don’t need a lot of fancy features or a second brain, just something to take notes. I’d never give Eddie access to my iCloud, but I liked the idea of trying out Obsidian for this. Unfortunately, Obsidian Sync only ships inside the app itself, and Obsidian, a note-taking app with a GUI, requires a display connected to Eddie.

I won’t connect a display to Eddie. I vaguely remembered that I’d read release notes about an Obsidian CLI some time ago, so I tried to push Eddie to search for a solution, but he didn’t come up with one. One quick Google search of my own did. It turned up Obsidian Headless.² They released it only one month ago, and it’s still in open beta. Exactly what I needed.

An npm install later and with $4 less in my bank account (I subscribed to Obsidian Sync) Eddie and I now share an Obsidian vault. As for the security consideration, you can configure sync settings for every Obsidian client. On my phone and laptop, I only sync Markdown files and images. Even if Eddie uploaded anything else, possibly harmful, my clients wouldn’t pull it.³ The same goes for community plugins, which Obsidian doesn’t sync by default. That one matters more than the file types, since plugins run as JavaScript on my machine. A git checkout, by comparison, offers no such filter. It simply puts whatever sits in the repository on my disk.

All right, so now I could read Eddie’s research reports nicely on my phone. But then I noticed something else. The to-do list in my Apple Notes works more like an unorganized inbox for thoughts and notes. It sometimes contains actual to-do items. What if I let Eddie manage that?

Together with Eddie, I first decided on goals for the next six months. I did that so he could track me a bit and make sure I work on my goals, but also so he could rank to-do items against them. I then gave him the items from my Apple Notes to-do list and asked him to build a to-do list in our shared vault, ordered by priority (high, medium, low). We also created another inbox list in the vault, where I just dump some things I should work on. A nice little cron job glues it all together every morning: Eddie goes through the inbox and moves the items into the to-do list, ordered by priority and potentially linked to a goal.

I really like this process, since I can concentrate on checking off items instead of managing them. People joke about Notion users who spend more time setting up their to-do lists than working through them. Not with this setup. It simply feels better to get things done than to sort them. Next I want to integrate Eddie further, into checking off items alongside me, and maybe that turns into a future blog post. Then again, writing this post made me notice something: I’m now getting managed by my AI agent.