February 28, 2025

I Want My DayOne AI

I’d love for DayOne to offer some AI/LLM functionality. I can imagine all the privacy concerns, but in all honestly, this is a case in which because we can, outweighs should-we?.

The simplest use-case is similar to the recently released Readwise Chat — in which you can chat/search with your highlights. For me, this would be less cringe-worthy that reading some of my entries1.

Other use-case is journaling itself. I can see the benefits of a conversation with my journal at both ends of my journaling modes: when I have nothing to say, and when I’m overloaded with thoughts.

The empty page day scenario is easy, this will give templates a whole new dimension. How are you feeling?, did someone say something to make you laugh today? Did you feel you made progress on a project?”. Replace the generics (someone, project, etc.), and now you move from an ELIZA type conversation, to one when LLMs aware of your Journal can really shine: did Bettina say something to make you laugh today? Did you feel you made progress on the Vendor Onboarding project?”. Have the agent then turn the conversation into a Journal entry, and ta-da!.

At the other end of the spectrum, the I’m-all-over-the-place entry will also benefit. It doesn’t seem hard for a model to be able to steer you towards healthy tracks: what are you grateful for? How did that make you feel? etc.

Sprinkle all this with the benefits of conversational data input, with some sort of personality, and all the privacy concerns seem a valid trade-off for me.

There are already some Apps that are doing this. My hope is that DayOne is looking at the most private way possible to deliver on this. Maybe using some Open Source AI/LLM they can host themselves and be sure doesn’t leak out data. Or a client-based solution in which the model is local, and there are no concerns2.

Let’s hope it’s in the near future.


  1. Of which I have a streak of 2453 days.↩︎

  2. Better, but much harder solution.↩︎