Notes and Reminders: Pragmatic Relationship Journaling
One note per person. One reminder per follow-up. A relationship journaling system built for people who actually want to stick with it.
Carl Assmann
Creator
I’ve always liked the idea of keeping a journal. The romanticized version I had in mind was creating a calm ritual at the same time every day, writing thoughtfully into a paper notebook. But this doesn’t fit into my life. Thoughts come and go. I want the most important and recent things right on top. I want to find things quickly. I need the journal to work with how I actually live, not against it.
The breakthrough came when I stopped asking “how should I journal?” and started asking “why do I want to journal in the first place?”
For me, the answer was simple: I don’t want to forget important things about the people I care about. I want to remember what my friends are going through, what my family is celebrating, what conversations mattered. That’s it.
Once I knew the why, everything else fell into place.
My Journaling Approach
One note per person. One reminder per thing to follow up on. That’s it.
The philosophy is simple: remove every source of pressure. No daily quota. No perfect format. No guilt for gaps. No obligation to capture everything.
When: Reflection happens naturally. While walking. Driving. After my workout. Whenever I have the capacity. Something sticks with me, I write it down. If I forget it, it wasn’t important enough. Instead of writing things down after each conversation, I sleep on it. A little bit of time is a great filter for what’s worth writing down.
The note: One summary per person, then entries in reverse order. Newest first. I add to it whenever something surfaces. The notes grow slowly because they’re built on genuine memory, not obligation. Reading from top to bottom feels like traveling back in time.
The reminder: When someone mentions something I want to circle back on, I create a reminder. Simple and specific. For close friends, sometimes just “Ask about her week.”. Reminders help me stay in touch when life gets busy. When I see a reminder is due, I find a small moment to reach out.
This works for me because I get immediate positive feedback for asking follow-up questions. The low friction and zero pressure keep me going.
The Tools
For years, this lived across two apps. I used iA Writer for the notes (one file per person) and Todoist for the reminders. Both work great, and both are available on my computer and phone, so I can use whatever device is at hand to add entries. This system works.
The Friction
But there is room for improvement. Todoist is where my work tasks live, household stuff, freelance work. My notes app has everything else. When I opened either app to add a journal entry, I’d see all that other noise first. It interrupted my flow.
The friction came in two forms. First, context-switching between separate tools meant I’d often skip journaling entirely. Second, while writing a note about Sarah, I’d think “I should add a reminder to follow up on this” and then have to switch apps again.
Where AI Can Help
Could AI remove this friction? Turn raw thoughts into structured notes and reminders automatically?
Yes, but only if the AI can access both notes and reminders seamlessly. That’s not possible when they live in different apps. A dedicated app could eliminate the distractions, colocate the data, and let AI actually help. That’s why I built Tilly.
With notes and reminders in the same place, AI can do something useful: turn raw thoughts into structured data.
Say I capture this one thought: “I had coffee with Sarah this morning. She’s really excited about her ML project getting approved for production. Her cat Luna is completely recovered from the surgery now. Then I ran into Emma at the coffee shop later. She landed a huge restaurant rebranding client and seems so much happier about her finances.”
AI parses that, creates a note for each person with the relevant details, and surfaces two follow-up reminders: “Ask Sarah how the project is going” and “Check in with Emma about the rebranding launch.” Without this, I’d manually create separate entries. Eliminating that friction is huge.
It feels like talking to my journal. I just capture the moment, and the app handles the structure. The intentional part (deciding what to capture) stays with me. The tedious part (organizing it) is automated.
Why This Works
The system works because it removes friction at every step.
A dedicated app means I’m never distracted by unrelated tasks or notifications. AI handles the busy work of organizing raw thoughts into notes and reminders. Notes and reminders live in the same place, so they’re connected. No need to context-switch between tools or manually link related ideas.
Low friction compounds. I journal more. I remember more. I stay more connected to the people I care about. The best journal is the one you actually use, and this design keeps using it feeling effortless.