Weekly Check-in: 11/8

More user tests, more learning

catIllustration by Kelsey Holmes

For the sake of accountability, I am trying to regularly writing check-ins on my work in progress.

See all check-ins here.

Last Week's Update

Every week, when I sit down to write these, it feels like a lot has happened. It's a funny thing, because every day I don't accomplish as much as I would like, but when I look back at the week, it's a lot more than I remember. It makes me appreciate the weekly check-in as a way to zoom out and change my perspective.

At a high level, I was able to do two more user tests of Daybird and came out with a ton of usability tasks. I fixed 19 bugs / usability issues. I also made progress on writing integration tests with Polyglot.

This was also the first week I missed not having a co-founder. There are some activities I'm not good at in the entrepreneurship journey and unfortunately, hearing user feedback is one of those. I want to push myself though and see if I can grow in this area.

Finally, I had 8 social meetings and am grateful for this time to be able to rebuild my social circle and spend more time on family. Other than not making money, this season of life has been quite amazing, and it tells me that I'm on the right track in life.

Learnings of the Week

I started the week feeling pretty down on Daybird - I didn't feel great about the prospects for success given I haven't gotten anyone to use it consistently.

Having done two additional user tests, I saw that the promise of Daybird (daily planning) resonate with people and cause them to want to sign up. Both users ran into problems after sign-up - the actual implementation of tasks and notes caused a lot of confusion. The encouraging part is that this is a product / engineering challenge, which should be in my wheelhouse.

I have clarity on a few new pieces to build. The main one is re-thinking how people add tasks - having users type [] to create a task has been consistently confusing, so I'm going to transition to a Notion-style / menu to insert any type of content. I wanted to avoid that since I personally dislike that UX, but Notion is doing great and I think that battle's been won already.

(Sidebar: keyboard-shortcut driven interfaces are great for power users but not user friendly. This is a big difference between myself and most users.)

All of this reminds me of Astrid - when we started user-testing Astrid regularly, I saw a bunch of areas that users got confused that. When we spent the time to fix those areas, we saw big retention gains, which makes sense - confused users stop using products.

Something else: from one user test, one potential area of conceptual confusion on Daybird is the Today note, and how that works with other notes. People will start writing in the Today note and realize that what they've written belongs somewhere else. Then they have an impulse to "re-organize" or their stuff is forgotten.

I wonder if this is where #tags might be helpful. That way, you don't have to create new files - just tag your note with #usability and you can find it later.

Win of the Week

Based on last week's user feedback, I experimented with a few ways to make Daybird a little more visually interesting. I settled on a gradient sidebar, where each color is generated based on the day you're viewing. Each day gets a slightly different color. It's subtle but I think it's really pleasant.


  • Q4: Polyglot released with 3 active users

    • Made some good progress on integration testing, but then I got sucked back into Daybird. I'm a bit concerned that this isn't on track, but I want to leave Daybird in a good place before moving on. I don't like multi-tasking.
  • Q4: Daybird released with 10 active users

    • Continuing on the usability theme, it feels closer to ready. I think two more rounds of testing should be sufficient.
  • Q4: Ride 270 miles

    • 68 miles down, 202 to go

On that last one, it's been tough to feel like I have enough time to bike, so I'm going to try to get my indoor setup going.


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