I care about the software I use. It should be fast. It should be well-designed. It should have a clear business model (as a predictor of longevity). If all of these things can be accomplished while also being developed by the first party (i.e. Apple), that’s even better.
Communication
Superhuman remains my email client across all devices. It’s ultra fast and allows me to use keyboard shortcuts without modifier keys (i.e. just hitting “E” to archive a message, hitting “C” to start a new email, etc.). That being said, I did spend some time with Apple’s Mail apps this year with very little interruption to my workflows. I don’t like the Archive Message keyboard shortcut on macOS and I have no need for the new Apple Intelligence automatic categorization features, but I do find its design to be otherwise clean and attractive. I’ll be sticking with Superhuman for the time being but if I ever got into a situation where I (rather than my company) had to pay for it then I’m pretty sure I’d bail to Apple Mail and not feel any worse for wear.
The Ready continues to use Slack for all our internal text-based communication even though I feel like I can see it deteriorating. I can’t remember a new feature they’ve introduced that actually useful. It’s getting more complex and worse every day.
We continue to use Zoom as the default video calling service at The Ready and most days I don’t really need to think about it, which is high-praise for a video calling platform. I find myself occasionally using Webex, Teams, or whatever the Google equivalent is called this week when certain clients call for it, and they all feel worse than Zoom.
Loom continues to hang around as a quick and useful way to make and share videos with each other at The Ready and with clients. It has become a mainstay in my asynchronous ways of working toolbox.
Personal text-based communication happens almost entirely in Messages.
Haven’t touched Audio Hijack in over a year but that’s more a function of “Fields of Work” being on hiatus and me not being involved in the production of “At Work with The Ready” (where we use ZenCastr).
Project Management
All my work continues to flow through Things. Emails that represent tasks get forwarded to Things, stray thoughts get captured into Things, next actions from meetings get extracted into Things — basically, anything that needs to become some sort of productive action on my part probably went through Things at some point. I periodically try replacing it with Reminders and it always feels like I’m trying to run through mud. Other than being blazing fast and having rock solid sync between my devices, the key feature that Reminders doesn’t have that Things does is the ability to “defer” a task or project until a certain date (basically, make it disappear from my system until a certain date). I use this all the time to help me focus on the stuff I can only do right now vs. the stuff I know I want to handle in the future.
The slight wrinkle to my Things-based utopia is that I have to work with other people and Things remains a resolutely single player app. The Ready uses Notion for project and knowledge management, so I have several different team-based kanban boards that I’m regularly monitoring and using. I will often manually extract tasks from Notion into Things but that sometimes gets unwieldy. If I could have my various Notion kanban boards automatically stay in sync with Things (and vice versa) I would be in heaven, but I don’t think that’s possible.
I’m no longer on any projects where we use Trello as our shared project management software.
I continue to use Fantastical with a Google Calendar backend. I’m an incredibly heavy user of my calendars because not only do I use them to keep track of upcoming appointments, I turn them into fairly accurate historical archives of what I was working on throughout the day. I experiment with the native Calendar app from time to time and I think I could probably make do if Fantastical disappeared one day. The one feature I’d miss the most, though, would be the ability to hide an event. I have a couple active calendars that are basically information radiators and once an event goes by or I have the information I need in my head I no longer want to see the information but don’t have the ability to delete it.
Reminders continues to hold a handful of recurring reminders I call Life Scaffolding as well as a shared grocery list that I collaborate on with my wife. It also is where I’ll throw any short-term reminders via Siri.
Documents, Decks, and Deliverables
Despite using Notion, The Ready still relies heavily on Google Docs, too. That’s where most of my document creation happens as I haven’t found anything where multiplayer collaboration happens smoother. We use Pitch for collaborating on most decks in real time. We use Mural for collaborating on a virtual canvas in real time (with occasional sojourns into Miro for a couple of client projects this year). I have small gripes with most of these tools but most days they feel pretty smooth and get the job done.
A lot of my early thought gathering happens in the notes app Bear. From there, that text may get shuttled over to a Google Doc or an email or a Pitch deck. I like how it looks and feels and how it handles Markdown. If I’m writing something, it’ll probably start in Bear and it may even stay in there for the duration of a project. If a piece of information is what I’d call a “Reference” it probably lives in Notes, though. For a long time it felt like I had to use Bear or Notes, but not both. I realized there are reference notes I look at pretty regularly (e.g. Weekly Review Checklist, Gift Ideas, hours the pool is open at my gym, the menu for the restaurant I order lunch from frequently) but don’t want cluttering up the space where I’m doing active work. I moved those things to Notes which allowed Bear to be an “active working space” for writing. So far, that distinction has felt pretty good.
Of course, it couldn’t be that simple, as I’m actually writing this in Ulysses. Why not Bear? Bear is for notes whereas Ulysses is where I write longer things that are destined to be articles or newsletter issues. That distinction feels useful in my brain, so I’m rolling with it.
And what about Obsidian? Obsidian is where I try to build an active “knowledge garden” with notes from the books I read, articles I write, and other pieces of knowledge building activities. I guess Notes is where I keep “life reference” material whereas Obsidian is where I keep “knowledge reference” material. It’s a quasi-Zettelkasten but if I’m being honest with myself, I’m not particularly stoked on how I’ve used/nurtured it over the last year but I’m not ready to pull the plug on it entirely.
Browsing and General Internet Things
I spent the vast majority of this year using Arc as my macOS browser. There are lots of things about it that I really enjoy (particularly the sidebar history and ability to put things in a split screen view). A couple weeks ago, though, I switched back to Safari and tried to invest a little bit of time in learning some of the “new” features that I never bothered to learn when they first came out. Web browsing feels like the number one thing to try to keep first party if at all possible. I’m not sure why, but it feels so central to the experience of using my devices I like when I’m able to use Safari across all of them. So, for now, that’s what I’m doing even though I remain a fan of Arc.
I can only go so far with Safari, though. I know it has a read later service built into it (Reading List), but as much as I try to use it I can’t make it stick for me. For 99% of this year I’ve used Matter as my read later service. I’ve been a big fan of Matter for a few years now but just recently started feeling like it’s trying to do too much. I noticed it was actually too good at surfacing other things to read that it thought I might enjoy (it was often right). I’d open the app to read an article I had saved only to be distracted by a bunch of other stuff. In the last couple weeks I re-installed my first read later love, Instapaper, and am going to try using it instead of Matter. I’m guessing its simpler design and less audacious aims might actually result in me reading more.
I’ve tried to get back into using RSS a bit more this year and have used NetNewsWire across all my devices to do so. I don’t remember why I switched from Unread.
ChatGPT (and to a lesser extent Claude and Perplexity) have grown in how much I rely on them throughout the day. I’d say I interact with ChatGPT basically every day. For awhile, I had it mapped to the Action Button on my iPhone so I could invoke it as quickly as possible, too. I’m pretty sure this whole family of apps, particularly ChatGPT, is going to continue gaining in importance for me across 2025 and beyond.
When I left Twitter a few years ago I thought I had maybe excised social media from my life permanently. With the growth of Threads and Bluesky this year, though, I’ve found myself getting pulled back into this world a little bit. I don’t post much on either one, yet, but both have a way of capturing my attention more than I’d prefer. I think Bluesky will become the place where I post more consistently in 2025 and I’ll probably continue to look at both more than I want.
Entertainment
Overcast is the only way I listen to podcasts. If it disappeared tomorrow I guess I could make the Podcasts app work, but there’s so many quality of life features built into Overcast I would miss.
Apple Music has emerged as my default music streaming service. It feels like one of those services where it has advantages over third party apps (e.g. Spotify) in how it interacts with the OS. While its algorithmic recommendations are definitely worse than Spotify there are aspects of its design I like much better. I’m also utterly uninterested in audiobooks or podcasts in Spotify and it feels like they continue to junk up their app with everything other than music.
Audible is where my audiobook listening happens. It’s fine.
I split my digital books between Apple Books (40%) and Kindle (60%). I wish I had one unified digital library but it feels like that ship sailed a long time ago.
I continue to do my sporadic personal journaling in Day One.
Logging what I play, read, and watch happens in Sofa (as well as managing the backlogs for each). I continue logging my reading in Goodreads mostly out of inertia.
Utilities
Weather nerdery continues in Carrot. Travel nerdery continues in Flighty. Training nerdery continues in TrainingPeaks and Strava. Password management is getting annoyingly split between 1Password and the new native Passwords app. Backblaze continues to silently back up my computer. Mela handles the handful of recipes I find myself referring to periodically. Rocket continues to help me put emoji everywhere and anywhere. Magnet got bumped out because macOS gained the ability to snap windows.