2021 State of the Tools

Most years (2017, 2018, 2019) I like to take a look back at the tools I found myself using and reflect on the extent to which I’m satisfied with them. While it’s certainly a good practice to be deliberate with the tools I choose to learn and use, this is also my attempt to get my tool stack feeling as solid as possible before heading into the next year so I don’t waste my time fiddling with it later.

A few general thoughts, before diving into a more detailed breakdown:

As I mentioned a few weeks ago, I’ve been leaning into not replacing my core technology as frequently as I have in the past. That means I successfully made it through the most dangerous time of the year for an Apple fan, the fall product releases, without replacing anything in my setup. To be clear, I’m not exactly using ancient gear here (M1 MacBook Air, iPhone 12 Pro Plus, Apple Watch Series 6) but I’m not the absolute bleeding edge, either. That feels right for where I am in my life right now. My hardware is not a bottleneck in my productivity in any way and while it’s fun to have the latest and greatest, I’d rather focus on the work I can accomplish with the tools rather than the tools themselves.

I gave away my iPad Pro to a family member early in the year and haven’t replaced it. That’s partly because Apple hasn’t released a new iPad Pro that felt like enough of an update to justify buying it. At this point, if I’m going to get a new iPad Pro I should probably just wait for whatever the new one will be. Considering my overall trajectory of reducing and simplifying my hardware stack wherever possible, do I even need an iPad? The past year is telling me that I obviously don’t. We’ll see…

With those preliminary thoughts out of the way, let’s dive into an area by area breakdown of what I’m using and how I’m feeling about it.


  • Apple wireless keyboard & mouse (old)
  • Kindle Oasis (2018)
  • HPZ 27” External Monitor (2019)
  • Logitech Webcam (2019) & Blue Yeti mic on a boom (2019)
  • AirPods Pro (2019)
  • M1 MacBook Air (2020)
  • Apple Watch Series 6 Cellular (2020)
  • AirPods Max (2020)
  • iPhone 12 Pro Plus (2021)

Nothing about this needs to change in 2022. I hope nothing breaks and I can just go through the entirety of next year with this exact setup.


Most of the year, as it has been basically every year I’ve done this, my browser across all devices has been Safari. It’s hard to beat Safari for integration with the operating system, privacy, and overall speed. Sure, every once in a while I hit some sort of weird wrinkle on a website and need to fire up my backup installation of Chrome, but 99% of the time Safari is what I reach for to surf the web. That is, however, until the past couple weeks.

Recently my work has taken me into the world of crypto and one of the first things I learned is that Safari couldn’t be my daily driver and also my default crypto browser. So, it looks like I’m going to be splitting time between Chrome on macOS and Safari on iOS (for now). I’ll probably end up trying Chrome as my default on iOS sometime soon, just to see if having it be the same everywhere is worth it.

Previous Years

  • 2017: Safari
  • 2018: Safari
  • 2019: Safari


Spotify and Apple Music have been locked in a pretty even battle for my attention for the entirety of the time they’ve co-existed. I’d go for a few months using Apple Music (whose design and UX I tend to prefer) and then I’d switch to Spotify (whose recommendations are far better). This year, for the first time in a long time, I’ve been almost entirely in the Spotify camp. A major sign that things have gotten more stable with my Spotify usage is that I find myself looking forward to the Discover Weekly playlist update every Monday. I think Spotify is likely here to stay.

Previous Years

  • 2017: Apple Music/Spotify
  • 2018: Apple Music
  • 2019: Spotify


I’ve been all in on Overcast basically since the day it came out. I’m a huge fan of its simplicity and reliability. It hasn’t gotten any sort of visual refresh in a long time, but I honestly haven’t been bothered by that. My goal is to interact with my podcast player as little as possible; so long as the UX doesn’t get in the way of that goal, I’m happy.

Previous Years

  • 2017: Not recorded, but probably Overcast
  • 2018: Overcast
  • 2019: Overcast


This year saw the biggest change to my email that I’ve had in a long time. After successfully avoiding the Superhuman hype for a long time, I eventually caved and tried it out. Turns out it’s really, really good. Would I use it if my work wasn’t paying for its painful $30/month subscription? Probably not. But if someone else is willing to pick up the tab then I’ll happily use it. It’s fast. It’s clean. It’s simple. It’s everything I want in an email app, really.

Previous Years

  • 2017: Apple Mail/Airmail
  • 2018: Airmail
  • 2019: Airmail

Notes & Writing

It’s another year of Bear and Ulysses serving the majority of my writing needs. Most of my writing starts in Bear. It holds ephemeral notes that I need for just a short period of time, notes related to active projects that tend to live for weeks or months at a time, and it’s even the starting point for longer form writing. Once I’m ready to turn something into a piece of longform writing (like this article), I’ll move it over to Ulysses and finish it there. This writing duo has been solid for the past three years and I’m more or less happy with it.

New to the group this year, though, is Obsidian. After struggling with the concept of “digital gardens” and “Zettelkasten” I decided to really experiment with setting up one of my own. I think it’s still a bit of an open question whether it becomes a crucial part of my writing process, but for now my nascent Zettelkasten system is living in Obsidian.

Previous Years

  • 2017: Bear/Byword
  • 2018: Bear/Ulysses
  • 2019: Bear/Ulysses

Read Later & RSS

This is another part of my software stack where I pretty consistently get a bit of a wandering eye but almost always end up back where I start, Instapaper. That didn’t really change this year. I went through a phase of using Apple’s integrated Reading List (again) and even poked around Pocket (again), but ultimately I came back to Instapaper. Something about its limited feature set, simplicity, and how well it handles me throwing things at it from lots of different places has made it a really solid part of my workflow. This year I started playing with Readwise and it has helped make my Instapaper archive an even more helpful place as it surfaces old notes and highlights.

RSS-wise, I’m happy with my Feedly/Unread combination that has been pretty solid for the past few years. Unread feels really snappy and has an awesome feature where double tapping an article automatically saves it to Instapaper.

Previous Years

  • 2017: Instapaper & Reeder
  • 2018: Instapaper & Feed Wrangler/Unread
  • 2019: Instapaper & Feedly/Unread


I’ve become a much bigger proponent of hyper-scheduling/time blocking as a productivity practice so I’ve been leaning on my calendar software much harder than I have in the past. Luckily, Fantastical is a truly stellar piece of software. I love having different sets of calendars I can hide/show with the click of a button because I tend to work with different colleagues on several teams at once. Being able to see our different calendar configurations very quickly is amazing.

There’s a cool new kid on the block, Cron, that is trying to be the Superhuman for calendaring. I’ve played with it a little bit… and it is pretty good, so I’ll be keeping an eye on its development over the next year.

Previous Years

  • 2017: Fantastical
  • 2018: Fantastical
  • 2019: Fantastical


Not much to say here. Things remains the bedrock of my task management system. A rock solid piece of delightful software. Considering how frequently I use it you’d assume I’d have found and been annoyed by all its rough corners. That’s the thing, though — it doesn’t have rough corners.

The only frustration I have with it, and it’s not even really a problem with the software, is that I occasionally work on projects with colleagues where we’re using a shared Kanban board in Trello or Notion as a project management tool. In those cases I end up basically manually syncing my Things database with those tools, which can be annoying and error prone, but it’s not the end of the world.

Previous Years

  • 2017: Things
  • 2018: Things
  • 2019: Things


I’ve always felt weird and bad that I’ve basically split my electronic library across two incompatible services: Apple Books and the Amazon Kindle. This year, I decided I’m going to default to buying my books from the Amazon Kindle ecosystem so that I always have the option of using a Kindle to consume them. I don’t mind reading on my phone, and in fact read almost the entirety of War and Peace on it this year, but every once in a while it’s nice to use a purely dedicated device for reading. If I want to do that, I need to buy my books from Amazon. So, that’s what I’m (mostly) doing.

Previous Years

  • 2017: Apple Books/Kindle
  • 2018: Apple Books/Kindle
  • 2019: Apple Books/Kindle

Stuff That Hasn’t Changed Much Recently But I Still Use and Enjoy

I don’t have much to say about these other smaller utilities other than many of these have become solid contributors to my overall tool stack. Everything in this list has been the same for at least the last two or three years.

Stuff I’ve Stopped Using

And on the other side of that coin is the stuff that I’ve stopped using. Sometimes it’s because I’ve found a tool that does something better than what’s on this list and sometimes it’s because whatever job this tool was filling is no longer something I need done. Many of these are great and worth checking out!

2022 and Beyond

As with everything in my life, I’m always looking for ways to simplify. One way of simplifying is to avoid using specialized apps wherever I can and learn to get by with the default apps Apple provides as much as possible. I’ve run that experiment many times, and I’m sure I’ll have some moments over the next 12 months where I’m feeling overwhelmed and wanting to take drastic action in that direction, but I’m going to do my best to avoid any new Default Apps Only experiments. They tend to be quite disruptive to my workflow and they never stick for longer than a week or two.

Instead, I’m going to be on the lookout for ways to either a.) learn my current tools better so they become even more seamless and simple to use and/or b.) look for workflows that I no longer need or want in my life — meaning I can jettison the tools associated with that workflow. I already run pretty lean, so I don’t think it’s super likely that’s a path I’ll be exploring much in the next year, but it’s always possible.

Honestly, the best thing I can probably do for my sanity, productivity, and minimalist desires is to completely forget about everything on this list until I sit down 12 months from now and write my retrospective on 2022!

I’d love to hear about the tools you use and love. Let me know on Twitter or by shooting me an email.



Organization design guy at The Ready.

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