On Subscriptions (Part One)

Over the last few years, the number of subscriptions I have for apps has grown by quite a bit, and a lot of apps that I’d previously bought on their own have transitioned to subscriptions. I wanted to spend some time on my thoughts on what I’ve found worth it and why that might be; perhaps as an encouragement to others to try certain apps in spite of their subscriptions, or maybe as a bit of catharsis to justify what I spend on apps that will just go out to the void.

As it was well-put on Mac Power Users, there’s a lot of good reasons for an application to change their business model to be based on subscriptions. It creates sustainable income for developers when the current models are failing. Apple takes quite a bit of blame for this in their lack of support for the traditional model of versions and upgrades with the App Store on both Mac and iOS. Additionally, Apple has encouraged it via a better revenue split for developers on the second year of any subscription.

But as a user, each subscription has to be justified. In theory, any purchase should be justified, but up to a certain amount, I personally have a pretty low bar for an app purchase if I think I ever might get use out of it. But if I have to pay for it again next year, I have to ask myself if it’s worth that money this year.

And even for apps I know I get use out of, it’s not always an obvious slam-dunk for a subscription. If I can see how the feature roadmap benefits me, then I might be more inclined to go forward with a subscription. Or if I can see where the recurring costs (usually in server hosting) for a developer are, then I’m more sympathetic. But I know I’m not totally consistent in my reasoning — and my choices might be totally different from someone else in very similar shoes, and if someone were trying to break these down as a market study, it might be totally useless data.

Great Subscriptions

The first app I can remember subscribing to is Bear. I was unhappy with how I was using Apple Notes, and an article on The Sweet Setup persuaded me to give it a whirl. At $15/yr, Bear became a somewhat unfair measuring stick for the value of other apps. It’s usable without that subscription, but only technically — sync is locked behind that paywall.

Bear doesn’t run its own servers for that sync, but rather syncs through iCloud. The subscription entirely goes to the cost of development, but it’s a totally reasonable fee to me. Bear launched originally as an upfront purchase app before being one of the earlier popular apps to have a subscription fee. I never got in before it was subscription-only.

Some Bear users are a bit upset that updates aren’t faster, but the developers are actively working on a major rewrite of the editor and are very responsive. Many users want to see a web version which is apparently coming, but is probably more than a year off. I’m very happy with the way things are in Bear, though, even if I will appreciate a lot of the new features coming.

Overcast is the app I could most easily get away without subscribing to. Its free version is more than comprehensive, and if I needed to save the $10/yr all of the sudden, I could live without its premium features. It’s supported by some very reasonable ads without the subscription, reasonable enough that back when I was on an iPhone 6 Plus, I actually kept the ads on after I was subscribing because I felt the UI was more balanced with them on. Since upgrading to an XS Max in 2018, I’ve turned them off, but they’re just ads for podcasts.

I don’t pay that subscription to get rid of the ads, obviously. I pay it for the very useful feature of being able to upload any audio file I want and listen to it with Overcast’s powerful Smart Speed (and other audio adjustment) features. This is most useful in using youtube-dl to pull the audio from a video that I really only want to listen to, and being able to consume it faster and without giving it more attention. There’s a post brewing on that workflow.

Jumping up in price, Drafts has, since moving to a subscription model, been $20/yr, but starting in 2021 is now $30/yr for new subscribers (I’m grandfathered in at $20/yr). I wrote at the end of 2018 about the place I found for Drafts in my workflow, and it’s an app that I’m not done writing about. I can’t really do it justice on my own to explain, and I don’t have easy links compiled to break down why it’s so useful, but Robby Burns wrote a great review when it launched version 5, and did a recommendable podcast episode with its developer Greg Pierce.

The subscription funding of Drafts has allowed Greg to go nuts with his development pace. It’s now his full-time job, and he’s put in incredible and powerful features regularly. The features that this subscription adds beyond the free version are really essential for anyone who’s serious about pushing the app to its limits.

I have a love-hate relationship with my email app of choice, Airmail. When I started using it during my student-teaching, it helped me get my email life under control. The number one feature of it to me is that you can extract a URL scheme for every message on both macOS and iOS.[1] This is incredibly valuable for being able to point to a message from another app; I can have a Bear note on a certain topic and reference the emails on it. I can have an OmniFocus task to reply to an email or follow up on the action of an email (when that’s the appropriate way to manage it, which it often isn’t). Airmail has a bunch of other features I like, but none of them are as important as its URL schemes.

It has a Markdown email composer (on Mac but not on iOS) which lets me write long informational emails to families in Drafts with appropriate links and styles in Markdown, tag them and archive them in Drafts (rather than deleting the Draft) so I can look at it in future years and reuse parts of it, and then send it off with as little friction as possible. The only problem is that there’s terrible bugs in both their raw HTML editor and Markdown composer; I’ve solved the Markdown bug, but fixing the bug requires me to go through an annoying process every time Airmail updates.

When I started using Airmail, it was a one-time purchase, and despite its many flaws, I was happy to pay a subscription of just $10/yr (in hopes that it would solve some of the flaws and keep development ongoing; only the latter has worked out). When I bought it, it worked great with Alfred’s incredible file attachment actions (thanks to custom work from Alfred’s devs), but it has been broken for some time now and is another reason I’ve thought of leaving Airmail.

Day One isn’t one of the top apps I use, but it has changed how I think about buying apps. I bought it on macOS as a standalone app initially, and after trying to push myself to get into journaling, gave up on it. At first, I felt a bit stung by the app; I thought it was essentially just a glorified notes app, storing text files as a “journal,” not really seeing the utility in it. I wasn’t yet into Markdown, and I didn’t bother to pick up the iOS app, feeling that it wasn’t worth another $10 to me.

Somewhere down the road, though, my feelings about it changed. It was that Sweet Setup article I’d already mentioned, and something about the notion of being able to just take pictures of birthday and Christmas cards into Day One and chuck the physical versions sounded freeing. The notion of going back really began to click, and on top of that idea of putting physical things into Day One, I started to actually get into journaling.

In between I had originally bought it and had this change of heart, though, Day One shifted to a subscription model. Having not picked up the iOS app originally, if I wanted it to sync with iOS, I had no choice but to go forward with the subscription. I think at the time, my calculus was that if I had bought the iOS app originally, the subscription wouldn’t be necessary for my needs at all, which has made me much more willing to jump on upfront purchase apps I see. I’ve seen a lot of them, whether they were of interest to me or not, move to subscription pricing over time, and there’s often a benefit to previous purchase-users if it later goes to subscription pricing. I’m paying $25/yr for Day One; for those who had bought the initial Mac app, they have offered that as a discount from their standard $35/yr for everyone else, which I appreciate.

Which brings me to Fantastical, the app that initially inspired to write this article quite awhile ago.[2]


When I was growing up, I had an email address from around the age of seven, I would guess. I remember loading that email address into Microsoft Outlook the day I finally got it (I played with Eudora instead of Outlook Express as a child on the versions of Windows that had it), and I was hooked. I fantasized about being an adult who could actually get to use the cool features involved in Outlook’s calendaring system for comparing availability. It seemed so neat.

I was a weird kid, but it might have something to do with how much I love apps like OmniFocus today.

For the longest time, I used my calendar app on my smartphone and then eventually on my Mac (usually the stock calendar app) I used it just to manage events that were exceptions. I needed to be able to see at a glance when I’d have a doctor’s appointment coming up later in the month, or when a concert was. There was, in essence, one way I could manage my calendar effectively, and that was the most worthwhile one to me. I knew my daily schedule, so I wasn’t going to use my calendar for that; if I did, I would wind up ignoring my calendar app most of the time, and it would be a slog to find the exceptional events that I needed to stay apprised of.

When I bought Fantastical for Mac, it changed the way I was able to actually use calendars in my life. There are a whole host of great features in the app, but the biggest to me has always been its calendar sets feature. One set could be for the events I just described and another could be for my class schedule. Or for timeblocking.[3] Or my school’s activity calendar. Or, you know, all of the above with me quickly jumping between each one with an easy shortcut.

There’s other great features to Fantastical too — its natural language input and support for dumping into that natural language input from outside sources like Drafts saves a lot of time — but calendar sets on its own made it worth the $50 cost of Fantastical 2. When Fantastical 3 came out and pivoted to a subscription, they also brought a bunch of other great new features, including calendar sets on iOS, and it was a no-brainer. Some of these features require a server-side component on their end (like their new “proposed date” feature) or API access to third-party data that the developers are paying for (like integrated weather data), which further helps me justify the cost to myself, but I think I had subscribed before I’d read about those features. Recently they also added access to the new premium features in their excellent contacts app Cardhop to the same subscription bundle at $40/yr.

I wanted to lay these out for a whole host of reasons including trying to help others justify subscribing to apps that they might have, but my greater motivation was to lay out the case for what I don’t subscribe to, with one app in particular in mind. Looking at my word count, though, I better split that off for a separate post.

  1. For brevity’s sake, I won’t name iPadOS separately from iOS, but I mean to include it every time I say iOS.  ↩
  2. Somewhere over a year ago. It’s been hard to write.  ↩
  3. I’m not doing timeblocking in any super meaningful sense, but I’ve dabbled a bit over the last few months. I have a dedicated calendar and calendar set for it, regardless.  ↩

Fantastical Drafts Actions

I absolutely love Fantastical 3 and happily pay the subscription fee. One unfortunate part of its update though was a change to its URL schemes which broke the actions for it I was using in Drafts. So today, I happily crossed off my to-do list updating the actions. The original actions were made by Greg (AgileTortoise) the maker of Drafts:

Really simple Drafts actions, but no one else had yet updated them on the Action Directory.

Screen Shot 2020 11 23 at 4 15 42 PM

2018 Recap: Apps that I didn’t ‘get’ in 2017

2018 has been a bumpy road, and there are a few things I want to write as a recap on the year. After talking about reading the Bible in a year, I wanted to focus on three apps that I’d tried previously or owned but wasn’t making very good use of.

Day One

I’d picked up Day One for the Mac back at the end of 2016, but I didn’t really get into it (or ever pick it up for iOS). When they went to a subscription model I originally wrote it off entirely. It was a post over on The Sweet Setup that showed me the role Day One could play in my digital life. To summarize his article, momentos, cards, and letters are easily preserved in Day One as memories, in addition to traditional journaling. I’ve also enjoyed using it to keep track of my life through my first year teaching and things happening on the personal side.

It’s still a bit hard to justify the subscription price, but I look forward to one day being able to print these journals, likely for my kids.


I’d heard the Mac Power Users go on about Drafts quite a bit, and tried it myself without it really sticking. It was generally just a substitute for my OmniFocus inbox that wouldn’t get processed. With the release of Drafts 5, things started clicking much better. It wasn’t any specific feature contained within Drafts 5 (though I’m getting great use of Workspaces for literal drafts of things I write), but it inspired me to make other tweaks in my workflow (including adding Bear). Until I upgraded some of my hardware, it also served as a better dumping ground for OmniFocus tasks where I otherwise might let things slip, as well as recording things that would eventually go to Day One or other destinations. It does take a bit of added time to process down my inbox in Drafts, but it allows me to make sure everything really does get captured.

My hardware upgrades in 2018 allowed for Drafts to become even more supercharged though. As a method of capture, speaking into it on my Apple Watch is generally the fastest and most accessible thing I have access to. And I don’t have to be concerned about finding its fit in OmniFocus right away (lots of things wind up getting added to an existing Bear note or just getting put straight into its destination, like an email, from Drafts). Drafts also launched its beta Mac version this year. This makes it that much more versatile of a writing environment. Actions aren’t a part of the Mac app yet, so processing Drafts on the Mac is a bit clumsier than it is on iOS, but it’s freeing having all of my text accessible on the Mac.

Drafts works for me much better than the sticky note systems I see my fellow teachers using. As I process things down, I feel like I’m truly clearing clutter from my life. And as I continue to stress my OmniFocus system, it’s a major bonus being able to separate capture from my OmniFocus inbox many days. Now that it is free to use the basic version, it’s worth a try for anyone who makes major use of iOS.


I’ve always been a fast typist, and the idea of paying for a service to save me time typing was really never attractive. I had a free year of TextExpander from a bundle I’d previously purchased, and I redeemed it this year to see if there was anything to it. For awhile, even with its snippet suggestions, I wasn’t getting very much value, but with the start of the school year I’ve finally found its niche. TextExpander is valuable for me not because of reducing characters typed, but in reducing the amount I’m thinking when writing.

First it was with snippets that format date for files (yyyy-mm-dd) and for the way I want it to appear on printed documents (mm/dd/yyyy). This saved me moving up to the number rows and the little bit of mental energy it took to think through my desired date format and the actual day in my menubar. But I was able to quickly branch out with fill-ins for sending cookie cutter emails (like emails regarding a new lesson book or a blurb at the end of an email explaining to the student that I’ve cc’d their parents). It’s not just having my words thought through ahead of time, but when I’m filling forms, the way multiple parts of a snippet can draw from a single field (e.g. if I properly set up a snippet, I can have a student’s name filled in everywhere I need it after I’ve typed it once). I sometimes feel a bit self-conscious about using these snippets when emailing parents, but I also know there’s no shame in trying to cut down on the number of hours I’m working right now. I spend a lot of time torturing myself over phrasing in emails home, and being able to reuse my own words where I can may allow me to have time in my life outside of work.

TextExpander and Drafts both allow for JavaScript to make actions more powerful, and if my life gets any less crazy in 2019, I’ll hopefully find the time to learn the skills necessary to make use of these features. On top of this, OmniJS is coming to OmniFocus (hopefully) in 2019, and there are a lot of things in OmniFocus I’d like to accomplish that I think this will enable. I’m not sure what the best way to learn JavaScript is solely for automation, but I picked up a great deal on m1m0, though practicing some of these early skills has been hard.

Managing Multiple Drives and Managing My First Year

I’m well into the start of my first year teaching now, and things are crazy. I wanted to first share a tip I’m using to manage some of the work I’m doing on my own computer for work (I have a PC assigned to me by my school, but I’m working a lot outside of the school day).

I have my primary personal Google account set to my “default” Google account in my browser. The primary benefit of this is that if I click a link to a Google Doc anywhere on the web, it goes into that account (which is the behavior I want). The downside is that when I’m opening up a new tab or window for Google Drive in the middle of work-related things, I’d have to click the account switcher, select my work account, and then wait a second for Drive to reload while closing the first tab. It’s a small inconvenience, but it adds up doing it a lot.

Instead, I’ve bookmarked the Drive URL that I have after switching to my work account. It should be something like drive.google.com/drive/u/(number for that account)/my-drive. Your default account is 0, then each one down the list is another number.

To speed up getting there, I usually launch the bookmark from Alfred, as I don’t keep the bookmark tab open for Safari. It’s a pretty simple solution to a pretty simple problem, and I could always use a different web browser for work matters (but I don’t want to).

App updates

OmniFocus 3 has changed the game for me. I was part of the TestFlight for OF3 for iOS, and I’m now in the beta for OF3 for Mac. Tags and better perspectives are helping me manage a ton of work. I’m a bit disappointed that OF3.0 for Mac lacks support for the advanced notifications that OF3 for iOS has, because I’m still taking out my phone to set a reminder notification for tasks. It’ll come in a point update that I”m already excited for.

I’m constantly restructuring my projects and tags to make them work better for me, but it’s not a time sink, it’s just a chance to organize better. I have so much on my plate at work that I think I’d have a nervous breakdown without OmniFocus to keep track of it all.

I’ve finally got Drafts integrated into my workflow. Drafts 5 added some really nice features, and it’s a great fit. Part of the reason it was so essential is because of some degradation of my iPhone 6’s speed (which will cease to be a problem within the month), but it continues to be the first thing I open when someone tells me something in the hallway that I can’t forget. Most of it goes into OmniFocus still. Because of how little email I compose on iOS, I’m still not getting the most out of it, but between updates to my phone or Drafts coming for Mac, it will only be more useful soon.

I’m planning to write soon about how my adoption of Bear has let me keep track of the documents and emails for rehearsals and individual class periods, why Dorico has won me over, and how I’m getting great use of Pages for making materials.