Tracking Subscriptions

Subscriptions are increasingly common and show no signs of going away, regardless of what you may think about them.

With subscriptions being an important part of modern digital life, it seemed wise to find a way to keep track of them. First I turned to Bobby, which is an iPhone app that has been mentioned a few times on Mac Power Users for managing subscriptions.

Having used it quite a lot now, I can say that Bobby is both great and frustrating.

Bobby’s Best Bits

It’s great to be able to set the name, price, and “cycle” (usually monthly or annually) of a subscription. Bobby has a lot of services already built-in, which will show the appropriate logo and colors for the service. Once you have your subscriptions added in, you can see the average price you are paying on a weekly, monthly, or annual basis.

Perhaps the best feature is the ability to have Bobby remind you when a subscription is coming due. You can set it to remind you the same day (don’t do that, it might be too late to cancel), or 1-30 days/weeks/months/years before it’s due.

(Not sure that “years” is a necessary option. Does anyone have a subscription that they want to be reminded about a year before it expires/renews?)

I wish Bobby let me set a default reminder. Generally I want a week’s notice on all of my subscriptions, with a few exceptions (no need to tell me Netflix is renewing, thanks), but the default in Bobby is for no reminder, and the setting is not shown by default. (More on that below.)

We’ve all had the experience of getting an email saying “Thank you for renewing your annual subscription!” for a subscription that we had forgotten about and would have cancelled if we had remembered it. Bobby can help you avoid that, but you have to remember to add it each time.

Bobby also looks very nice. The fact of the matter is that most of us could very easily just create a spreadsheet with all of this information in it. But we don’t. (Ok, except for you in the back, frantically waving your hand. We see you, and we’re all very impressed. Now sit down.)

I much prefer to look at this:

My Subscriptions in Bobby

…than at some dry and boring spreadsheet. Until I used Bobby, all of my attempts at tracking subscriptions had been short-lived. Now I think that I’ll keep at it, using Bobby, despite some problems and frustrations.

It’s worth talking about those problems and frustrations, even though I don’t think any of them should stop you from using Bobby. If nothing else, you can learn from a few of my mistakes.

Bobby’s Bothersome Bits

Here’s the UI for entering a new subscription.

two Bobby screenshots, one showing ‘More Options’ expanded

(This particular screen is for adding a subscription for a service Bobby doesn’t know about, which is why it looks fairly plain. But I want to focus on the text and fields here anyway.)

On the left side is the default screen that you see whenever you are adding a new subscription. The blank space at the bottom is usually filled with the iPhone keyboard, which you’ll need for entering in the price, name, and (optionally) a description.

The right side is the same screen as the left, except that I have tapped on “More Options” to reveal, well, you know.

The fields for Color, First Bill, Cycle, Duration, Remind Me, and Currency are selected by tapping and choosing from various “pickers” rather than typing.

“First Bill” is not the same as “Next Renewal Date”

I made two mistakes with the “First Bill” field.

The first one was a minor edge case which I only discovered because I was using a Bluetooth keyboard with my iPhone: you can get to the “First Bill” field by pressing Tab and typing something like “2020-02-06” but the app will not recognize a date entered like that, so you need to tap on the field and choose the date from the date picker.

The second mistake was, in hindsight, both more obvious and more frustrating. The field quite clearly says first bill, but the dates that I entered were for the next renewal date. I did that mostly because those are the dates which are easiest to find. I have no idea when I first started using some of these services, and I mistakenly thought that what I should do was put in when I was going to have to pay for these services again.

That, as it turned out, was a significant mistake, because if the “first bill” date is in the future, then Bobby will not include the subscription amount in the monthly estimate until that date occurs.

So, for example, if I told Bobby that my “First Bill” for Dropbox was not until, say, October 15, 2020, then Bobby assumed I was not paying for Dropbox between now and then. Now, I don’t remember when I first started paying for Dropbox (it’s been several years), but what I should have done is put in “October 15, 2019” so Bobby would know that a) I am paying for it now and b) it will renew this year on October 15th.

At first, I found this baffling. Why would I want to track subscriptions unless I am paying for them? Are there people who make plans to start subscriptions at some point in the future?

The only subscription that I could see using this for was Apple TV+ which I have for free until November 2020 but then will renew at its usual price, but that is a rare exception.

Having thought about it further, I assume that this feature is intended to be used when you start a free trial. For example, if you sign up for a free one-week trial before you start paying, you could enter the subscription info into Bobby (along with a reminder, in case you want to cancel before the free trial ends).

Once you know how it works, it is easy enough to adjust. I went through and changed all “2020” to “2019” for any active subscriptions, and that seemed to get Bobby to understand that these were all active subscriptions.

Having said that, if I could change only one thing about Bobby, it would be to change “First Bill” to “Billing Date”. If I choose a date in the future, Bobby could ask me if I want to include the cost in my monthly subscription costs starting today. It seems like a solvable problem, but in the meantime, it’s easy to overcome once you know the system.


If I could change two things about Bobby, the second would be that I would not have “Cycle” hidden under “More Options”.

Maybe I’m unusual (don’t answer that) but most of my subscriptions are annual not monthly. In fact, in looking at my subscriptions, I have 10 which are monthly but 26 are annual. That’s a significant difference.1 The default “cycle” for subscriptions in Bobby is monthly which I can understand, since most subscriptions do have a monthly option. However, because the “Cycle” field was not shown by default, I made the mistake (several times) of setting annual subscriptions as monthly, which will really screw up the budget projections.

(Aside: If I could change two more things in Bobby, it would be a) let me set a default reminder for all new subscriptions and b) let me always see the “More Options” screen without having to tap to expand it every time.)

Again, here’s my list of subscriptions in Bobby:

This is a very visually pleasing screen, and you can see that Bobby has done very well identifying most of the subscriptions that I use.2 Under the amounts, you can see time-frames listed (6 months, 4 days, 3 weeks, etc.) which shows how long until that subscription comes up for renewal. That’s great, but I wish there was some indication of whether each subscription amount shown was per month, year, etc.

I’m not great as visual design, but I think it would be possible to put the subscription length after the price. So, for example:

Apple Music – $15.00

would become

Apple Music – $15/month


Dropbox – $120.00

would become

Dropbox – $120/year

You could even abbreviate “mon” for “month” and “yr” for “year” if needed. I would also drop .00 from prices. I tend to round-off all of my subscriptions anyway, because I’d rather see “$100” than “$99.99”. As I said, maybe I’m unusual.

My last frustration with Bobby is that there is no iPad app. I would love to see an iPad app, and ideally even a Mac app, because it would be so much easier to enter all of this information on my Mac where I could search my email for receipts/renewal information, and then enter it in Bobby.

Beyond Bobby

I really like Bobby and I’m glad that someone created an app like this. For $1 you can unlock unlimited subscriptions, but for $2 you can unlock all of its features and the developer will get a whopping $1.40 after Apple takes their cut.

That said, once I started tracking this information, I found a wanted a bit more. For example, for subscriptions outside of the App Store, I wanted to keep track of the URLs for changing or cancelling my subscription. I also wanted to know which payment method they were set up to use (I have a few subscriptions which are business expenses, so I want to make sure they have the correct credit card information.)

I also wanted to put any contact information that I had for the service, and if there’s one time when companies want to make sure you can contact them, it’s when you’re going to give them money, so subscription renewal emails are a good place to find contact info for each of these subscriptions.

Eventually, I did make that boring and ugly spreadsheet that I mentioned above, specifically so that I could add additional information.

Having it in a spreadsheet also means that I can see the data in other ways. For example, I made columns showing the monthly and annual price of each subscription. It’s one thing to know that I’m paying $18/month for YouTube, but when I realized that also meant I was paying $216/year for YouTube, it really brought home how expensive it is to hate commercials as much as I do.

As I mentioned, Bobby does have a reminder system built-in, but I still wish that I could see my subscriptions as a calendar in my calendar app.

I also found myself wanting to “group” subscriptions. For example, there are just some which I would never consider doing without; then there are some that I feel like I need to have even if I don’t love them (hello, Office 365); then there others that are support that I give mostly just because I want to (Six Colors, MacStories,, TidBITS, and Patreon).

Then there are weather apps. Until I compiled all of this info, I didn’t realize how many different weather apps I was paying for, ranging from $5/year to $25/year.

So when my subscription to forecast data through iStat Menus Weather came up for renewal, I realized that I could probably make do with one of the other weather apps that I was already paying for.

Pro-Tip: If you use iStat Menus via Setapp the weather data is included in your Setapp subscription price. I had bought iStat Menus before I started using Setapp, but now that I have Setapp, I decided installed iStat Menus through it, so I could keep using iStat Menus weather,. Setapp also includes Forecast Bar. I’m using them both. And Carrot Weather. Yes, I currently have 3 weather apps in my menu bar, and no, I don’t have a problem. What I do have is a forecast predicting up to 22" of snow.

This is harder than it sounds

What has amazed me is how difficult it actually is to track down all of my different subscriptions. I’ve been doing this for quite awhile and I still keep finding myself saying “Oh! I just thought of another one” including (literally as I was writing this) Setapp.

People used to criticize Apple for making it too hard to find your subscriptions list. It’s much easier now, just go to the app update screen on your iPhone or iPad and you’ll see it right near the top:

Screenshot of App Update screen

But the truth is that App Store subscriptions are easy to find and manage. It’s all of the other subscriptions that are harder to remember, but it’s worth taking the time to pay attention before you get another email thanking you for renewing a subscription that you had entirely forgotten about.

I thought I had a pretty good idea of how much I was paying in subscriptions, but seeing it all in one place surprised even me. It also got me to go ahead and cancel some of these that I no longer really need.

What I should do next is tally up the cost of my domain names. But… I really don’t wanna. A few years ago I had a terrible habit of collecting domain names, and they’re overly hard to let go. As I write that, I realize how stupid it is, but it’s true, and I suspect others can easily relate. Seeing those totalled would no doubt spur me to cut a few loose. After all, each domain name is probably worth about the same as a month of YouTube without commercials.

Update 2020-02-10

Someone on the Mac Power Users forum reminded me that David Sparks posted a Subscription Database (which is really a Numbers spreadsheet) that is set up to help you track subscription costs, and uses some spreadsheet calculations to do some of what I am doing by hand in my spreadsheet. Worth checking out.

Short URL for this post:

  1. I also have two subscriptions which are 24 months, one which is 36 months, and one which is 10 years. 150 points if anyone can guess what it is. 
  2. Bobby did not have an icon for Acorn, and when I added it, Bobby automatically chose the icon of a squirrel, which I thought was extremely clever. I realize that it was probably just random, but I like to think it wasn’t. Oh, one more item for the Bobby wishlist: let me use my own images, rather than just selecting from Bobby’s selection of icons. 

David Sparks released a new Field Guide for Shortcuts. You should absolutely buy it.

I’m on the record as having been completely wrong about Shortcuts (neé Workflow) for iOS. I was convinced that Apple would never allow it as a third-party app. Even after it was initially approved, I was sure that one day the Workflow team would release an update, and someone on Apple’s review team would realize that this app never should have been approved. So I pretty much ignored it.

When the app was acquired by Apple, I was equally convinced that Apple would kill it, cripple it, abandon it, or otherwise ruin it. “Obviously” Apple just wanted the developers, but the app was unlike anything Apple had done with iOS before, so why would anyone believe that it had any kind of future at all?

There are rare occasions in life when you are very happy to be very wrong.

However, the practical implication of my assurance that Workflow had no future was that I never learned how to use it. When Shortcuts came out as an official Apple app, I felt completely lost. Fortunately, David Sparks of Mac Power Users fame published a “Siri Shortcuts Field Guide” — a video course which demonstrated how to go from knowing nothing about Shortcuts to learning some advanced techniques. I jumped in with both feet. I downloaded all of the videos and watched them on my Apple TV with my iPad in my lap. At the end of the videos, I felt very comfortable with Shortcuts, and ended up making over 150 Shortcuts. Some of them are fairly simple, but some of them are fairly complex (I mean, they aren’t Federico complex but they were respectable.)

Just when I got good at the game, it changed.

When iOS 13 was announced, Apple also announced significant changes to Shortcuts. First of all, it would no longer be a separate app that you have to download, it would be a part of the OS. As a result, Shortcuts would be gaining great new functionality — Hurray! — and also be changing drastically Hurra — wait, what?

I was actually frustrated by this announcement. I’m not proud of that. I think it’s a function of getting older and being less mentally flexible, which isn’t something I’m happy to realize or admit. There was a time when any new software release for send me deep-diving into every corner, nook, and cranny exploring and looking for new things. (I used to go through each pane of System Preferences looking for new things when macOS updated.)

To be fair, I tried to keep up. I installed the iOS 13 public betas with the full intention of trying to learn the new ways of doing things. But as you’ve probably heard, this year the betas for iOS have been rough. When I started to hear about iCloud problems, I immediately backed off the betas and stopped using my iPhone and iPad for all but the bare necessities — and many of those didn’t even work!

Eventually I did look at Shortcuts, but so much had changed that it felt strange instead of familiar. I tried a few things but when something didn’t work, I was left wondering I was doing it wrong, or if I was finding bugs in the system. Overall, it was just frustrating.

When I heard David say that he was updating his Shortcuts Field Guide, I was relieved.

When I heard him say that he was basically having to re-do the entire guide and planned on releasing it as a new, separate guide, I nodded in complete understanding. Even some of the basics have changed. It’s almost like the third time that the app has been a “Version 1.0” — once as “Workflow”, once after being acquired by Apple and renamed “Shortcuts”, and now again as “Shortcuts integrated with iOS”.

The good news is that I think this third iteration is likely to stick around longer than the previous two. I have no actual insight into Apple, Inc., but I wonder if perhaps Shortcuts had to go through these transitions before being fully “adopted” by Apple as one of its own. Since it is now part of iOS, I think the transition is complete.

The Challenge and the Opportunity of Shortcuts

The challenge with Shortcuts being on its third major revision is that there is a lot of outdated information out there. Trying to find current and accurate information is challenging. Some of the old ways no longer work, some of them have newer and easier alternatives, and some of it was simply not possible before. If you simply head to your favorite search engine to find help, you could end up frustrated and confused. That will improve over time, but right now, it’s a significant hurdle.

That doesn’t mean this is a bad time to get into Shortcuts. In fact, I would say just the opposite. If you have not spent time with Shortcuts before, or if you have but realize that a lot has changed, then you know the opportunity is just waiting for you to create ways to make life simpler for yourself through the automation possibilities Shortcuts offers.

If you want to make your own Shortcuts, and — perhaps more importantly– if you want to understand the way that Shortcuts works on a conceptual level, then what you want is someone who can walk you through the process. Ideally, you would like to be able to watch as someone who knows what they are doing goes through the steps of building both simple and more complicated shortcuts.

“Shortcuts Field Guide, iOS13 Edition” is David Sparks’ instructional tour, which begins with the “whys and hows” of the foundational pieces, then works up to the intermediate level of specific features and functions, and finally opens the throttle to show you the new advanced triggers and automation power which were never possible before. All along the way, you’ll get to watch how he works, and as he works he explains the choices that he makes, and why. This is the guide that I wanted and needed to get me ready for the next chapter of Shortcuts on the iPhone and iPad.

David combines two special abilities here: first, an extensive knowledge of Shortcuts, and second, the ability and the experience of a teacher.

Being able to do something is one skill; being able to teach someone else to do it is another. In college, I had the misfortune of having a few professors who could no longer effectively teach introductory courses. They could no longer remember what it was like to be a true beginner. David has been doing these video Field Guides for awhile now, and each one has increased his ability to not just describe or show, but to teach, and he does so with the beginner in mind.

If you start with no knowledge, but have a desire to learn, David’s inviting enthusiasm will be all you need to get started, and at the end you will have learned enough to feel confident in your abilities to go forward to build your own Shortcuts. The name “Field Guide” is a spot-on description of what you’re going to get: someone to walk with you through the process of learning how to use this tool in real-life situations.

(If you have used Shortcuts before, you will appreciate that David also includes some examples of how he has updated some of his Shortcuts to take advantage of the new features and functionality now available.)

There are 6+ hours of videos here, but if you’re like me, it may take you longer than that to finish the course, because I kept pausing the videos to create new shortcuts based on things I had learned. David also includes more than 80 shortcuts which he uses in the videos. They range from a relatively simple “record dictation and save text to an Apple note” to a crazy cool “Link-O-Rama” and a complete “Morning Report” including calendar items and weather conditions. Automation does not need to be incredibly complex in order to be valuable. There is great value in creating a “simple” automation to make a common task simpler and less error-prone, or to eliminate a daily friction point that you might not have even realized was there until you saw a way to eliminate it.

I have no doubt that I will revisit this course in a few weeks or months to see what it might spark in me tomorrow that is different than today, but I have already hugely benefitted from the time I spent watching these videos. Oh, and don’t think that you need to set aside 6 consecutive hours. Most of the lessons are under 10 minutes each, so you can watch a few in separate sittings if you want or need to break it up into smaller chunks.


Don’t tell David, but he has vastly underpriced this Field Guide. My son takes voice and guitar lessons. Each one-hour lesson costs more than this Field Guide.

Imagine that you happened to be friends with David in real life, and you asked him to teach you how to use Shortcuts. How much time would you reasonably expect him to spend with you? Maybe an hour or two, at most?

And because you aren’t a terrible person, you’d want to do something nice for him in appreciation of his time. Maybe you’d offer to take him out to eat (somewhere nice, or at least somewhere without a drive-thru window). Or maybe you’d send him an Amazon or Apple Gift Card. $50 would seem reasonable to me.

Now imagine that he spent six hours with you. And he recorded the conversation so you could go back and rewatch it whenever you needed, with chapter markers so you can jump right to the point you want. And he also made several combo videos so you could download them and watch them anywhere, anytime, in any app you choose (no DRM or any of that nonsense), even if you don’t have an Internet connection.

If you paid him the US minimum wage of $7.25/hour, it would be over $40. (You would also be a terrible friend, because who would pay someone with David’s experience and expertise minimum wage?!?. The kid down the street probably gets twice that for mowing lawns.)

What I’m saying is that there is no way that $29 is a reasonable price because it’s way too low. But David has it priced at $29 anyway.

And if you act fast you might even find a $5 coupon, which makes it only $24, which almost seems like stealing. I pay almost that much for my regular order at Five Guys.

If you bought David’s previous Shortcuts Field Guide, this is a separate purchase, and if anyone complains about this I will campaign to have them thrown off the Internet. So much has changed that there was no way he could have just updated the old course. If you bought the old course and want the new one, it’s most likely because you know how much has changed. Did any of us expect last year that Shortcuts would change so much this year? Of course not. But it did.

This was a huge undertaking, and for it to be ready when iOS 13 launches took a lot of work on David’s part. There is an even bigger discount for those of us who bought the previous version, which is a fair and generous move on David’s behalf. Everything I said above about the cost of this year’s course was true for last year’s course as well, so even if we paid full-price for both, we’d still be ahead. So let’s not be greedy, but rather be grateful that not only is Shortcuts not dead but its future looks quite bright indeed. Which means that your investment today is likely to be useful for a long time to come.

Look, just buy it.

If you’re one of the tens of people who will read this post, chances are high that you like nerdy Mac/iOS stuff. This course is absolutely worth your time and money. Go get it.