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I don’t mean for this blog post to only be more complaining. It’s just my dumb solution to a Finder bug I’ve been running into for years. And also a great example of how a little bit of automation can go a long way. (And an even better example of how unique the macOS ecosystem is that tools like this can exist – and how scared I am that (despite assurances) we seem to be headed in a direction where powerful and clever apps are not wanted.)

Anyway, something must have broken in Finder around when Apple integrated iCloud Drive into macOS Sierra in 2016. That’s when I noticed that the files on my Desktop would stop appearing on…my Desktop.

The bug first caught my attention when I’d take a screenshot and expect it to, you know, be saved to the Desktop. Except the file would never show up. But at some point, I noticed that the files were there. I could ls them in Terminal. They just weren’t visible in the GUI.

I also saw this happening when I’d save files directly to the Desktop from other apps. More curiously, I could force the missing files to appear if I created a new folder on the Desktop. Boom! Something would refresh, I’d see all my files, and I’d delete the temporary folder.

After a while, I eventually realized this bug only happened when I had iCloud Desktop and Documents syncing turned on. That was a bit of an aha! moment for me. Because it seemed to jive with how iCloud Drive just sort of has a “hope for the best” approach to file syncing.

When something goes wrong, you never know about it. Just silent failures with no error messages. (Modern Apple is allergic to error messages.) No way to recover or force a sync to kick-off. At least with Dropbox, you can quit the app and relaunch to get a fresh start. But with iCloud baked into the system, often your only recourse is a system restart.

This all seems like a symptom in line with Gruber’s article from last year titled “What You See in the Finder Should Always Be Correct”. He writes

Everything the Finder displays should be correct all the time…the visual representation of the file system in the user interface should be treated with almost the same amount of attention…It creates mistrust in an aspect of the system that the user should, ideally, trust completely.

And concludes with this perfect analogy.

The Finder should treat every bit of information it displays as though it’s as important as your bank account balance.

And that’s precisely it. I lost trust in the Finder in recent years as I caught bugs like what he described and my own.

But I was stuck. I mean, wow, I loved having my Desktop synced. It was such an excellent addition to my workflow when it worked. It just killed me that having that feature enabled meant I couldn’t be sure if what macOS displayed reflected reality or not.

(A synced Desktop has become such an integral part of how I work with my active project files that it led to this ridiculous experiment.)

While thinking about writing this post, I quipped a snarky tweet a few days ago

If I could go back in time and alter any tech industry decision at my whim, it would be to convince Steve Jobs to acquire Dropbox. It turns out that a folder that syncs reliably is a really awesome feature and would make things so much easier.

It was a reference to my solution to the problem that I mentioned without much context last Summer

sudo rm -rf ~/Desktop
ln -s \~/Dropbox/Desktop/ ~/Desktop
sudo chflags -h schg ~/Desktop

Not for the faint of heart, but it works. And I haven’t caught Finder reporting inaccurate / delayed data since turning off iCloud Drive.

For those who don’t speak nerd, that’s me deleting my Desktop folder and replacing it with another folder inside Dropbox.

And you know what? The missing file bug goes away, and I still get the convenience of a synced Desktop folder.

But there was still a missing piece. The other significant part about having my Desktop synced through iCloud was how easy it made shuttling files from iOS to my Mac.

Many times during the day, I’ll export a file from an iOS app and drop it into iCloud → Desktop in Files.app so I can grab it quickly on macOS and do something with it. I do this all the time with iOS screenshots to capture bug reports and store them on my Desktop to triage later.

So, switching to Dropbox sync made Finder more reliable, but it meant that files I saved from iOS would appear buried in the regular iCloud Drive folder on my Mac – not nearly as convenient a location.

I tried saving files on iOS into Dropbox’s section of the Files.app, but that didn’t sync reliably unless I opened the Dropbox app on my phone to force a sync.

Because that’s the funny dichotomy here. On macOS, for whatever reason, I haven’t found iCloud Drive syncing to be very reliable despite having all the resources of an always-on, not power-constrained OS. But on iOS, because it is more resource-constrained and doesn’t allow arbitrary background processes, Dropbox doesn’t sync reliably – even though iCloud Drive on iOS typically works great for me since it’s baked into the system with extra privileges.

Getting to the point of this blog post, here’s my solution.

Hazel.

I’ve swapped out both my iMac and laptop’s Desktop and Documents folders for alternate locations inside Dropbox using the scary shell script above. This gives me the super awesome, fast, and versioned syncing that I trust. And also keeps Finder in line.

On my phone or iPad, when I want to export a file to my Mac, I save it into Files.app → iCloud → Desktop, since that results in faster and more reliably syncing.

Then, I have Hazel watching that iCloud folder on my (always on) iMac with a rule that moves any file from my iCloud Desktop folder to the one inside Dropbox. (And renames the file if there is a duplicate.)

Within a few seconds (given the appropriate bandwidth), the file from iOS is available on all my devices right where I want it.

I hate to say it, but it works great.

I’ve been trying to stay as busy as possible for most of 2020 for personal and professional reasons. But when November finally rolled around, I decided enough was enough and needed a break.

That didn’t mean a vacation. It was more of an acknowledgment that November was already our busiest month of the year at work. And then there was the US election and the holidays and going back into fucking quarantine more than we already were. Not to mention getting app updates out the door for Big Sur and Apple Silicon.

Luckily, I managed to get most of my commitments done in the first half of the month. Which meant I was able to relax for the next two weeks and just let my mind wander and play around with old and new ideas I’d never given time to before.

Two ideas emerged.

The first is a much larger collaboration with a friend that, if the stars align, I can’t wait to share early next year.

And the other is a tiny little Mac app that I made last week because I needed it in my day job. I’m not sure what to do with it or what will ultimately become of it, but, as usual, I figured I should make the app available in case anyone else finds it useful.

For lack of a better name, I call it Standup.app. It helps facilitate the super-short standup call I run with my team every morning.

It also serves double duty as a weird, helpful presentation utility for the seemingly never-ending stream of video meetings I have throughout the day.

I know there are other solutions, but this one is mine and built to my odd specifications.

Here’s a demo that likely won’t make sense until you read what’s happening below.

Standup.app is meant for when you’re sharing your screen during a video meeting – especially if that meeting is of the standup variety.

It starts by displaying your Mac’s webcam. You can resize and position the window wherever is most convenient.

Start a new timer with ⌘N. Enter how long you want the meeting to last (in minutes) and each participant’s name – one per line. (You could also list the names of tasks or projects if the meeting will use those instead of going person by person.)

Click “Start Standup,” and the meeting begins.

On the right, a timer tics down until the meeting is over.

On the left, it divides the total time by the number of participants and runs a timer for each person’s section – one after another.

The timers go from green to blue to red as they approach zero. When time is up, the app advances to the next person on the list.

(For this demo, I’ve allotted two minutes for six people. That’s stupid. But, this is a demo 🤷‍♀️)

Standup meetings shouldn’t be written in stone or ruled with an iron fist. In my view, they’re just a guideline to get everyone on the same page and the meeting over and done with. So, if one person finishes early, type ⌘P to skip to the next person.

On the other hand, if something comes up that does warrant more discussion, you can toggle (pause) the timer with ⌘T. (You’ll see the two timers dim in the video when I pause).

Ok, now for the strange parts.

The webcam factors into all of this because I use the app for video meetings. Ideally, when you’re on Zoom, or Teams, or whatever, instead of sharing your webcam directly, share your screen or the Standup.app window. This will let everyone see your face and timer at once.

More importantly, though, I mentioned above that I use this app also as a presentation aid. The camera window floats above everything else on your screen so that if your entire screen is shared, you can move and position it above or alongside other windows you’re presenting to the group. This lets you visually narrate right next to the content. In my case, that often means our Jira board or even just Xcode.

As you’re sharing, you can press ⌘↑ and ⌘↓ to adjust the transparency of the camera window. (The time boxes remain visible.)

You can also ⌘/ to toggle the camera off/on entirely.

As I said, the camera window floats above everything else you’re presenting. But that would make using other apps impossible if the Standup window is on top and in the way.

To solve this, when you switch to another app and Standup.app loses focus, the camera window will visually remain on top, but all of your mouse clicks and keyboard input will go to the other app like normal.

In the demo video, I edit and select text in TextMate behind the camera window and do a little light web browsing.

If you need to adjust the standup settings or move the camera window, switch back to the app and do what you need. The redirection of your mouse/keyboard to Standup.app or your other apps all happens automatically.

You can make the Standup window full screen or as small as you want. Make it completely solid or barely visible. I present using different methods depending on the audience and what I’m sharing.

As I said initially, this app is really, really niche – even more so than the other strange things I build for myself. But, hopefully, it might help someone else now that so many of us are collaborating with remote coworkers.

You can download Standup.app from here. It will automatically offer to download new updates if/when I push out any bug fixes or improvements. Your feedback is very much welcome, of course. I’d love to know what you think.

Download Standup.app

Stay safe out there.

The idea for this app started eleven months ago as a collection of PHP scripts and a giant Shortcuts.app shortcut. But I quickly realized it would be best served as a real iOS app. I’ve been working on it off and on since February and have teased it a few times publicly on Twitter.

But now I think I’m ready for broader feedback from outside my small group of testers. And hope that feedback will show that it’s useful to more people than just me.

The app is called Voxmail. And (I think?) it’s the first iOS email client that you can’t use on your phone.

Instead, you check and triage your email using only your voice with Siri.

I’ve been using it every weekday for the past six months (when not quarantined) to go through my inbox while commuting to work. Specifically, I use it with Siri via CarPlay to hands-free get a handle on any email that came in overnight or that morning before I arrive at work.

Voxmail isn’t meant to replace your real email app. It’s meant to augment your mail client so that you can read, archive, delete, mark as spam, etc. your inbox while driving or doing other tasks with headphones on.

The app even has, what I think, is an amazing workaround to give you verbal push notifications of new messages when connected to AirPods or CarPlay. (I hope Apple approves it.)

How does Voxmail work? Let me show you a conversation on my phone with Siri side-by-side with my email client and Reminders.app on my Mac so you can see things happening in real-time.

(Make sure your volume is up so you can hear Siri reply.)

Think of Voxmail like you would old-school cellphone voicemail from the 2000s. The app will read your messages to you one at a time, and you can take action or skip and move on to the next.

Here are some things you can ask Voxmail to do:

• Check my email
• Check my unread email
• Next email
• Go to my first email
• Read that email
• Archive that email
• Delete that email
• Mark that email as spam
• Mark that email as read
• Mark that email as unread
• Flag that email
• Un-flag that email

As a bonus feature, you can also say

• Remind me about that email tomorrow at 4 pm

and Voxmail will add a reminder to the iOS Reminders app with an alert set for the date and time you chose and the email as an attachment.

But what about CarPlay?

Well, one of the things that have always annoyed me the most about CarPlay is that Apple silences all notifications while you’re driving except for a few whitelisted ones such as text messages, calendar alerts, and turn-by-turn directions.

I totally get the safety reasons for this. But at the same time, if my boss sends me a Slack message saying that the world is on fire while I’m driving home and I need to call him, I would very much like to hear that notification via CarPlay. Not so I can try replying in Slack while speeding down the interstate, but so I could hands-free say, “Siri, call my boss.”

My point is that I would like to be aware of other, non-approved notifications – even if I have no intention of ever using my phone while driving. Email is one of them.

Voxmail solves this problem by reflecting new emails to your phone via SMS when you’re connected to CarPlay or Bluetooth headphones.

What does that mean exactly?

During my commute home, Voxmail will periodically check for new email in the background. If it finds a new message, it will send the sender and subject (and nothing else) to my web server. My server then sends a text message to my phone, summarizing any new messages, which Siri will happily announce and read to me in the car or over AirPods.

If it’s a message I’m interested in, I tap the voice button on my steering wheel and say, “Read that email” to hear more.

What about privacy?

Email is a sacred thing full of all your secrets. That’s why none of your email ever leaves your device with Voxmail.

Unlike most other iOS email apps, Voxmail checks your email itself – on your device – communicating directly with your email provider. It does not use an intermediary 3rd party server to proxy your messages. All of your information, including your email account credentials, are kept locally.

The only exception to this is the SMS forwarding trick I explained above. That feature is opt-in and disabled by default. If you turn it on and confirm your phone number, only the sender and subject line of new emails are sent to my server – never the actual contents of your emails.

Further, none of that information is stored in a database. It’s only around long enough to send you a text message, and then it’s gone.

I don’t need your data. I don’t want your data.

So that’s Voxmail. I think it’s a ton of fun and find it incredibly helpful.

It’s not fully featured or quite ready for prime-time yet, but it is now available as a public TestFlight build. If anyone would like to help test, I’d love your feedback.

You can join the public TestFlight here. And I have more documentation available here.

(Click here to skip my boring intro and go straight to the fun stuff.)

It’s been nearly two years since I posted anything significant to this blog’s Productivity and OmniFocus section. A big reason for that is after practicing GTD for fifteen years, I had pretty much nailed down a slightly tweaked take on the process that worked well for me. There was no need to make changes just for the sake of change.

But one significant change I have made is to my morning routine. And it was made possible by OmniFocus’ version 3.4 update last year. I’m sorry that I’m just now getting around to writing about this new workflow because it’s a lot of fun. And it just might be my favorite new feature Omni has ever shipped. As a user, it’s wowing me with the possibilities. And as an Apple developer, I’m amazed at how well done it is.

One of the fundamental tenets of GTD is capturing all the open loops in your head and putting them into your trusted system. I’ve found that making capturing as frictionless as possible in any situation has been one of the most significant net benefits in my life.

But OmniFocus’s Siri Shortcuts allow for something entirely different: Ubiquitous Planning. I can now review my commitments for the day at any time without being visually tied to my device.

I have two young kids, so our morning routine is barely controlled chaos. Add to that a fairly long commute into the office where the last ten minutes is me on the phone for our daily standup call. So, from the time I open my eyes to when I sit down at my desk, I pretty much have no idea what’s in store for the day other than what I remember from my weekly review on Sunday or anything I managed to look over the night before.

My actual planning time is me triaging emails, Jira tickets, Slack messages, notes from standup, and my OmniFocus lists during the 30 minutes after my morning call ends. Only then am I ready to begin work. And by that point, it’s practically already time to start the daily Slack poll for what we’re ordering for lunch, and, well, mornings go by fast.

But what about that dead time in the car on the way to work? Podcasts? Sometimes. Singing at the top of my lungs to 80’s New Wave? Always.

How about stealing back some of that time and doing a daily review? Yep. Now I can.

OmniFocus now has a fantastic Siri Shortcut action that lets you run queries against your task database. And with some clever Shortcuts.app programming (is it really programming?), I’m now able to ask Siri questions about my upcoming day via CarPlay and have the results dictated back to me so I can at least get a summary of what’s available, what’s due, and a reminder of what I completed yesterday.

Let’s start with a simple example.

My OmniFocus Inbox is a dumping ground for tiny reminders, half-baked ideas, and the beginnings of larger projects. When I’m preparing for the day, those items can mostly be ignored until I’m ready to do a review or real processing. But often, I’ll also throw in one-off tasks that need to get done quickly and don’t warrant me taking the time to add them to a project or assign tags. Since these will never leave my Inbox, it’s important to me to do a quick catch-up of what’s in there, or they might get lost among the chaos of my more organized projects.

Here’s the first version of the Inbox shortcut I built. It’s a basic example of how to query for tasks.

(Quick note: I originally wanted to call this shortcut “What’s in my inbox?” as that’s the most natural phrase for me to speak. But I use all of these shortcuts hands-free while driving with CarPlay. And since iOS assumes you’re asking about Mail.app because of the word “inbox”, it complains that you aren’t allowed to use Mail.app while driving. So, I have to add the “tasks” qualifier to make the system run my shortcut.)

Here it is in action:

This works well enough, but it can be improved. Because Siri is just reading the raw output from the OmniFocus query, it’s too difficult to discern the separate tasks she’s speaking. It doesn’t sound like natural speech.

After a little bit of experimentation, here’s a better example that I can run by asking, “Hey, Siri. What’s due today?”

Siri is easier to understand in this example because I’m sending each task to voice one at a time and a one-second pause between each.

Let’s take things one step further and ask for a rundown of the upcoming week – including an overall summary as well as dates for each task.

It takes 23 actions to piece together that Shortcut. But I think the results are worth it.

I construct my OmniFocus query and then loop over all the tasks – formatting each one into a sentence – and combine them into a single, larger string that I send to voice output.

Using simple punctuation and putting a newline between each task forces Siri to speak the results more naturally.

So, that’s how I talk to OmniFocus.

With a few custom shortcuts as well as Voxmail and CarPlay’s built-in calendar support, I’m able to get an excellent overview of my day on the drive into work. I can triage emails, find out what’s due on my task list, and hear any new meetings added to my schedule overnight.

It lets me use my otherwise dead time commuting to prepare for the day and feel more confident when I dial-in to my morning call.

A good friend texted me the other day. They said:

I’m jealous of a lot of your work ethic, but the fact that you enjoy writing is the biggest one I think

I don’t share that to say that my work ethic is better than anyone else. I’ve been called “lazy” my whole life by teachers, friends, even loved ones when it comes to me not putting effort into things I’m not passionate about.

Is that a personal flaw? Yes, I think so. If I could have mustered the maturity and self-discipline to study for the classes I wasn’t interested in, I probably wouldn’t have flunked second-semester college Biology two times. I probably would have remained in past jobs longer. And a million other screwups and failures throughout my ridiculously privileged life could have been avoided if I had just cared enough to try harder at the things I didn’t care for.

A few years ago, my therapist told me I’m going to have just the right personality and temperament to enjoy my 40s when I get there. I wasn’t entirely sure how to take his comment then, but now that I’m well into my thirty-eighth trip around the Sun, I think it’s beginning to sink in.

What I mean is, I feel like I’m dangerously close to discovering the cheat code for my own life. After a decade of turbulence, I’m more at peace with myself than I ever have been. Thirty-eight years into being here, I finally understand myself well enough to forgive my shortcomings (while continuing to try and be better) and realize what makes me tick, what motivates me, and how I can fight back against the worst parts of myself and stay healthy.

Everything above is just a long-winded and meandering introduction to say that this post is about motivation. Specifically, the two most significant motivating factors that contribute to my “work ethic,” as my friend said.

Jerry Seinfeld

The first one is so dumb and straightforward that I can hardly believe it works. I didn’t even realize I was using it to my advantage until I stumbled upon a story about Jerry Seinfeld that accidentally made the idea internet-chic.

There are a million blog posts and articles explaining it, so I won’t bore you with a detailed rehashing. But, in summary, do the thing you want to do every day. The more days you can muster in a row, the more leverage you create to keep yourself from ending the streak – from breaking the chain.

I’m tempted to dismiss the whole idea as nothing more than a fancy way to build a habit, except that I think the insight of using an ever-growing streak – compounding interest, essentially – as leverage against yourself can help you through the period before it becomes a habit. At least that’s how it has helped me.

Two quick examples.

For a long time, I kept a daily journal using the wonderful Day One app for Mac and iOS. Whether added for this reason or not, I don’t know, but the main screen displayed the number of consecutive days you last wrote an entry. I accidentally got my streak up to twenty days or so and just never wanted to see that number stop climbing.

Soon I had a couple of months in a row, and by the time I finally let a day lapse without writing, over two years had passed.

Along those lines, when it comes to the software I write, I really do enjoy looking at my GitHub contribution chart. And while I think it’s a complete asshole move to judge anyone else by what theirs looks like, I like seeing mine.

While maybe not as specific or as motivating as a number you can count, it’s fascinating to see the relative ebbs and flows chronologically. I can often correlate the chart seasonally or to my mood levels over time. And, yes, it gives me a bit of an endorphin rush when I can look back and feel proud of what I accomplished.

I’ll end this section with a recent quote from one of my very favorite people, Kourosh Dini.

Moving something forward a little bit each day is likely more important than doing something all at once. Doing so helps you to build the structures needed to keep moving forward.

I wrote something similar (but not nearly as eloquent) six years ago.

Moving on.

Fear

The other big thing that pushes me forward is fear.

When I stay busy, productive, engaged, curious, whatever you want to call it, I feel mentally healthier. That doesn’t mean I work all the time or that I don’t binge-watch a season of TV every now and then, but without some baseline level of gears turning in my head, solving problems, and learning something new, I get dangerously bored – for lack of a better word.

I turn inward. I shut down. I’ve been to some very dark places in my life, and in hindsight, the warning signs were always there. Chief among them is losing interest in the work I am passionate about.

And so I’m incredibly fearful of that happening again. Call it a precursor or a canary in a coal mine, but if I can gauge my ability to remain engaged in my work as a barometer for my mental health, I’m happy to do so.

Kourosh’s post I linked above offers this quote from Paul Tillich‘s The Courage to Be.

Courage can meet every object of fear, because it is an object and makes participation possible. Courage can take the fear produced by a definite object into itself, because this object, however frightful it may be, has a side with which it participates in us and we in it.

If I’m going to be afraid, I’d much prefer to use that emotion to my advantage, stay busy, and build things that make me (and hopefully other people) happy.