Advanced Automation: Going Beyond the Basics

This morning? Chaos. Forgot to set a Slack reminder, started coffee, inbox exploded. Automation’s supposed to fix this, but stacking shortcuts just makes new problems—calendar events firing at midnight, random notifications. Every time I “fix” something in Shortcuts, three more things break. Nobody warns you about that in the demo videos.

Layering Shortcuts for Complex Workflows

Open any of my workflows—spaghetti city. I stack shortcuts on shortcuts because the simple stuff doesn’t cut it. Supposedly you just string actions together, but if you try branching with conditions inside schedule notifications, it breaks fast. Shortcuts plus Things 3 or Google Sheets (Google’s big on daily log automation, if you believe their blog) means you’re triple-checking variable formats.

Nesting is the word—experts at Pragmatic Works call it that. It’s like adult LEGO until one tiny logic error sends a text to your boss instead of your sister. Stack too many If-Else’s and you’ll wish Apple had version control for Shortcuts. Anyone who’s done this is quietly keeping a backup doc just in case.

Scheduling and Triggers

Triggers are supposed to be simple: time, location, open an app. I set “auto-DND at the gym,” and it turns on halfway to the parking lot because Bluetooth messes with location triggers. Even pros double-check everything, like in that Let’s Talk Tech YouTube tutorial, to catch overlaps and device sleep issues.

Schedulers in Shortcuts—calendar, reminders, NFC tags—work differently on iOS and Mac, which is nuts. Sometimes a 9 a.m. workflow runs at 10:07 because the clock’s off. I started adding logs and sending myself confirmations, or just disabling anything that looks like it’ll trigger twice. Calendar integrations are great, but third-party sync can break everything. There’s never enough testing. Sometimes it feels like automation just wants to watch the world burn.

Learning from the Pros: Insights from Matthew Cassinelli

I open my shortcuts library and—honestly?—it’s a circus. Nobody’s got a perfect workflow, unless you count whatever fresh chaos Matthew Cassinelli’s cooked up this week. The guy’s basically obsessed. He’ll take Siri Shortcuts, which already feel like a gamble, and somehow turn them into actual time-saving moves. Not the fake ones people post for clicks, but real stuff that sometimes makes me wonder if I’m just lazy or missing the point.

Innovative Workflow Examples

You know what’s wild? I wasn’t even thinking about reminders, but then Cassinelli shows up with these automations that basically make my “I’ll deal with this later” excuse look like a joke. I watched him demo a shortcut that kicks off a podcast, pings a friend, and lines up a playlist—all with one tap. My hands were full of laundry and some sketchy protein bar, and suddenly I’m questioning my life choices. One second you’re just glancing at your calendar, and the next, six background routines are firing off and you’re not even sure what half of them do. Apparently, he just shuffles existing shortcut actions around—said it himself on a podcast. Why start from scratch if you can just remix?

And, okay, it bugs me a little: he refuses to organize his shortcuts the way Apple wants. No folders, just tags and labels and a bunch of duplicates. I guess it’s his way of forcing iPadOS to behave. Check out his shortcuts catalog—it’s basically a pile of “if it works, don’t mess with it until you’re forced to.” I mean, I stepped on a Lego, got a weather update, and still found time to nuke my coffee in the microwave because of one of these dumb shortcuts. I’ll take it.

Expert Sources for New Ideas

Scrolling Twitter? I can’t go five minutes without tripping over another Cassinelli shortcut leak. He’s always ahead, dropping ideas before Apple even makes them official. It’s not just tweets, either—he’s everywhere: podcasts (see the annual iPad Pros episode), newsletters, and that shortcut library that’s always weirdly current. Once, I even caught him demoing his Apple Watch routines at the gym on a livestream. That’s when I realized, wow, I’m not even trying.

But here’s the twist: just copying templates doesn’t really get you anywhere. The real gold is in the community—the comment threads, random Slack chats, those “is this even gonna work?” drafts. Suddenly, you’ve got reminders to water plants you don’t even own anymore. The real move? Steal, break, twist, see what survives when Apple flips permissions or your shortcut just vanishes at 2 a.m. (which… yeah, it happens).