Wanting to get into automation but not quite sure where to start

Here’s the deal, I love the idea of automation and I have the following apps: Alfred, Keyboard Maestro (trial), Hazel, and TextExpander. I guess part of me is a bit overwhelmed when for instance people have many different KM micros for instance they use. Should I just take things one step at a time? Base it on my own use cases? Look to see how I can use Alfred for instance and collect Keyboard Maestro stuff and use it when I have time? Should I go to the apps respected forums? Learn along with the Automators podcast with David and Rose?

I imagine I’m not the only one excited but also a bit overwhelmed.

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I’ve considered myself an “automator” for years and am familar with a couple of programming languages. The cornucopia of automation options on macOS/iOS is both beautiful and overwhelming (still). So relax, know that you’re going to get frustrated and get ready to experiment and learn! It is my favorite part of the Apple eco-system for sure.

Always remember you can burn way more time automating than you end up saving!

So, my main suggestion is to identify the 1-3 tasks you do most frequently that require the most steps. Daily or more? Yup. 10+ clicks? That’s the one. Target these first because they have the highest ROI for you. (When starting out, things will take longer so you have to invest some time on learning.)

Eventually you’ll get a feel for the “best tool for the job” (KM, Alfred, Workflow, TE, etc.) but this takes quite a while. One fundamental is where you perform the tasks you identified. Workflow is only on iOS. KM, Alfred and Hazel are macOS only. TE is text expansion only but is cross-platform (however mostly only text editors (Drafts, etc.) support it.

But don’t jump to the tool just yet. First search for "automating " and see what comes up. Hit this forum along with Automators. If you think you know what tool will end up being the one to go with, go to its website and search the forums there. They all have very active communities.

If you identify one of your tasks and post it here we can break down how we’d go about automating it. (You’ll get as many solutions as people that post.)

Good luck, know the frustration blues will visit and keep us updated!


Don’t forget you also have Automator; and Sal Saghoian’s Automation website is a great place to start with that. Keyboard Maestro works similar to Automator in that you primarily drag actions into your script.

I use all of the tools that you listed to a greater or lesser extent. Alfred takes a bit much for me to really do more than use the built in stuff and a few workflows that I downloaded (I’m just some schmuck who likes playing with his Mac, not a programmer). I use Alfred’s search capabilities every day, but that’s hardly automation. I find the other three apps fairly intuitive, but I still need to make generous use of DuckDuckGo and the publisher’s forums to do more complex things. TextExpander is probably the simplest, but also the most limited. In fact, if you just after basic expansion, you might be able to use the macOS text expansion (System Preferences/Keyboard/Text). Expansion can also be done in Alfred and Keyboard Maestro; although, I use TextExpander for it’s cross platform availability on Windows). The Hazel and Keyboard Maestro forums are very good resources. On the Hazel forums, the developer is pretty responsive.


I love TextExpander but need to look into what all I have already. I like it as it can do some formatting and fill in form fields that make some things easier such as sending an email following applying for a job.

I’ll make sure to browse each app’s forums as well.

Great point, I can keep a running list of things I’d like to automate or make easier. Then finding the best app for the job.

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And that’s exactly the type of thing that would lead you to TextExpander over the other alternatives.

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For someone just starting with automation I would look at keeping it as simple as possible in the beginning. Hazel and Textexpander would i.m.o. be easiest to learn and have a rather direct ROI.

Alfred and KM seem to be a bit more advanced when you start out, and take a little bit more work to figure out.

In automation it is always a question of investing time to save time, and in that equation investment should not outweigh savings. So in line with the comments above: anything that is a repeating activity with more that 2-3 steps I would consider a likely candidate for automation.

But, it all hangs on what’s in it for you. Do you want to automate to save yourself some time or effort? Or is it because you just like to fiddle with tech? If it is the latter, than the ratio of time spent automating vs time saved is less of a big deal.


I’ve learned to evaluate my progress when automating to see if it’s worthwhile.
Usually it’s down to if I am learning or not, as I believe that part of the time investment will be paid back later with another project.

So, if I have spent 10 minutes on something and don’t understand what I’m doing, I stop and either abandon the project or come back to it another day. If I’m learning and enjoying myself then it’s just my hobby so I can spend hours on it.

If you have a Touchbar I recommend trying BetterTouchTool - with Automator or AppleScript if daring or just the built in commands for a taster.


Think this is your best advise. I too felt overwhelmed when I started both on Mac and iOs because I was reading about all this amazing things people were doing. Which actually became a blocker.

Start by using a couple of text snippers even if only to write dates in specic format, email addresses, postal addresses, etc. Use Hazel to sort out utils bills (there’s a good thread in this forum). Use workflow app to retrieve a phone number or send a tex message. You get the point. Start with the basics and with stuff that applies TO YOU.

By doing it, you learn, get curious, learn more and evolve. Before you realise, you’ll be doing/discovering lots of nice, crazy and complex things.


Also, you might like to consider the sister Discourse forum to this one (and associated podcast), Automators.

Yes absolutely. Keep your eyes open for repetitive tasks or finding yourself thinking: there’s got to be a better way. These clues are candidates for possible automation. Of the apps you already own, I’d suggest getting started with TextExpander. It’s easy to configure, has lots of included snippets that you can use and learn from, and there are many snippet libraries available you can import. (Personally, I abandoned TE in favor of Typinator, but the advice is the same for that app as for TE.)

KeyboardMaestro is more powerful but has a steeper learning curve. You can visit their forum for lots of suggestions and macro sets you can download and install. I like Hazel but over the years I’ve owned it I rarely make new automations – maybe I’m lazy, but I think it’s because Hazel is a niche product for people who need to do a lot of repetitive tasks involving files. I do a lot of file-related tasks but they are all different. Alfred’s automation is too obscure for me to bother learning – I use the out-of-the box features and a few routines that I’ve imported over time.


… I dunno, but capturing those things you want to apply some automation to might be something you are doing repeatedly and if you want to get all meta about it might just make a perfect starting point for a bit of basic automation. :wink:

  • Where would you capture this info?
  • How would you capture it (plain text, form, text + screenshot, by voice)?
  • Where would you store it long term and how would you prioritize them, put ideas against them, track them to completion?

Written as a low horsepower automator who never went past writing of mail rules or in iOS modifying a Drafts “rule”. I’m a firm believer in one step at a time. Learn one new app at a time. (write needed qualifiers here)

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I use all of these but Keyboard Maestro (which for me is too complicated to be worth the time investment), and also Automator and AppleScript. AppleScript is a mess but frankly is the lowest level and most powerful tool and I just can’t seem to get away from it. Automator should make automation easy but it just seems to me like an unfinished project.

Alfred comes alive when you buy the powerpack. The current version of Alfred would totally eliminate my need for TextExpander, but I’ve already purchased TextExpander. If I was subscribing to it, I’d drop the subscription. Hazel is fantastic for file manipulation automation. It could be replaced with AppleScript, but only if you were crazy.

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I’d like to get into AppleScript, maybe not scripting but at least using them. Automator I’ve used a bit but could probably replace it with something like Keyboard Maestro or Hazel. I have TextExpander and use it a good amount though wanna see if it’ll help me fill out form fields. Bought the power pack for Alfred so I need to dig into those capabilities.

So currently I’m capturing those things either in Drafts 5 or a DevonThink rtf note in my database for Workflows. Figured I’d segment things to make this easy to find and experiment. I’ve been keeping log of my experiments in Ulysses, maybe make a log of other experiments within either DevonThink or Ulysses.

Here is my list so far image

I should take a look at those TE libraries to import, I have a decent amount of snippets but should either make the shortcuts better or pair down some that I don’t use.

I agree with your thoughts on Hazel, something to revisit if a needed automation involves files. I really want to dabble and get into Keyboard Maestro but I know that it can take a while to get used to it or find use cases.

I’m excited to listen to this podcast, had to put it on 1x speed as I forget how fast Rose can talk! The show notes and community should prove useful, curious when they’ll get to Hazel and other apps.

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Really appreciate this and great thoughts. Haven’t used the Workflow app all that much, do they have a community forum and such?

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That’s a new one I haven’t heard of, I’ll have to think about that.