How I’m Experimenting with Automation (Spring 2022)

Back in the summer of 2018, I talked about how I was going to dedicate more time to automation. Since then, I’ve automated significant parts of my business, including guest outreach and booking, project creation, and even workspace configuration.

Now that Shortcuts has reasonably good Mac support, and I have an Apple Silicon Mac, I’m re-evaluating my automation strategy and exploring what more I can do with these tools.

Automations I’m Working On

There are currently a few things I’m working on that I think solve interesting problems…a lot more advanced that just connecting Thing 1 to Thing 2.

My “New Trip” Shortcut

Recently I completed a revamp of my travel automation, swapping out Omnifocus for my new task manager, Todoist…though truth be told, Omnifocus is a much better steward to the Apple platform.

The old one would ask for a name and a number of days, then calculate when I needed to order a plane ticket and create some tasks that I do for every travel event. The new one asks for a name, start date, and end date. This allows me a bit more flexibility. Plus, Shortcuts makes it easy to calculate the number of days between 2 days.

I also added 3 new actions:

  1. Create a calendar entry for the event…which isn’t something I remember to do right away.
  2. Create a Craft note in my “Travel” folder for the event.
  3. Run my Packing List shortcut, passing the number of days

These are massive improvements that let me overlook one very annoying shortcoming of Todoist: I can’t use Shortcuts to create subtasks, projects, sections, or labels. In other words, it’s easy to get tasks in, but it’s not easy to organize them…which is frustrating.

Figuring Out How to Send Data From Zapier to Shortcuts

One of the biggest hurdles for me is that my notes app, Craft, doesn’t support Zapier. Because of that, I can’t use it for everything just yet. Instead, I’ve been using Evernote for my newsletter, and Notion for my Podcast Guest notes.

I’d love to change that and I have some thoughts on how to do it. There are 3rd party apps for Shortcuts, like Pushcut, which runs a server your shortcuts can access, Scriptable, which allows for JavaScript on iOS, and Data Jar, which acts as a database for Shortcuts.

I’m hoping with this combination of stuff, I’ll be able to automatically push information to Craft….or at the very least, make that data retrievable with a Shortcut. Doing a daily data dump is better than nothing.

More Workspace Experiments

Shockingly, I just learned that Moom allows for saving window configurations. So I’ll be working more with them to make better workspaces for specific projects.

I’m also going to check out more tools for making recording better, like Bunch, which is text-file automation.

And naturally, I’ll be tinkering with my Stream Deck throughout all of this.

Interested in Watching Me Experiment?

I like working in the open and thinking through problems like this. Currently, there are two ways to see how I work through this stuff:

  1. I live stream weekly on YouTube. Join my mailing list to get notified when I’m going live, or subscribe to my YouTube channel.
  2. Those live streams are only available while they are live. If you want access to the archive, and other experiments, you can join my membership. It’s $50/year and I put out content weekly.

What are you trying to automate? Let me know in the comments!


Is it Time for me to Ditch Ulysses?

Over the last week or so I’ve been experimenting with Craft for writing. Scripts, Twitter threads, podcast episodes, and blog posts have all made their way into a new space I created explicitly for writing.

Syncing Feeling

Part of the reason is because I’m experiencing iCloud syncing issues with Ulysses every few months, and the thing they recommend, log out of all devices and log back in, is something I very-much don’t want to do.

I haven’t done a lot of recon on this, but it could be when I add or upgrade a new device…which I do too frequently to fix repeatedly.


The other reason for me possibly ditching Ulysses is consolidation. I do all of my other note taking and idea capture in Craft. I even write scripts for WP Review and sponsor reads there already, since all of my other planning documentation is in Craft.

So using Craft to write would eliminate one app from my content creation process. And while I’m doing a live stream this Wednesday (January 24, 2022) on trying Obsidian, I’m not confident I’ll make the switch.

This isn’t the first time I’m trying Obsidian, and I’m not sure it’s for me. But the live stream is an excuse to dedicate an hour to giving it a go.

Craft X

The final reason I’m considering Craft for this task is that they’re rolling out Obsidian-like extensions in a program called Craft X. So while Craft is a great iOS and Mac app, the X program will hopefully make it a good overall system for writing and publishing.

Last year the rolled out a web version of the app, so this feels like a natural successor. And this program gives me hope for my wishlist in making Craft the perfect writing app.


While I’ve been happily writing in the app for a week or so now, there are a few things I’d like to see.

First and foremost, publishing directly to WordPress. I’m hopeful this will happen for 2 reasons:

  • Craft has excellent Markdown export. Right now I copy the Markdown, paste it into the WordPress editor, and I’m good to fo.
  • There are 2 Craft X extensions: Craft to Ghost and Craft to Medium. I can’t help but think WordPress is next or soon.

I’d like a keyboard shortcut to switch between spaces. I’m moving between my main space, which is my brain dump, and the writing space, which is much cleaner, frequently. A native keyboard shortcut would be swell.

Related, space-level writing settings would be fantastic. To help me determine which space I’m in, all of my writing documents use the serif styles.

Finally, I’d love to see footnote support in Markdown. Ulysses makes it super easy to add footnotes, which translate nicely in the blog posts. Seeing that in Craft would be great. Again, Craft X has a “power tools” add-on, so I suspect this can be added, or is in the works.

What do you use to write?

What are you using to write? How often do you rethink your process? Let me know in the comments!


SavvyCal vs. Calendly

A few weeks ago In my newsletter, I talked about how I’m considering switching to SavvyCal over Calendly. There are a lot of great features to like about SavvyCal, including how calendar overlays work, one-off links, reusable hours, and recurring time blocks based on calendar events.

Plus with teams, you can do “round robin” scheduling, allowing you to easily combine multiple people’s availability – something that while SavvyCal requires a team account for, Calendly doesn’t offer at all. But I’m not quite ready to switch yet. Here’s why.

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Why Your Contract Should Have a Project Kill Switch

A lot happened between 2019 and 2021. I launched a new service that I originally called “Ship Your Podcast” – a done-for-you Podcasting service. I’ve since folded it under the Podcast Liftoff brand. But I also started doing a lot more video work…and that was the bell of the ball when I met with people at WordCamp US 2019.

I signed on clients to both services. Contracts signed. Deposits deposited. Then the pandemic hit. Two clients completely disappeared. One seems to have completely moved on. The other came back 14 months later…

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5 Recent Purchases I’ve Been Really Happy With (May 2021)

I thought I’d start a new type of post on this blog for stuff I’ve been digging. I’m not the first to think of this concept, surely. But I feel like lately all of stuff I’ve been purchasing, I’ve been really pleased with. So every so often I’ll run a list like this. Here’s 5 purchases I’ve been really happy with for May 2021.

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Making The Most Of Your Podcast Guest Spot

A few weeks ago I wrote about how to get on someone’s podcast. Congrats! Now you have your first podcast guest spot lined up. You’re set to provide value for a ready and willing audience. But being a podcast guest is about more than just talking. While you shouldn’t be going on just to hawk your wares, you should be ready to help listeners learn more about you. Here’s how.

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How to Create a FREE Landing Page with ConvertKit

ConvertKit has recently opened up a free plan for people to build landing pages and forms so they can start building their email lists. And while usually you need to refer a friend or pay to see those subscribers and send emails, in this video, you’ll get a special link that will unlock 100 subscribers and broadcasts for free. You will also learn how to build a nice looking landing page to compel people to join your mailing list.

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Build Your Website Toolkit Cheaply on Black Friday

Black Friday, Cyber Monday, and apparently the weeks before and after, nowadays, are a great time for you to pick up TVs, Appliances, and…software? Indeed, lots of online companies offer great deals (some even lifetime) around Black Friday. This can be very good for your business. Here’s a great toolkit you can make for cheap, thanks to Black Friday deals.

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What I Learned from Asking, “How Did You Build That?”

Over the weekend, I gave a talk at WordCamp Minneapolis about the things I’ve learned from nearly 100 guests on my podcast, How I Built It. I covered useful tools and great advice, as well as some recurring themes. Here are the highlights.

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