Why the iPhone Air Might Actually Make Sense

It’s easy, as someone who writes about this stuff, to project our own preferences onto new products. And I’ll admit, I feel that pull strongly with the rumored iPhone Air.

As rumors continue to circulate about iPhone Air, a much thinner version of the iPhone that comes in at a higher price point than the entry-level model but not as powerful as the iPhone Pro, I can’t help but wonder: how big is the market for an expensive, skinny iPhone?

We’re now seeing mock-ups floating around, like this one on YouTube, as case manufacturers gear up. And yes, it’s definitely a lot thinner than the standard iPhone. But once you slap a case on it or even stick on an extra battery, you may very well end up holding something not noticeably different in hand from an iPhone Pro. Except now, it’s close to the Pro’s price without the Pro’s camera.

Maybe that’s the real inflection point: do you want a phone that’s slightly lighter, or one with a better camera? I suppose there’s a category of users who don’t take that many photos, or maybe never shoot video, and would gladly trade camera horsepower for something thinner and lighter.

The question (to which Apple should get an answer later this year) is exactly how many of those people are out there?

Some Notable Fantastical Updates: AI Event Creation and Multiple Windows

Fantastical’s initial selling point was the frictionless creation of new events. Although they’ve added many new features since then, Fantastical hasn’t lost touch with its roots.

You can now forward an email containing an event to Fantastical (email@fantastical.app) from your Flexibits account email and Fantastical’s AI will, on the back end, parse the email and add the event to your calendar. Clever.

Calendar management is one area ripe for AI assistance, and I hope this is just the beginning for Fantastical.

Another Fantastical update that has been a game changer for me is adding multiple window support for your Mac. So now I can leave my big monthly calendar as a full-screen app, while still having a movable/resizable calendar with my favorite calendar app.

The Original Workflow Team is Back with Sky

Two years ago, the original Workflow team left Apple to announce they were working on a secret project to use AI to control your Mac. Today, they revealed that product: Sky, an AI assistant you can invoke anywhere on your Mac to pull off some genuinely impressive tricks.

For those who might not remember, Ari Weinstein and Conrad Kramer were the original team behind Workflow, the automation app that Apple loved so much they acquired it and turned it into Shortcuts. If you’ve ever used Shortcuts on your iPhone, iPad, or Mac, you have these two to thank. Now they’re back with their co-founder Kim Beverett, and anything this team creates immediately has my attention.

The app isn’t available yet, but you can sign up for notifications about its release. According to their website, Sky is launching this summer, and I strongly recommend getting on that waitlist.

Sky is a Mac automation tool that integrates with any application (AppKit, SwiftUI, or Electron) and allows users to control their computer through natural language commands. Its standout feature “Skyshots” captures both visual content and underlying data when you hold both Command keys, enabling you to reference screen content with phrases like “this” or “here.” The tool excels at natural language processing for tasks like organizing files or creating calendar events from displayed data, while offering built-in integrations for Calendar, Messages, Notes, web browsing, and other core Mac functions. For advanced users, Sky supports custom tool creation through Shortcuts, AppleScript, and shell scripts.

People are already taking swings at putting an AI layer on your Mac, but I’ve yet to find an implementation that feels natural. Sky looks like it may be the one that figures that out.

The ability to just ask your Mac to do complex tasks – and have it actually work across any app – is the kind of thing we’ve been promised for years but never quite delivered. If Sky can execute on this vision (and given this team’s track record, I’m optimistic), it could fundamentally change how we interact with our Macs.

Federico Viticci’s detailed preview at MacStories goes much deeper into Sky’s capabilities and technical implementation if you want the full story. But honestly, this is one where I can easily recommend you go sign up for the waitlist. When the team that created Workflow and Shortcuts builds something new, it’s worth paying attention.

The future of Mac automation might just be as simple as asking for what you want.

On Teachers and the 2025 Productivity Academy

When I was a boy and first showed up for school, I was tested and found to be entirely … adequate. I wasn’t particularly sharp, but I was earnest. As such, I didn’t find myself in the “smart” classes with the “smart” kids.

And yet…

In those ordinary classes with the rest of the ordinary kids, I bumped into some of the most extraordinary teachers. To name just a few: Ms. Carol, Ms. Sartor, Ms. Puckett, Mr. Mercer, and Professor Peterson.

Each of those teachers saw things in me that I did not see in myself. In turn, each of them gently yet firmly put their hands on the tiller of my life, making the most subtle course corrections that, so early in my life, entirely changed me and the course of my life.

I don’t have the skill or subtlety of those magical people.

And yet…

I would still like to help. I owe it to my teachers.

So I’m announcing the second year of Productivity Academy Summer Sessions.

A Unique Opportunity for Students

Earlier this year, I released the 2025 Productivity Field Guide, which helped many find focus in a distracted world. This summer, I’m excited to announce the 2025 Productivity Academy. This exclusive program offers the Productivity Field Guide and a four-part webinar series over the summer for select high school and college students.

Why Should You Join?

In today’s hyper-connected world, staying focused has become a superpower. Distractions are everywhere, competition is fierce, and the ability to concentrate on what truly matters will set you apart in both academics and life.

But focus isn’t just about staying on task—it’s about understanding what’s important to you and what you want to achieve. This course will help you discover your “why” and give you the practical tools to build a focused, purpose-driven life.

What You’ll Get

  • The Productivity Field Guide – Learn practical strategies that actually work
  • Comprehensive PDF Book – Dive deep into the concepts with a complete guide
  • Actionable Worksheets – Apply what you learn with hands-on exercises
  • Month-Long Webinar Series – Participate in interactive sessions to reinforce your learning

What’s the Cost?

The course is free. However, I want something more valuable than money: your commitment. You must be willing to work through the material, complete the exercises, and attend the webinars. This isn’t for casual observers—only dedicated students should apply.

Why I’m Doing This

When I was your age, I struggled to find my focus. It took me decades to figure out my “why,” and once I did, my life transformed. I don’t want you to make the same mistakes I did. You can achieve that clarity much sooner, and I want to help you get there.

How to Apply

If you’re ready to take this step, send an email including:

  1. Who you are – Tell me about yourself
  2. Your goals – What do you want to achieve?
  3. Why you’re interested – What draws you to this program?

Applications are due by June 11. Recipients will be notified shortly after, and the webinar series will start later in June.