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.

Home Screens: Kourosh Dini

This week I’m featuring the Home Screen of my friend, Kourosh Dini. Kourosh has written several excellent books and, in addition to being a doctor, is one of the most mindful people I know. And now Kourosh has a podcast, Rhythms of Focus – for Wandering Minds, ADHD, and Beyond. This was an instant subscribe for me.

So Kourosh, show us your home screen.

What feature are you using most now?

Seeing someone dictate a message to themselves with an old-school handheld tape recorder tickles me.

To this end, I’ve set my phone’s action button to trigger the shortcut “Dictate to Drafts”. An idea appears, I press the button, and talk. When done, Drafts acts as a way station to send the text to either OmniFocus as tasks or to DEVONthink To Go as ideas for future development.

What’s on your Lock screen?

The lock screen has a few noteworthy items. Buttons include:

  • my OmniFocus Inbox (currently holding 2 unprocessed items)
  • my OmniFocus “Currents” perspective, showing me the main things I’d like to visit today.
  • BusyCal showing me the time of my next appointment
  • the temperature

The bottom right has a quick entry button for OmniFocus.

What are some of your favorite apps?

Most of what’s important to me is jammed onto the front screen and in folders:

Main

  • 1Password is still my goto app for handling all my passwords
  • BusyCal has an excellent two week view on MacOS. The iOS version syncs nicely.
  • DEVONthink To Go lines the bottom and has two short cuts to create new documents in specific folders. One is “+Note” which goes to my Inbox for general notes and ideas. The other is “+Journal” which automagically creates a note with its title being today’s date and time. The note is created in a dedicated Journal group in DEVONthink. The shortcut opens the file where I can start writing.
  • OmniFocus (see below) has the privileged position of the bottom right corner. A long press gives me access to the Inbox, Quick Open, and Quick Entry. But I don’t use the long press feature. Odd.

Time and Health

  • Due is just a solid app for managing time-based alerts. I absolutely love the auto-snooze feature. It makes a gentle ding, waits 5 minutes, and dings again, continuing until I tell it to stop. This totally removes the problem where an alert goes off, and I have to debate, “Do I drop this thing I’m doing and leave it a mess? Or do I wrap things up, hoping I’ll remember to do the other thing? Or do I leave the alarm blaring at me?” With this system, I can take my time making the decision, and either wrap up or continue what I’m doing without forgetting either.
  • Simple Timer (for meditation) – Meditation has always been simple for me. Give me a nice meditation bench and a no-fuss timer, and I’m happy.
  • Yoga is a subscription app with a great teacher and a continually shifting set of poses every day. Between meditation and yoga in the mornings, I feel quite solid and refreshed for the day.

Work

  • Square and Square Invoices – I like making money. This makes me money.
  • epocrates – Great app for knowing the dosing and conflicts involved with medications I prescribe or take.

Listen

  • Audible – I’m very late to the game here. Usually I read the old fashioned way with paper and eyeballs. I’ve only recently tried listening to an audiobook. I’ve just wrapped up the first book in the Dungeon Crawler Carl series as recommended to me by a neighbor. It was fun, like a radio play!
  • Music – Apple presents nice recommendations based on what I listen to. It’s easy to get to my tracks and I like reviewing my history of what I’ve added over the years.
  • Podcasts – I don’t listen to too many. But I’m now making one: Rhythms of Focus. You should totally listen. It’ll blow your mind.
  • myNoise – very nice for making a whole series of noises. I like mixing rain and white noise

Communications

  • Spark – solid email client
  • Sanebox – it took me forever to give this one a try, but I find it super useful to cut down the email noise.
  • Reddit (see below)
  • Instagram
  • Circle – my app and hosting site for my Waves of Focus course for Wandering Minds, ADHD, and Beyond.

Study

Music & Video

  • Spire – connects to my Spire Studio which is great for recording guitar noodling in the living room
  • Sidus Link – controls the lights in my recording studio as I perform at the piano.

Create

Which app is your guilty pleasure?

Still Reddit. Though more recently Instagram.

I’ve always had an aversion to social media, starting with MySpace, then Facebook, and beyond. But in order to market, I’ve needed to learn about this whole internet thing, which seems to have taken the shape of funny videos interspersed with doom. So, I add to the cacophony.

But Reddit seems to have deeper conversations, whether its about r/ADHD or r/Ravenswatch. While there is certainly a fair share of nonsense, there are also a lot of thoughtful, helpful, and fun discussions to browse through.

What app makes you most productive?

OmniFocus continues to be my productivity app of choice. It has consistently housed my projects and tasks since its inception in 2008. I’ll periodically explore other options, but OmniFocus remains the stalwart choice. Every time I try something else, as pretty or interesting as they might be, I inevitably run into, “it doesn’t do what?!” and I’m happily back in the arms of my beloved.

The only other compliment, not even competitor, is pen and paper. I’ll use it to “anchor” myself when feeling scattered or looking to stabilize myself against a tendency to run off on rabbit trails.

I’d love to write a next edition of Creating Flow with OmniFocus, but there’s only so much time in the day. The project sits there, a dormant seed awaiting the light of attention.

What app do you know you’re underutilizing?

Perplexity. The more I practice using AI, the more I realize how useful it can be.

I understand how afraid people can be of it. Will we lose our jobs? Will it become our bosses? Will it consume us?

Frankly, I don’t know. I’m more afraid that, as a group, humanity has an unwarranted faith in technology. “Hey, let’s put the AI in charge of [whatever]!” Yeah, maybe.

Playing with AI though, it seems much better suited to enhancing what a human has put together than creating things de novo. I’ll first write my newsletter on my own. Then I’ll ask Perplexity for help with readability, headings, tags, and the like. Sometimes, it will even point out something I’d written in the past, and I’ll say, “oh yeah!”

When I’d first approached it, I was entertained by making it talk like Sponge Bob Squarepants. Then I acted cruel towards an AI Mario character for some sadistic reasons I’ve yet to figure out about myself. (Probably something to do with competitive mustache feelings.)

But then I actually started to use it for my newsletters. At first, it annoyed me as the AI was wrong in just about everything. It didn’t sound like what I’d write. It didn’t research what I wanted. Its suggestions for my audience were generic at best.

But when I started to have conversations with it, noting the problems, feeding it my own writings as examples and more, it actually became useful. I started to ask it what it needed from me to be more useful. In other words, I started to develop a relationship with it.

I haven’t figured out how we can skip along the lakeshore at sunset together yet. But that’s probably for the best.

I really liked your recent post on using it on the iPhone.

Do you have an Apple Watch?

Nope. I tried an analog watch for a bit. Then didn’t. I prefer to reject clock time whenever possible, in favor of self time.

What’s your wallpaper and why?

I took a picture of a hibiscus flower that my wife has been growing. A flower shows up to bloom only for a day or two, then fades. Then another flower appears. It’s lovely.

Thanks Kourosh!