Why Dictation is Easier and More Relevant

I’ve been talking to my computer for decades, and it’s finally paying off for everyone.

Yesterday I dictated this entire newsletter into my iPad mini using the Drafts app and WhisperMemos while sitting in my backyard. No special microphone, no training sessions, no leaving awkward pauses between words like I had to do in the old days.

Just hit the red button and start talking. The fact that this works still amazes me.

The Long Road to Here

My dictation journey started with Dragon Dictate, back before it became Dragon NaturallySpeaking. You had to… leave… spaces… between… each… word… or… it… didn’t… work.

Even when I got pretty skilled at it, every document needed serious cleanup afterward. The software had no context, so “their” and “there” were constant battles, and forget about getting proper names right, even with extensive training.

For years, dictation felt like a promising technology that never quite delivered on its promise. You needed professional microphones, quiet rooms, and the patience of a saint. Most people tried it once and gave up.

But something fundamental has changed. The AI models powering today’s dictation tools understand context in ways the old systems never could. They don’t need training on your voice, they handle background noise gracefully, and they make intelligent guesses about what you actually meant to say. It’s the difference between a computer transcribing sounds and an AI re-constructing speech.

There are so many good Whisper-based apps available now. The real breakthrough isn’t any single app, it’s that we’ve crossed a threshold where dictation just works.

The hardware requirements have disappeared, too. I’m dictating this on an iPad mini using its built-in microphone. No headset, no external mic, no special setup. Because I’m outside right now, there birds chirping and a trash truck drove down the street a few minutes ago. It doesn’t matter. The same device that’s perfectly fine for FaceTime calls turns out to be perfectly fine for dictation.

How It Changes Your Writing

Thinking verbally is different from thinking with your fingers or a pencil. When I dictate, I err on the side of abundance in my first draft, then edit ruthlessly. It’s perfect for my natural workflow.

There’s something about speaking your thoughts that makes the writing more personal. When I’m typing or writing by hand, I tend to edit myself before the words hit the page. With dictation, ideas flow more freely. I’m more willing to explore tangents and follow interesting threads. You can always clean it up later.

Part of me still thinks fondly of Captain Picard doing his captain’s log on the Enterprise. That’s basically me every day now, creating content for you.

If dictation makes you nervous because your thoughts come out messy, solve that with preparation. Spend some time making a mind map or outline before you hit record. Then trust that you can fix it in the edit, and let your voice get a little more personal.

Give It Another Shot

Not everyone has delved as deeply into this rabbit hole as I have, but I’m telling you: if you tried dictation in the past and gave up, it’s worth revisiting. We can finally declare dictation a solved problem. I honestly didn’t know that would happen in my lifetime.

The tools are there, they work reliably, and they’re getting better every month. Whether it’s Apple’s built-in dictation (which is acceptable but not best-in-class), or some third-party Whisper-adjacent transcriber, pick one and give it a real try for a week.

Direct Mail: Email Marketing Without the Browser Bloat (Sponsor)

I’m happy to welcome back Direct Mail, a true Mac-native email marketing app that’s been making waves with MacSparky readers.

Most email marketing platforms live in your browser, which means you’re always one accidental tab close away from losing your work. Or you’re dealing with a sluggish interface because your internet connection decided to take a coffee break. Direct Mail takes a different approach. It’s a real Mac app that harnesses your computer’s power to work faster and more reliably than any web-based solution.

What I appreciate about Direct Mail is how it handles the details that matter. The app features over 50 mobile-optimized templates that you can customize using a drag-and-drop editor. However, it also integrates with macOS features you already use—such as Photos for images and Apple Intelligence Writing Tools for refining your copy. You receive detailed campaign analytics that show not just opens and clicks, but also individual subscriber activity and engagement patterns. And if you’re using WooCommerce, there’s now built-in integration that connects your store data directly to your campaigns.

The pricing is refreshingly straightforward. You can send up to 150 emails per month for free forever. Need more? Plans start at $20/month or you can go pay-as-you-go if subscriptions aren’t your thing.
If you’re tired of fighting with clunky web interfaces, check out Direct Mail. It’s free to download and try, and you might find that email marketing on the Mac can actually feel… good. Check it out.

This Is What Happens When You Listen to Too Much Jazz (McSweeney’s)

Too relatable for any lifelong jazz fan. A few of my favorites:

Get excited when, in the noise of the mall, you hear the perfect high-hat rhythm. Only to find that it’s coming from a coffee machine.

Feel surprised when you see a photograph of musicians that’s in color.

Start using phrases like “Dig it!” or “Solid, man!”

A young barista with a nose ring notices your T-shirt with Satchmo’s picture—trumpet to his lips, eyes wide. When she smiles and says, “I love jazz. I saw Michael Bublé in concert,” you scream, “Bublé is not a jazz musician—he’s a lounge singer!” …

Ternus as Next Apple CEO?

For years, I’ve been watching John Ternus at Apple events and thought he just carried himself like an Apple CEO. Rumors are increasingly pointing toward him as Tim Cook’s successor. In my mind, this fits for a few reasons:

  • I think the next CEO will be someone already inside Apple.
  • I think the next CEO will need to be a younger generation than the existing senior management.
  • It needs to someone who can handle himself as the CEO of one of world largest companies, like John Ternus.

Apple has a deep bench. I’ve met lots of Apple executives over the years, dripping in competence. But John Turnus is the only one they seem to find a reason to put in front of the public at every chance. I’ll be surprised if, when Tim Cook decides to step down, it’s not Ternus.

The 2026 Focused Calendar

I’m pleased to announce that the Focused Wall Calendar for 2026 is now on sale. Mike and I have been collaborating with the NeuYear folks for years, and this is, in my opinion, the best wall calendar on the market.

We’ve spent a lot of time tweaking this calendar over the years to get it just right. Here are some of the features I love:

  • It starts on Monday, as a proper calendar should.
  • It’s big at 25 inches by 36 inches. This isn’t one of those calendars you have to squint at.
  • The year-at-a-glance view is invaluable. Over the years, this calendar on my wall has gotten me out of a lot of pickles as I look at the calendar to see just how busy I am before I say yes to another commitment. There’s something about seeing three weeks of wall-to-wall appointments that makes saying no much easier.
  • It’s designed with no gaps between the months. The philosophy is simple: we think in weeks, not months. This calendar presents 52 weeks as a continuous flow, which makes it easy to see the distance between any two dates and plan across months without artificial boundaries.
  • You can write on it with dry-erase or wet-erase markers. I’ve tried both, and they both work great. The dry-erase is better if you’re constantly adjusting things, while wet-erase stays put better for long-term commitments.
  • It’s two calendars in one. Flip it over and you get a different orientation. One side is portrait, the other landscape. I keep mine in landscape above my desk, but you can hang it vertically on a door if that works better for your space.
  • The quarterly shading is genius. The calendar breaks the year into four quarters with background shading, making it easy to set quarterly goals and see reset points throughout the year. Buffer weeks are built in so you can review what worked, celebrate wins, and adjust course if needed.
  • The habit tracking system at the bottom lets you create your own color-coded system. Each day has space to track up to four habits, and it shows you how many days are left in the quarter to keep you honest.

It’s beautiful. This matters more than you might think. When your productivity tool looks good, you actually want to use it. Attraction breeds commitment.

You can buy it now. Mine is already on order.

OmniOutliner 6 Now Available on TestFlight

I still remember walking into a Micro Center store sometime in the early 2000s and getting drawn to the OmniOutliner box. Back then, you bought software in a box, and this box was gorgeous with screenshots of what we would later call a Mac-assed Mac app—clearly built to squeeze all the juice out of your Mac. I was intrigued by the idea of a dedicated outlining app.

I took it home and that purchase started a relationship with The Omni Group that continues to this day. Their commitment to building thoughtful, powerful tools for Mac users has kept me as a customer for over two decades. So when I heard OmniOutliner 6 was coming, I paid attention.

What’s New in OmniOutliner 6

The Omni Group is making OmniOutliner 6 a universal app with feature parity across Mac, iPhone, iPad, and even Apple Vision Pro. That means the iPhone and iPad versions can now handle advanced filtering like the Mac version, and the Mac app gets a cleaner workspace with the ability to hide the bottom bar. 

Omni Links is one of the standout additions. You can now link to local and remote documents across multiple devices, plus regular web links. It works with iCloud Drive, Dropbox, Google Drive, Google Docs, and local servers through user-defined “Connected Folders.” The goal is simple: links that just work, wherever your files live.

There’s also a new AI Tools feature that leverages Omni Automation plugins and Apple’s on-device AI model. You can pull information from emails, web pages, documents, or your clipboard, turn it into outlines, and export those outlines however you need: Keynote presentations, blog posts, Obsidian entries, you name it. It’s highly customizable and practical.

OmniOutliner 6 includes plenty of other improvements: an enhanced dark mode, multiple windows on Mac (even for the same project, so you can drag content between them), shareable custom styles, resizable inline attachments, and full AppleScript support.

Try It Today

The Omni Group has opened up TestFlight access for OmniOutliner 6, but spots are limited. If you’re curious about where outlining tools are headed, join the TestFlight here. You can also check out the full release notes if you want all the technical details. I’m looking forward to putting OmniOutliner 6 through its paces. For anyone who relies on outlining in their workflow, this is a significant upgrade.