Focused 247: Getting Intentional, with Chris Bailey

Chris Bailey is back on this episode of Focused to talk about his new book The Intention Stack, fundamental human values, and why S.M.A.R.T. goals aren’t very smart.

This episode of Focused is sponsored by:

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Gemini and Siri

We’ve now got official confirmation that Apple and Google are working together on what I’ve been calling the “Siri brain transplant.” Instead of an Apple LLM technology, it appears they’ll be using some version of Gemini. There are many unanswered questions here.

For instance, is the Gemini-based model going to be both local and in Apple’s Private Cloud Compute space? I like the idea of a Gemini-caliber PCC engine I can access privately from my Apple devices.

The original sin here isn’t Apple’s failure to build its own LLM over the last few years, but rather its lack of attention toward Siri throughout its lifespan. Anybody who cares about this stuff has experienced frustration as Siri never evolved the way it should have. Indeed, Siri has been the butt of popular culture jokes for at least a decade.

I’ll always believe that if Apple made Siri a priority ten years ago, they wouldn’t be in this position today.

Nevertheless, all of this feels more like a black eye than a knockout. There is still time for Apple to evolve and we’re all still figuring out what LLM-based AI means for all of us.

If I were going to look for a silver lining on this, at least Apple had the maturity to swallow their pride and go get help.

But let’s not forget this is all still just news. I still haven’t seen Siri work the way I’d have expected in 2026.

Timing: Time Tracking That Does the Work for You (Sponsor)

Today’s sponsor is Timing. If you’ve got “understand where my time actually goes” on your 2026 goals list, this is the app that can make it happen.

Most of us know we should track our time. Knowing how you spend your hours is the first step to spending them better. But manual time tracking is a pain. You start a timer, get interrupted, forget to switch it, and by 3 PM, your log looks like fiction. The friction kills the habit before it takes root.

Timing takes a different approach. It runs quietly in the background on your Mac, watching which apps you use, which documents you open, and which websites you visit. Then it categorizes everything automatically based on rules you define. Work in Scrivener for two hours? That’s writing time. Spend 45 minutes in Safari on research? You decide once, and Timing remembers.

What’s new is the AI summaries feature. Timing now analyzes your work and automatically groups related activities, highlighting the key topics you’ve worked on. Instead of scrolling through a raw timeline, you get an instant understanding of how your day actually went.

The app also tracks beyond your Mac. It imports Screen Time data from your iPhone and iPad, so you see your complete picture across devices. It even detects when video calls end and prompts you to log that meeting time. For anyone doing client work, this eliminates the anxiety of wondering whether you’ve captured everything accurately.

Timing is a native Mac app. Not an Electron wrapper or a web app pretending to be desktop software. It’s fast, it respects your privacy by keeping data local (unless you opt into sync), and it feels right at home on macOS. Plans start at $9/month for Professional, with Expert ($11/month) adding AI summaries and Screen Time integration, and Connect ($16/month) for team features. All plans come with a 30-day free trial.

January is the perfect time to start building this habit. Check out Timing and see exactly where your year is going.

Five New Apple Products in 2026? Yes, Please.

If the rumors are true, 2026 is shaping up to be one of Apple’s most interesting hardware years in recent memory.

According to the rumor mill, Apple has five all-new products in the pipeline: a foldable iPhone, augmented reality glasses, a HomePod with a touchscreen, home security cameras and a video doorbell, and a more affordable MacBook. That’s a lot of new territory for our favorite fruit company.

I’m genuinely optimistic about all of it.

The iPhone Fold

It’s time. I have several friends who love their Android folding phones, and I’ve watched them unfold those big screens with some envy. Apple’s late to this party, but that’s never stopped them before.

The interesting thing is that this likely creates a new kind of trade-off at the top of the iPhone lineup. I expect the iPhone Pro will still have the better camera and longer battery life.

So for the first time, there won’t be a single “best” iPhone. You’ll have to choose: big folding screen or superior camera and battery. That’s a healthy problem to have. Either way, I’m curious to see Apple’s take on a folding phone.

Augmented Reality Glasses

I expect Apple’s first steps here will be tentative. The Meta Ray-Bans have proven there’s a market for smart glasses that don’t look ridiculous.

Apple has a history of entering existing product categories and making something genuinely great. The Vision Pro showed they’re serious about spatial computing.

Lightweight AR glasses feel like the natural next step. Let’s hope they can pull it off.

HomePod with Touchscreen

This one has been rumored for years, and I’ll admit I’m strangely invested in it. I love the idea of dedicated home control centers. If Apple takes it in that direction, a HomePod with a screen could finally make the smart home feel cohesive instead of cobbled together.

The current HomePod is a good speaker with Siri bolted on. A touchscreen version could be something much more useful.

Home Security Cameras and Video Doorbell

This one is overdue. I’d love to see Apple get serious about HomeKit hardware.

Right now, finding home security products you can truly trust with your data is harder than it should be. Apple’s privacy-first approach could be a real differentiator here.

I’m not expecting them to out-feature Ring or Nest on day one, but if they nail the basics with solid Apple integration and strong privacy protections, I’m interested.

Affordable MacBook

Finally. Apple Silicon is so good that even a basic entry-level chip would make for a genuinely capable computer.

There are a lot of people who need a Mac for school, for basic work, for browsing the web. They don’t need an M4 Pro.

An affordable MacBook with an efficient Apple Silicon chip would serve them well and bring more people into the Mac ecosystem. I sincerely hope this one comes to life.

Will They Actually Ship?

Five new product categories in a single year is ambitious. Will Apple actually ship all of them in 2026? Maybe not.

But even if we get three or four, it’s going to be a fun year to be an Apple nerd.