442: ‘Bad Dates’, With Jason Snell

I’ve been trying to get you on for weeks, finally did, and in the meantime I got mad at you—so let’s clear the air before we see each other next week.

I loved your Upgrade recap of the Apple Report Card, especially the bit about keeping categories tight, but you lost me when you floated an A for the Mac and waved off the Tahoe blowback.

Peace offering first: you were right about a Siri and AI category, and I’m adding it next year.

On Tahoe, I agree the design stumbles are real—icons in menus, liquid glass overreach, inconsistent touches—but the functionality is the best in years, and Mac hardware is a near‑perfect anchor.

I pushed to a five to be a rascal, not because it’s flawless; I use it daily and find it ugly in spots yet productive, with system automation triggers, a meaningfully better Spotlight, and built‑in clipboard history.

I was literally going to ask what launcher you use; you beat me to it.

I’ll admit I also said it knowing you’d hear it, which made it extra fun.

The corner‑resize fiasco made me nuts—sometimes you slam the cursor into a corner and it works, sometimes it’s nowhere; a dev even mapped the hotspot to prove it was broken.

Apple seemed to fix the hit area in the release candidate, then reverted, likely because some apps stash controls in corners; it’s a tiny sign they’re listening, but the rounded‑rect windows still feel off.

Yep—it’s a mess design‑wise, and the icons are pure noise; it screams information architecture drift and a culture where usability advocates lose the argument.

This goes back to Jobs; he had taste and spoke the language of human‑computer interaction, like making the key window obvious, while today’s pitch feels like graphic gloss without the fundamentals.

Tim doesn’t have that bone, so he relies on lieutenants; if you back the wrong compass, form wins over function, or designers assume engineers will magically fix legibility later.

When HI stopped reporting through software engineering, the craft lost its check‑and‑balance; style can live with industrial design, but interaction rules should sit with engineering.

Post‑Jobs, Apple elevated Jony to steady the markets; I think he tired of gadgets and the software fell to his bench.

I’m not saying everything under Alan Dye was bad—Dynamic Island was brilliant—but he played politics well upward while many designers below were miserable; his exit exposed that gap, and I’m hopeful about Stephen Lemay.

He may also have wanted a bigger chair or different reporting line, or just chased a huge offer; motivations can be surprisingly simple.

The panel flunked Apple’s impact on the world, and I get it; when you hand out a gold trophy with an Apple logo in this political climate, the vibes bleed into other grades.

That category mirrors the room; some argued pragmatism about tariffs, others said, what’s the point of FU money if you never use it, and the halo that Apple cared about bigger ideals felt gone this year.

Apple still honors MLK on the homepage and hasn’t done the culture‑war pivot others embraced, but no one gave them credit because of earlier choices that soured the mood.

I suspect they learned that saying no brings pain, so now they over‑attend; not an endorsement, just reading incentives in an ugly era.

Back to Tahoe: I’m staying on Sequoia because I already have great tools—LaunchBar, long‑lived clipboard histories, all the nerd gear—and those menu icons wreck readability for me.

I forced myself to live with Spotlight and Apple’s clipboard for the review and never went back; I remapped a key, miss LaunchBar’s drag‑to‑app trick, but Spotlight is finally strong and LaunchBar had become flaky here.

The new automation triggers plus cloud models in Shortcuts are fantastic; I auto‑generate alt text and filenames for images, though Shortcuts still fails silently too often.

Clipboard history is a safety net, not a luxury; I use Pastebot with sync and Keyboard Maestro filters, and I want more retention than Apple offers.

Sherlocking is fine—platforms should ship the basics—while third‑party apps own the edges with power features Apple will never touch.

Ideas are cheap; execution wins, which is why BBEdit thrives despite TextEdit, and why I’m thrilled automation and AppleScript survived even as Messages moved to a new framework.

I still rack up small wins like auto‑converting WebP to JPEG on the desktop with a four‑step Shortcut; time and file‑event triggers feel like the Mac finally remembered power users.

Creator Studio is a mess of App Store plumbing and confusing SKUs; even Apple couldn’t merge listings cleanly, and the old apps now nag you at launch.

That alone says a lot about the App Store; value‑wise, Final Cut and Logic on Mac and iPad for a subscription is solid, but shoving iWork into that bundle with upsells is what set me off.

Seeing premium assets pushed in Pages and Keynote cheapens what used to be table‑stakes apps that came free with the Mac.

Those are everyday tools, not just for ‘creators’; if Apple wants to sell paid assets, make a modest plan for that instead of freemium‑izing the defaults.

Apple long told developers not to do bundles and upsells, and now it’s bolting those tactics onto its own apps in ways that feel lousy for users.

Call it a little schadenfreude, but the bigger point is this: some tools belong in the system, and iWork has always been part of making a new Mac feel complete right out of the box.

Think of a premium hotel balancing profit and promise; if you start charging for the basics, you chip away at the brand, and that’s exactly what freemium nudges inside iWork do.

It’s like checking into a four‑star room and finding bottled water costs extra; nickel‑and‑diming the essentials ruins the vibe.

A minibar upsell is fine because it’s optional, but inserting upgrade nags into core editing flows turns something that should be nice into something noisy.

Making better Keynote templates and smart spreadsheet fill‑ins a paid perk signals that free improvements may be over unless you buy Creator Studio, which clashes with why iWork exists.

Even if one feature leans on AI, it’s table‑stakes stuff, and putting a toll booth on basic spreadsheet behavior feels cheap.

For next week’s “experience,” I’m expecting a staggered rollout: iPhone on Monday, iPads on Tuesday, and Mac press releases Wednesday morning with Air and Pro chip bumps plus that rumored low‑cost MacBook.

They often drop news at 6 a.m. Pacific, and the earlier New York start also syncs with simultaneous London and Shanghai sessions.

We’ve even done New York events where everyone watched a video first, so a day‑by‑day, product‑line cadence still makes the most sense.

Displays could slot in if ready, but odds favor saving a new Studio Display or XDR for a later Mac Studio moment rather than overstuff this week.

I could see them keeping monitors separate anyway; refreshing nearly the whole laptop lineup is plenty on its own.

I’m genuinely excited about the low‑cost MacBook, because Apple Silicon finally lets them hit a lower price without dropping below Apple’s quality bar.

People freak out when a chip doesn’t start with M, but A‑series parts have been fast enough for laptops for years, as the Walmart M1 Air sell‑through showed.

Benchmarks suggest an A18 Pro beats M1 in single‑core and keeps pace elsewhere, and that’s what most folks feel when they browse or use one app at a time.

My bet is a $799 list price with quick street discounts to around $699, maybe a single RAM option with paid storage bumps, and initial headlines screaming it’s too high before reality settles in.

Set it a bit higher, leave room for education and retail specials, and you’ve got a durable price story.

Name wise, I think they just call it MacBook, make it surprisingly thin, and give it colors that even tempt Air owners who wanted something more fun.

That mirrors the low‑end iPad strategy—compromises where they don’t hurt, plus playful finishes that speak to students and families.

A laptop is a bigger, more personal purchase than a base iPhone, so delight matters; I still hope the E phones get at least one bold color too.

Offer both muted and bright options and let the market decide; after decades of gray, the idea of a green Mac out in the wild is just plain fun.

I also love the yearly 16E cadence, and using a current A‑series in a budget MacBook keeps Wi‑Fi, Bluetooth, and everything else modern without leaning on five‑year‑old guts.

Apple can hold the chassis for years, swap in new A‑series chips as they roll, and keep margins healthy while the product stays fresh.

New anodized colors every year wouldn’t hurt either; and on that cheerful note, thanks for coming back—truce achieved, no punches next week—and thanks to Squarespace, Sentry, and Notion, and to everyone following along at Six Colors and on Jason’s shows at Relay FM and The Incomparable.