Lately #005: Decision Makers, a Smarter Siri, and Resetting My Software Stack

Summer days are finally in full swing, featuring copious amounts of sunshine and picnics under the tree in the yard, and I'm trying to soak it all up (despite the fact triple-digit temps are incoming and I'm already sweating just thinking about it).

There's a small itch underneath all of it to get my own systems sorted before whatever's next (more on that below), but the agenda most days right now is sunshine and sandwiches, and I'm not arguing with it. Here's what I've been into Lately.

ICYMI — Lately #004: The IC Question, Finding Focus, and All Things iOS 27 »

Reading: A Decision Makers deep dive

Quick disclosure: I'm biased here. Decision Makers — Forter's customer storytelling series — is something I helped build during my time there, so take this one with a grain of salt.

Myles Madden broke the whole campaign down in his newsletter, Campaign Telemetry, and it's a good read if you want someone else's take on the strategy behind it.

What we were actually chasing was simpler than strategy: telling people's stories around who they actually were, with the job title coming second. Deniz Ertan's page opens with her garden and the story of winning a green card lottery — eBay doesn't come up until four chapters in. Instacart's Shivendra Kishor's starts in the kitchen and the court with cooking and badminton.

The bet was that the same thing that made someone good at their job was usually rooted in their passions outside of it, and if you led with that, the professional stuff would earn its place on its own.

Getting to do that kind of storytelling — sitting with someone and asking about their life instead of just another use case — is some of the most rewarding work I've done in my career. Watching someone outside the building notice that on their own was a nice bonus.

Watching: Life on Mars, with cardio

The treadmill rule is still very much alive, which is the only reason I'm finally catching up on Season 5 of For All Mankind.

I got hooked on this show years ago for the same reason I get hooked on most sci-fi: the "what if." What if the Soviets beat the U.S. to the moon? What if that one change in 1969 kept cascading for decades? This season picks up well into that cascade — Happy Valley is a real colony, and Earth wants more control over that colony on Mars than they're is willing to give up. A fascinating political power struggle (and one we'll never actually see play out in our lifetimes).

Using: Finally, the Siri we've been waiting for

Last edition, I joked that I shouldn't install the iOS 27 developer beta on my daily driver, but probably would anyway. Update: I did.

I've run nearly every developer and public beta Apple's shipped for the last seven or eight years — sometimes for the features, but mostly because I have zero self-control around "the latest and greatest." iOS 27 is, by a wide margin, the cleanest one I've installed to date. Battery drain's been minimal, and it's noticeably snappier than the official iOS 26 build I was running before.

And it's the best version of Siri there's ever been (and the one we were promised years ago).

The new Siri launched at WWDC earlier this month, and the headline feature is personal context — it can actually look across your messages, email, and calendar instead of starting from zero every time you ask it something.

A real example: my nephew's birthday party invite had gotten buried in the family group chat, so I asked Siri to pull the date, add it to our family calendar, and check for conflicts. A few seconds later, it confirmed we were free and the event was on the calendar. Old Siri would've needed three separate questions — and even then, it would've been faster to just handle it myself.

Wild Card: Resetting my productivity stack

For the first time in a while, I'm not locked into whatever software stack a job handed me. Goodbye, forced Google Workspace and single sign-on dictating my life. So I've been using some of this in-between time to rebuild my daily tools on purpose instead of inheriting them.

A few things are already settled (Todoist for tasks management isn't going anywhere). But for browser, email, notes, and the AI assistant I lean on, I've landed on Safari, Apple Mail, Apple Notes, and Claude. Mostly because, aside from Claude, they're native, they play nicely with the new Siri, and I haven't found a good enough reason to leave any of them.

Calendar, however, is where I'm stuck. I have a long-standing grudge against Google Calendar, but it somehow still functions better day-to-day than Apple Calendar does. I've poked around apps like Fantastical in the past and liked pieces of it, but I'm trying not to turn my calendar into another monthly subscription.

It's a small, strange, but fun freedom, getting to pick all this on purpose instead of inheriting it by default.

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That's Lately #005. If you've got a take on the new Siri, a calendar app you swear by, or want to tell me I'm wrong about Apple Calendar, hit me up at hello@joetacosik.com or on LinkedIn.

Talk soon!