Press Pause — Season 2, Episode 4

I had my first-ever guest on Press Pause, and it was long overdue!

Tom Anderson — Apple enthusiast, IT professional, and co-host of the Basic AF Show joined me for a conversation about notes apps, AI tools, devices, and the eternal question of whether the madness of chasing new apps ever ends.

We covered a lot of ground, so let’s get into it. You can find the episode on:

YouTube | Spotify | Apple Podcasts

The question I always come back to is: why do we keep switching?

Tom has been on Craft Docs since 2020, with one detour through Bear along the way. He left temporarily when Craft seemed to be chasing the enterprise market and that shift gave him pause. But Craft eventually came back to its roots as a personal knowledge management tool, and Tom came back with it.

Craft is now 90% of where he works, both for personal projects and work.

What makes Craft stick for Tom is the document-as-container model.

You don’t just have flat notes, you have documents that can hold nested subpages, which is a game-changer for project work. One thing that trips up new users is the difference between a card and a page inside a document. They’re functionally the same thing (both are just subpages), but the card gives you a visual, styled block while a page shows a small icon and preview text.

It sounds simple, but it’s one of the first things people ask about in the Craft community.

For me, Apple Notes is still home base.

But I’ll be honest, search in Apple Notes has been frustrating. You can type the exact title of a note and it’ll surface two or three results that have nothing to do with it.

That’s a gripe I need to make a video about, because for a tool that’s supposed to be simple and fast, that’s a meaningful miss.

A few takeaways from our notes app conversation:

Tom also mentioned that Craft’s task system has been replacing Things 3 for him.

The pitch is compelling: when you click into a task, it becomes a full Craft note. You can sketch, add images, build tables — all within the task itself. So instead of taking notes in Craft about a task you’re tracking in Things, you just stay in Craft.

It’s still a work in progress, and Tom gave it the year to prove itself, but early results are promising.

AI came up a lot and not just the polished, consumer-facing stuff.

There’s been a wave of open-source AI agents that let you install a chat interface on your local machine and connect it directly to your files, your email, and basically anything a human can do on a computer. One of them, originally called Clawdbot and now going by OpenClaw (after Anthropic had some concerns about the name), has been making the rounds.

People were buying Mac Minis hand over fist to run it a few weeks back.

Neither of us have installed it on a personal machine and we’d advise against it for most people.

Tom flagged a 1Password article noting that a lot of the “agent skills” these tools use have turned out to be malware. When you hand something unfiltered access to your computer, you don’t always know exactly what it’s doing. That’s a hard pass for both of us on a personal device.

That said, we’re both genuinely excited about where agentic AI is heading when it’s done responsibly:

Context is still the biggest variable with AI right now.

Without it, you get generic results. Feed it the right documents, i.e., your channel data, your project notes, your writing style and it becomes genuinely useful.

I’ve been refining my Claude projects to work around context window limits by breaking up large project files into smaller, focused chunks.

It helps.

Here’s where things get interesting for a couple of self-described tech enthusiasts who have been quietly not upgrading everything every year.

Tom’s setup:

⠀My setup:

The common thread: we’re both sitting on Apple Silicon machines that are aging by Silicon Valley standards, and neither of us feels a strong pull to upgrade.

The M2 Max still handles a couple of 4K editing timelines without breaking a sweat. Tom’s 2020 Mac Mini is doing fine for what he needs. The M5 chips are genuinely impressive, especially for heavy video workflows, but if you’re not doing multiple streams of 8K footage, the generational leap doesn’t feel urgent.

Tom also made a good point about the new Magic Keyboard for iPad. If you’re still on the original version from a few years back, the new one is a meaningful upgrade: quieter trackpad, aluminum palm rest, function row, better keys overall.

Tom shared a screenshot of his iPhone home screen. No widgets. And badges on basically everything — including 826 unread mail messages.

I have a near-physical reaction to that. Somewhere around pandemic time, I went deep on notification cleanup. My system now: morning and evening notification summaries, and if something sits in the summary for six months without me tapping it once, the notification gets turned off. Clean home screen, no badges, no anxiety spiral.

Tom’s take? They’re just red circles. The CVS down the street has a flashing LED sign and he doesn’t stress about that either. And honestly — he’s right that we’re all wired differently. His co-host Jeff has the same reaction I do. Tom genuinely doesn’t care. Both approaches are fine. Focus modes and notification summaries have made it easier than ever to build the system that works for you, whether that’s obsessively clean or cheerfully chaotic.

One thing both of us agreed on: a daily summary notification from your task manager — just a morning nudge of what’s on deck — is a great habit. It gets you to open the app, triage the list, and actually decide what you’re going to do today rather than pretend your inbox is a to-do list.

The PlayStation vs. Xbox debate never really ends. Neither does the notes app debate, the iPad-as-computer debate, or the Android vs. iPhone debate. They just get new clothes every few years. Ford vs. Chevy had the same energy decades ago.

These are all just tools. What matters is whether the tool helps you get something important done. The moment you stop treating your app choices as identity statements is the moment the whole thing gets a lot less exhausting — and a lot more useful.

That’s the thing I keep coming back to.

Thanks to Tom for being the first guest on Press Pause!

If you want more of his perspective on all things Apple and productivity, check out his newsletter at tomfanderson.com, find him on Threads at TomAnderson, and listen to the Basic AF Show at basicafshow.com. He is also here on Substack at !

If you enjoyed this one, a like, comment, or five-star review on Apple Podcasts goes a long way.

Talk to you in the next one!

— Bill