Roundabout 1.1 is out. The headline change: it can now generate a one-line summary for whatever app you’re actively using — not just Terminal and Safari, but Notes, Mail, Xcode, anything with visible on-screen text. Same idea as before, just no longer limited to the two apps it started with.

A few sensitive categories (password managers, Messages, Mail) are left out by default, and you can opt any app in or out yourself from the new Settings window in the menu bar.

Download Roundabout for Mac →

Free, signed and notarized. Requires macOS 26+. See the 1.0 post for the full install steps, or the source on GitHub.

In football, every once in a while we catch a glimpse of the ref’s camera, or a view from the sidelines, or behind the goal. These kinds of angles start to explain the geometry of the field as the players see it and that’s where I want to be. Looking at the game from a vantage point that helps me understand the players choices and athleticism. Imagine if we could be down on the field, seeing the lanes and the plays from their perspective.

The game has so much drama, I want the camera to reflect that. The question is, how do you get cameras into these positions and not disrupt the game. The further the camera is away from the action, the more we have to zoom, which compresses space and distorts the relationships I want to grasp better.

Cameras attached to players with stabilization? Drones? There’s no easy answer. Maybe there’s a purpose built team or robots that are very good at staying out of the way and covering the action or maybe there’s a realtime solution that allows us to scan the action and place the camera anywhere in the reconstituted scene. It doesn’t exist yet, but I think it will be possible soon…

The goal is to be inside of the action and see the players think about their choices and understand the plays from their vantage point.

Roundabout 1.0 is out — the first release I’d call stable rather than “something I’m working on.”

If you haven’t seen it before: Roundabout is a free macOS menu-bar app that remembers your actual working contexts — not just which app you were using, but which Terminal tab, which Safari tab, which specific window — and jumps straight back into one with a single Option-Tab gesture, the same way Cmd-Tab jumps back to your last app. It generates a short summary of what’s actually happening in each tab (entirely on-device via Apple Intelligence by default, so nothing about what you’re working on leaves your Mac), so when you switch, you can actually tell what you’re switching into.

Download Roundabout for Mac →

Free, and signed and notarized by Apple, so there’s no Gatekeeper warning to click through. Requires macOS 26+.

Install

1. Download the DMG above and open it.
2. Drag Roundabout into Applications.
3. Launch it from Applications (or Spotlight) — it lives in the menu bar, not the Dock.
4. Grant Accessibility (for the Option-Tab switcher) and Automation (for Terminal/Safari tracking) when prompted. Both take effect immediately — no need to quit and relaunch.

What’s new in 1.0

• A proper signed, notarized build — no more workarounds to get macOS to trust it.
• The install flow itself got smoother: granting Accessibility or Automation permission now takes effect immediately, without quitting and relaunching the app.
• Safari contexts now show the page’s domain, so you can recognize a tab at a glance before its summary even loads.

More on how it’s built, and the full story of what went into this release, is on the original post and the source on GitHub.

I’ve long been a user of command-tab on Mac, the App Switcher… haven’t we all. But of late I’ve found, particularly working with AI tools in the terminal and on the web, the context of my work isn’t the application, it’s the tab. Whether it’s Krea or Claude, it’s hard to tell from just the tab what work is happening there. So I wrote an app called Roundabout for context switching - it provides a useful summary of what’s happening in each tab of Terminal and Safari(for now), so that when I switch, I can see what I might want to switch into. I’m guessing there are other apps to support… photoshop or xcode or… but I’m starting with the basics and will grow from here.

Also, this site was created with Claude. It’s based on markdown and keeps an eye on my Obsidian vault for any document with publish:true. It polls every 15 minutes and writes it out to Github, which is picked up by Cloudflare and brought to you. I’ve been thinking about a frictionless blog for a while. I think this might be it.

“I believe the best managers acknowledge and make room for what they do not know—not just because humility is a virtue but because until one adopts that mindset, the most striking breakthroughs cannot occur. I believe that managers must loosen the controls, not tighten them. They must accept risk; they must trust the people they work with and strive to clear the path for them; and always, they must pay attention to and engage with anything that creates fear. Moreover, successful leaders embrace the reality that their models may be wrong or incomplete. Only when we admit what we don’t know can we ever hope to learn it.”

― Ed Catmull, Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration