It’s been a busy few weeks over here and you haven’t heard from us. So it feels like a good time to get back to it with a story about something we tried, put down, and came back to later.

A year ago, our friend Catherine replied to one of these newsletters with an idea:

“I'm SHOCKED this doesn't exist: a screenshot capturing tool that translates your calendar to plain text as a less aggressive, more convenient way to share your availability.”

Honestly, great idea. And it sounded simple enough to test, so we built it.

Take a screenshot of your calendar, drop it in, and get your availability back as plain text.

And… it never quite worked.

We’d give it a screenshot and get half the times. Tweak the instructions, get the other half. One day would work, another would break it. We tried different models, prompts, crops. It would get just close enough to keep us going, but it was never perfect.

So we put it down.

Then, recently I was replying to an email trying to find a time to meet. Do I send my calendar link? That feels like too much. Do I type out all my availability? I can, but.. I gotta do all the timezone math.

And this idea popped back into my head.

The screenshot version had been appealing because there was basically no setup. But.. what if we embed it right in your calendar?

So we made it a Chrome extension and let it read the calendar already sitting in the browser.

It worked the first time.

Avail in action

How it Works

You are already looking at your week in Google Calendar. This reads the calendar you have open, figures out the gaps, and turns them into something you can paste into an email or Slack:

Wed, Sep 2, 12–1PM CDT (1–2PM EDT)
Thu, Sep 3, 10–11AM CDT (11AM–12PM EDT)

And it has some nice little features: you can ‘sandwich’ against other meetings to leave focus time for yourself. And you can easily offer multiple timezones.

No impersonal booking page. You don’t have to make your calendar public. Just the thing you were about to type yourself, but automated.

Notes from Building

The first time around, it seemed like maybe AI could look at something the way we do and make sense of it, so we treated the calendar like an image. That felt natural because that’s how we experience a calendar: we look at the week, see the gaps, and understand what’s free.

But the screenshot was making the job harder. It stripped away the structure and left it trying to rebuild the calendar from pixels. This time, instead of asking the computer to imitate the human part, we gave it the version it already understood.

A year later, AI is doing some genuinely wild things. We’re reading about models finding bizarre ways around instructions, hiding mistakes, or effectively jailbreaking themselves.

At the same time, I think we’re getting better at the less flashy part: understanding what these tools are actually good at, what they’re still surprisingly bad at, and how to give them the kind of work they can do well.

The technology is getting better. But so are we at understanding how to use it.

Built with ❤️ by Township

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