In this episode, Damashe uncovers a hidden switch that finally makes his mute button work the way he wants—after months of assuming he needed to rewire it. Meanwhile, Michael shares a chaotic behind-the-scenes story from an in-person board meeting, complete with misbehaving audio gear, last-minute fixes, and some DIY mix-minus routing.

The two dive into:

• Why assumptions and leading questions can steer you wrong—even with AI.
• Lessons learned from a tough live audio setup and the temptation to beat yourself up over tech failures.
• Creative ideas for talkback communication systems using Shokz, Zello, and even FaceTime Audio.
• Android experiments: Michael’s iMessage-on-Pixel attempts, thoughts on BlueBubbles, and the appeal of the Pixel 9.
• VM cleanup strategies and the case for consolidating multiple virtual machines into one solid Windows environment.
• Decisions around Google Workspace vs. DIY setups for small teams—and why simplicity may win.

Plus, a quick reminder: new episodes drop Monday evenings. Follow the TW bot on Mastodon to stay updated.

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In this episode, Michael admits he never called Apple—no surprise there—and shares what happened instead: experiments, frustrations, and the joys of not resetting VoiceOver live. Damashe breaks down his complicated relationship with to-do list apps, from OmniFocus quirks to why he’s sticking with Todoist (despite some platform inconsistencies).

We also dive into ChatGPT’s deep research mode and how Michael used GPT and Google Apps Script to streamline weekly workflows—what used to take hours now takes seconds. There’s talk of accessibility in Google Sheets and Docs, frustrations with VoiceStream Reader, and Bluetooth weirdness with Apple’s audio routing.

And yes, that one setting in Parallels that makes Mac/Windows integration so much better? We finally figured it out. You’ll want to hear this if you use SharpKeys and Keyboard Maestro.

Bonus rants: the B device still sucks, the Plod is promising, and surprise—your notifications don’t mean what you think they mean.

Links Mentioned:

• Review: “I Outsourced My Memory to AI and All I Got Was Fan Fiction” – The Verge
• Technically Working Tip Jar

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Michael shares some recent work slip-ups tied to automation and explains how a small formatting mistake threw off email quick links for thousands of people. He walks through how he’s checking Zoom links more carefully now using JAWS sounds and VoiceOver tweaks—and vents a bit about Apple's pronunciation settings and table editing headaches on the Mac.

Damashe jumps in with thoughts on where VoiceOver stands in Apple’s priority list (spoiler: not high), and they both trade tips for avoiding Safari freeze-ups and digging into macOS settings. There's also some behind-the-scenes talk about how automation projects are making them think more like coders, even if they’re just feeding prompts to GPT.

They talk about:

• Renting vs. buying speakers for events (and how hotel AV pricing is wild)
• Michael’s growing collection of smart appliances (yes, Sniffy McGee the vacuum makes a return)
• Network upgrade ideas, attic fails, and future cable runs
• Damashe’s vending machine script to automate reporting from Cantaloupe
• Using Hazel with GPT to build automation rules on the Mac

Toward the end, Michael shares a serious PSA about a family member who nearly fell for a phone scam—and why it's time to have a plan in place before you get a scary-sounding call. Damashe adds tips for protecting yourself as deepfakes and voice cloning get better and easier to pull off.

They wrap it up with a quick look at download numbers, what’s working with the “live to tape” style, and why Damashe regrets not buying that fancy Dyson fan when it was on sale.

Links & Mentions:

• Email us at feedback@technicallyworking.show
• Follow the show: @tw@technically.social
• Michael: @payown@dragonscave.space
• Damashe: @damashe@technically.social
• Use #TechnicallyWorking on Mastodon to chat with us
• And yeah—huge thanks to our tip jar supporters. You're the real MVPs.# Episode Notes

Notes go here

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This podcast is powered by Pinecast. Try Pinecast for free, forever, no credit card required. If you decide to upgrade, use coupon code r-431b7d for 40% off for 4 months, and support Technically Working.