AI to troubleshoot tech problems? Here's how it helped me solve a stubborn issue, and how you can use it to fix your own.

In this episode, Carl talks with Stephen from Digital Serenity about the growing frustration of living in a digital world where apps, passwords, and account systems create constant friction, including real examples of being locked out of essential services like parking apps. They discuss why even tech-savvy people can get trapped by company-side login loops, and why using an agnostic password manager (rather than browser-based password saving) helps across browsers and devices. Stephen advises avoiding single sign-on when possible due to privacy and identity risks, explains two-factor authentication, and describes how passkeys work and why they still often require fallback passwords.  He outlines his coaching-style service, including audits, “lost phone” simulations, and five pillars of digital health, and emphasizes using tech to improve life while maintaining an analog balance. 00:00 Welcome Back Stephen 00:15 Digital Friction Reality 02:08 Parking App Password Fail 05:22 Digital Locksmith Analogy 07:29 Browser Password Managers 10:53 Privacy And Neural Data 14:49 Passkeys And Simulations 16:46 Five Pillars Coaching 19:31 Password First Principles 23:38 AI Search And Photos 25:15 Audience Q And Wrap 28:46 Portuguese Farewell Outro 29:19 A Team Promo Tag

We’ve all been there. Standing in line, staring at a screen, or refreshing an app — only to discover that the service we desperately need has chosen this

I detest websites and podcasts that don’t ‘splain stuff to me

Raycast 2.0 is a great update, but one change to the clipboard history has completely broken my workflow. Here's what changed and how to fix it.

Xfinity Customer Service Fail: How a Minor Playback Glitch Became a Customer Service Defining Moment I’m a long-time Xfinity customer. A recent customer service experience has transformed me from an ambivalent advocate for a service that essentially operates as a monopoly in my area into a reluctant customer (at best), who has been the target of fraudulent transactions, deceitful practices, and accusatory, unempowered, and untrusting customer service. This is the story of how annoying audio and video glitches on my television escalated into a customer service fiasco. Just trying to get my TV to work…

Dear diary, I need to vent. I’ve started realizing that we live in unexpectedly interesting times – so much so that what feels relevant right now can become just a pleasant memory amid the constant flood of technology. I’m frustrated with Xiaomi. How desperate do you have to be to name your phones in a way that […] Post Diary of a Grumpy Old Geek: Laughter, Frustration, and the Xiaomi 17 Pro Max at Root-Nation.com.