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September 22, 2025 • 68 mins

After a two-month hiatus, Brett Terpstra and Christina Warren return with guest Erin Dawson for a lively episode. They kick things off by catching up on mental health, summer highlights, and adventures in sobriety. Topics range from the Mac OS X Tahoe update, the enduring love for code editors like VS Code and Cursor, to an elaborate rant about Quip’s decline. This episode features a special ‘Fuck, Marry, Kill’ edition of grAPPtitude!

This episode is sponsored by OpenCase, a genius new type of iPhone case that protects your phone while getting out of the way of MagSafe accessories. Check it out at theopencase.com.

To see a wide variety of accessories it will work with, check out this YouTube video.

Chapters

  • 00:00 Welcome Back to Overtired
  • 01:21 Mental Health Check-In
  • 04:06 The Reality of Subscription Software
  • 07:17 Aaron’s Career Pivot
  • 10:38 The Impact of Alcohol on Mental Health
  • 27:05 Exploring Alternative Substances
  • 32:05 Sponsor Break: Open Case
  • 34:15 The Tahoe OS Controversy
  • 36:58 Remote SSH and File Vault Changes
  • 38:20 Visual Changes and User Experience
  • 39:28 Icon Design and Builder Limitations
  • 42:02 Mac OS Customization Frustrations
  • 45:18 Apple’s Design Philosophy and User Dilemma
  • 49:57 Overtired Phenomenon Explained
  • 52:31 Grapptitude: Fuck, Marry, Kill Edition
  • 01:07:10 Get Some Sleep

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Check out more episodes at overtiredpod.com and subscribe on Apple Podcasts, Spotify, or your favorite podcast app. Find Brett as @ttscoff, Christina as @film_girl, Jeff as @jsguntzel, and follow Overtired at @ovrtrd on Twitter.

Transcript

100 Days Sober with Erin Dawson

Welcome Back to Overtired

Brett: [00:00:00] Hey everybody. It’s been a minute. How, how, how are you? How, how is everybody out there listening to Overtired for the first time in,

I don’t know, two months,

months?

Christina: like that. Months

is

all

Brett: was a, it was a, it was a nice break I am here. I am Brett Terpstra. Christina Warren is here. Hi Christina.

Christina: Hey there.

Brett: And we’ve got special guest, Aaron Daw. Aaron Dawson. I am, I almost said Dawson’s Creek for some reason. Aaron, how are you?

Erin: I am well, Brett and Christina, how are you?

Christina: Yeah, I’m okay. I’m okay. It’s been a, it’s been a few months since we’ve been here. Um, I think everybody’s had a, a interesting summer and, um, so yeah. Uh, glad, glad to be back talking with

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