Welcome to the Friday Wrap-Up for August 7, 2026. This is a short newsletter where I talk about 3 things: What’s on my mind this week, Recommended Reading, and Something Fun. Here's what's on my mind...

On My Mind

Resetting Claude Every 3 Months? My friend Doc Rock sent me an interview with Boris Cherny, who's the head of Claude Code, last week while I was on vacation, and the advice struck me. Cherny basically says we should reset our prompts/projects/skills every time there's a new model. While my estimation after a couple of listens is he's largely talking about Claude Code, my understanding is that Cowork runs on Claude Code.

I don't like this at all; one of the reasons I try to stick with one model is that I don't want to have to retrain some LLM every few months. But this is also why I always say we don't "hire" LLMs. Imagine if you hired someone and then they got that Men in Black flashy thingy every 3 months and their memory was wiped.

I'm not going to reset the memory. I'm going to keep my simple set of directives, and if the LLM gets worse at doing a task, I'll just do that task myself. This is something you generally don't need to worry about with Zapier, Make, or Shortcuts. The technical debt seems to accumulate much, much faster with LLMs. Is the time it saves you worth having to reset or retrain it every quarter?

Recommended Reading

​Destiny of the Republic by Candice Millard: I know shockingly (maybe not shockingly) little about James Garfield. For example, he was a congressman who left his post to fight in the Civil War and did very well. He was nominated for president despite vehemently protesting it. And he was one of the 4 presidents assassinated in office.

Destiny of the Republic is Garfield's story, but it's also one of mental health, and access people had to presidents until the early 20th century, technology, and the evolution of medicine. Alexander Graham Bell is heavily featured as well — I learned a ton about him!

This is the second book I've read by Candice Millard and love her style. She's a fantastic storyteller, and the way she weaves a story together to keep it interesting without it being histrionic is excellent. I highly recommend it.

Something Fun

Walking without headphones: This is my first week back from vacation, and one of my favorite things to do is take a walk before the rest of the house wakes up (I'm often the first one up, but my kids are starting to rival that).

This year, my youngest daughter excitedly accompanied me on each walk. She's a very good walking buddy. But this also forced me to do something I've been trying to do more of: walk without headphones.

I've made it a part of my Year of Digital Detox: be more present with my thoughts instead of having to fill every silence. And while the walks with my daughter were not filled with silence — something I happily subbed for Daddy-Daughter time — my walks at home have been.

I've continued the habit by walking 1-1.25 miles every morning, with nothing but my watch. It's been nice, and if you have a chance this weekend, I strongly recommend you try it.

I'm speaking at Ops Ahoy!

Ops Ahoy is setting sail this September, and I'm so honored to be a Captain this year! In my session you'll learn how to create a framework that sets boundaries and resets expectations in your inbox.

Join us for two days of deep discussion, connection and FUN as we pave the future of operations work. Grab your ticket here: processdriven.co/ahoy ⚓️

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Until next week

Joe