Resetting Claude Every 3 Months? [Friday Wrap-Up]

This week I talk about a piece of advice from Boris Cherny, head of Claude Code — that you should reset your prompts, projects, and skills every time a new model ships — and why I’m not doing it. Then a recommendation for Destiny of the Republic, Candice Millard’s book on James Garfield, and why I’ve started walking a mile every morning without headphones. Plus a quick promo: I’m speaking at Ops Ahoy this September on setting inbox boundaries.

Links:

These episodes are about taking more time off — especially on the weekends. The best way you can do that is by having a good system. If you’re not sure where to start, head over to https://streamlined.fm/quiz. Answer a few questions, and I’ll send you exactly where you should start to build a less overwhelming business.

View the episode transcript

  • (00:00) – Intro
  • (00:32) – OMM: Resetting LLMs
  • (03:19) – Recommended Reading: Destiny of the Republic
  • (05:19) – Taking a Walk Without Headphones
  • (07:06) – Event Promotion & Outro

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Streamlined Solopreneur helps overwhelmed solo business owners go from overwhelmed to having their time back.

Each week, Joe Casabona shares one practical idea — a system, tool, or strategy to help you get your time back without selling your soul to AI…and run your business without sacrificing the rest of your life, or your health.

Looking for a place to start? Take the Solo Systems Starter Quiz. 60 seconds, 8 questions, and I will tell you what system you should build first, and exactly how to build it. https://streamlined.fm/quiz 

Connect with Joe on LinkedIn: https://www.linkedin.com/in/jcasabona/

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Hey everybody and welcome to the Friday wrap up on Streamline Solopreneur, a short

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episode where I cover three things, what’s on my mind this week. Recommended reading

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and something fun. This is the show that helps overwhelmed coaches, consultants,

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and service providers build systems so their business doesn’t depend on them. Hopefully

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this week’s curation gets you thinking about your own systems. Before you close the

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laptop for the weekend, I’m your host, Joe Casabona, and here’s what’s on my mind

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For August 7th, 2026,

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first on my mind resetting Claude, every three months my friend Doc Rock sent me

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an interview with Boris Cherney, who’s the head of Claude Code last week while I

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was on vacation. And the advice struck me.

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Cherney basically says we should reset our prompts, projects, skills every time there’s

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a new model.

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while my estimation after a couple of listens is he’s largely talking about Claude

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Code. My understanding is that co-work runs on Claude Code.

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I

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don’t like this at all.

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One of the reasons I try to stick with one model nay, one

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large language model in general, right? I have gone all in on Claude, is that I don’t

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wanna have to retrain some LLM every few months.

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But this is also why I always say we don’t hire large language models. Imagine if

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you hired someone and then they got that men in black flashy thingy thing every three

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months and their memory was wiped.

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Kay, have you ever flashy thing me? No, I ain’t playing with you, Kay. Have you ever

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flashy thing me? No.

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I am not going to reset the memory. I’m going to keep my simple set of directives

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and if the large language model gets worse at doing that task, I’ll just do the task

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myself.

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This is something that you generally don’t need to worry about with Zapier or make

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or shortcuts.

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The technical debt seems to accumulate much, much faster with large language models

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because they’re evolving so quickly. So my question for you is, is the time

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it saves you worth having to reset or retrain your large language model every quarter?

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The discovery of it doing the job worse when you expect it to be consistent?

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Is it worth it in these cases? Or maybe a bigger question is, are you even checking

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the work of the large language model? ’cause this is something that you need to do

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and this is another reason why say we don’t hire large language models. ’cause yes,

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we should check in with our employees or contractors, but

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we should also trust that our employees or contractors are not going to dramatically

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change

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multiple times per year.

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So I’d love to know what you think of this. Do you have something on your mind? How

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are you going to approach

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resetting large language models? Let me know over@streamlinedfeedback.com. You can

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write in or leave a voice note. I might even play it on the show.

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Okay, so for recommended Reading Destiny of the Republic by Candace Millard,

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this is a book that I finished while I was on vacation and thoroughly enjoyed it.

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I know shockingly, or maybe not shockingly little about James Garfield. I said this

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to my father-in-law and he goes, most people don’t know anything about James Garfield.

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and he’s like a history buff. So,

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I, I know shockingly little about James Garfield, for example, he was a congressman

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who left his post to fight in the Civil War and did very well at that. He was nominated

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for president despite vehemently protesting it. He did not want this job,

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and he was one of four presidents assassinated in office.

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Destiny of the Republic is Garfield story, but it’s also one of mental health and

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access. People had to presidents until the early 20th century.

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People could just walk in to the president. They had like open calling hours or open

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office hours multiple times per week.

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And while that has changed for the better because of some of the events of this book,

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it’s a sort of access that members of the press barely get today.

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It’s also a story of technology and evolution of medicine.

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Alexander Graham Bell is heavily featured in this book as well, and I learned a ton

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about him.

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This is the second book I’ve read from Candace Millard. I’ve got it right here on

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my desk. Destiny of the Republic by Candace Millard.

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And I love her style.

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She’s a fantastic storyteller and the way she weaves a story together to keep it

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interesting without it being histrionic is excellent. I highly recommend it. It’s

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also,

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uh, the book is the inspiration for the Netflix series, death by Lightning, which

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has one of my favorite actors Nick Offerman in it. So I highly recommend this book.

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I’m even more excited to watch this series now.

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Okay, moving on to something fun or maybe just something interesting. And so I think

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this week’s recommended reading was, is a fun one,

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walking Without Headphones. This is my first week back from vacation and one of my

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favorite things to do

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on vacation is take a walk before the rest of the house wakes up. I’m often the first

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one up anyway, but my kids, especially my oldest, are starting to rival that

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this year. My youngest daughter excitedly accompanied me on each walk. She is a very

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good walking buddy,

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but this forced me to do something I’ve been trying to do more of anyway, which is

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take a walk without my headphones, without listening to music or a podcast. During

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these walks, I made this part of my year of digital detox be more present with my

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thoughts instead of having to fill every silence. And while the walks with my daughter

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were not filled with silence, something I happily subbed for daddy-daughter time.

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My walks at home have been, I’ve continued the habit by walking one to one and a

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quarter miles every morning

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with nothing but my watch. I it, it’s been nice, it’s been nice listening to the

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sounds of the town where I live and not have something filling my brain, letting

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my mind

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wander, letting myself be present

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with myself.

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It’s been nice. And if you have a chance this weekend, I strongly recommend you try

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taking a walk without your headphones or just sitting in silence.

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It’s something that we don’t do enough of these days.

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Okay, so there is no automation of the week this week, but I do have a quick promo

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if you want to learn more,

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hands-on

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about my processes. I am speaking at an event called

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SHO in Philly in September.

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Sho is setting sale this September and I am

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honored to be a captain this year. In my session, you’ll learn how to create a framework

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that sets boundaries and resets expectations in your inbox.

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Join us for two days of deep discussion, connection, and fun.

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As we pave the future of operations work.

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Grab your ticket@processdriven.co slash ahoy.

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That’s process driven.co/a

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OY. I will have a link to that and everything we discussed in the description for

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this episode.

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But that’s it for this episode of the Friday wrap up. These episodes are about taking

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more time off, especially on the weekends, and the best way you can do that is by

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having a good system. If you are not sure where to start, head over to streamlined

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fm slash quiz, answer a few questions and I’ll send you exactly where you should

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start to build a less overwhelming business.

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Thanks so much for listening and until next time, I hope you find some space in your

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weekend.

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