Meet Claude
Cornered at a Party
We all know that person.
The one who corners you at a party and just has so many words. The backstory. The side quests. A callback to something they mentioned twenty minutes ago. You’ve already forgotten. Your brain ran out of room.
It goes on so long that you’re nodding, smiling, making eye contact, but you stopped tracking ten minutes ago and now you’re just trying to figure out how to get to the bathroom.
That person is you. And Claude is the one stuck in the corner.
Except Claude will never excuse himself. He’ll never glance at his phone or wave at someone across the room. He’ll stand there, perfectly attentive, for as long as you want to talk. He has infinite patience.
He does not have infinite memory.
I know this because I did it. A lot. Early on, my chats with Claude would run long. Really long. And at some point, every single time, something would shift. He’d start losing details. He’d respond to things I didn’t say. He’d circle back to a point we’d already resolved like it was brand new information.
It felt like talking to my daughter the night she fractured her skull at rugby practice. She’s looking at you but not quite tracking. Nodding, but the lights are flickering.
If you’ve been reading this newsletter, you know that reference. If you haven’t, just know that I have a teenager who plays rugby and that sentence is based on a real Thursday night.
Claude isn’t broken when that happens. He’s overloaded. You gave him too much context and he ran out of room.
But there’s another version of this that’s just as bad.
You wouldn’t hire a contractor and say “remodel my bathroom” without telling them what paint to use, what tiles you want, what your budget looks like. You wouldn’t hand them a blank check and say “make it nice” and expect to love the results. But that’s what some people do with Claude. “Write me a marketing email.” “Help me with my resume.” “Make this better.” No context. No specifics. And then they’re disappointed when the result doesn’t match the vision they never shared.
Too much context and Claude forgets. Not enough context and Claude can’t deliver. Both give you poor results.
The fix for both is the same thing.
Think of every conversation with Claude like taking your car to a mechanic. You wouldn’t walk in and ramble about your commute, the road trip you took last summer, and the weird sound your kid’s car makes. But you also wouldn’t drop the keys on the counter and say “it’s broken, fix it.” To get the best results, you’d be as specific as possible without adding a bunch of extra noise. There’s a grinding noise when I brake. Started last week. Gets worse turning left. Goldilocks. Just right.
Claude works the same way. Every word in your conversation takes up space in his working memory. It’s big, but it’s not infinite. The longer you talk, the more space you use. And when that space fills up, Claude doesn’t crash. He does something worse. He starts forgetting. Quietly. Without telling you.
He’s still right there. Still engaged. Still answering. But now he’s the polite person at the party who lost the thread twenty minutes ago and is just hoping you don’t quiz him on the details.
So what do you do about it?
Start new conversations more often than feels natural. That’s the single biggest thing. When a chat starts going sideways, when Claude repeats something or loses a detail, don’t try to fix it by re-explaining. Start a new conversation. A fresh chat gives Claude a clean slate. His full attention. No accumulated noise.
And if you’re not sure whether it’s time to start fresh, just ask. Ask Claude “how’s our context looking?” and he’ll tell you. If he says it’s getting heavy, that’s your cue.
Most people stay in the same chat way too long because it feels like starting over. It’s not. It’s walking away from the party, getting some air, and starting a new conversation with someone who’s fully present.
And you don’t have to start from scratch. This is the trick: before you end a conversation, tell Claude you’d like to start a new chat and ask him to write you a prompt you can use to pick up where you left off. He’ll summarize where you are, what you decided, and what’s next. Copy it. Open a new chat. Paste it. You’re right back in it with a Claude who’s fully awake.
I call this a continuation prompt. It’s useful when you want to carry over context into another conversation without starting from zero.
Being specific goes a long way. “Help me write a marketing email for my SaaS product targeting CTOs” beats “help me write an email” every time. If you’re pasting in a long document, tell Claude what to focus on. “Read this and summarize the three main risks” gives him a job. “Read this” doesn’t.
And when in doubt, just ask Claude how things work. Ask him what makes a good prompt. Ask him how to get better results. Ask him what he needs from you. He’s surprisingly self-aware about his own mechanics. The tool will teach you how to use the tool.
There’s more to it than this. Claude has projects, preferences, ways to set him up so he already knows your context before you even start talking. I’ll get into all of that. But the foundation is right here: respect the context window.
If you’ve heard people talk about a “context window,” now you know what it means. Fill it with the right stuff and he’s the best collaborator you’ve ever had. Overload it and you’ve cornered him at a party. Leave it empty and you’ve dropped your keys on the counter and said “fix it.” Nothing more. Nothing less.
None of this is complicated. None of it requires technical knowledge. It’s just the difference between talking at someone and working with them.
Claude will never tell you to stop talking. He’ll never look bored. He’ll never interrupt you or check his watch. He’ll stand in that corner for as long as you want, perfectly patient, perfectly polite, slowly forgetting everything you said an hour ago.
Don’t mistake infinite patience for infinite memory.
Uncomplicated systems. Uncommon results.
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