Staying Organized with AI: Managing Context Windows & Projects
Every AI user hits this wall: your conversation gets too long, the AI starts drifting, and you can't find that brilliant idea from three weeks ago. Bert and Julianna share battle-tested strategies for staying organized as your AI work scales.
Episode Summary
Bert shares his battle with AI context windows - that frustrating moment when Claude says "start a new conversation" just as you're making progress. This sparks a deep dive into how different AI tools handle long conversations, when they drift, and practical strategies for staying organized.
From creating "cheat sheets" for your AI to organizing projects, backing up your work, and knowing when to start fresh - this episode is packed with actionable advice for anyone using AI regularly. Plus: why AI's memory limitations might actually be a point where humans still win.
Episode Timeline
Happy Friday
Bert and Julianna kick off with a Friday recording session. Bert's wearing something other than his signature black polo.
Waging War with Context Windows
Bert introduces the challenge: choosing which AI to use based on context window limitations. Claude cuts you off, ChatGPT slows down, Grok stays focused longer.
Creative vs Coding Conversations
Where Bert hits the limit: deep architecture and coding work. Going back and forth on "why" decisions, not just "what" to do.
Like Calling Tech Support
"It's like I'm calling into tech support... I've spent minutes explaining what's going on and then I have to talk to someone new." The frustration of losing context.
Does This Apply to Book Writing?
Julianna asks: If you're using GPT to organize ideas for a book over three months, does it drift? Bert: "Totally. Drift is a more accurate term."
Claude's Memory Feature
Claude can now check previous conversations. "Let me look" - it searches your chat history to maintain continuity across sessions.
The Project Manager Problem
Bert connects this to a timeless challenge: big projects are overwhelming. Where do you start? How do you organize context?
Notebook LM for Research
Bert's tool for huge documents: Google's Notebook LM. Drop in congressional bills, documentation, ask questions, or convert to podcasts.
Best Practices: Cheat Sheets
Bert's strategy: Create multiple small conversations about specific aspects. Then make a "cheat sheet" - ask the AI to summarize what you've discussed so you can start fresh.
Google vs ChatGPT
Julianna's observation: Gen Z asks ChatGPT, Millennials Google it. Different approaches to finding information, both creating conversation clutter.
Projects in ChatGPT & Claude
Both tools have "Projects" features. Bert's example: Family cartoons for his boys, separate from work. Keeps context siloed with specific instructions per project.
Code Repositories & Context
Bert's coding workflow: Python script pulls README, file tree, architectural decision records into a single file. Drop it in Claude when starting fresh.
Social Media Example
Julianna's scenario: Using AI for social media ideas over three months. Setting up projects, giving feedback, going on tangents. How do you stay organized?
Documentation is Key
Bert's recommendation: Save AI summaries to Notion, OneNote, or Google Docs. Ask the AI to create a cheat sheet for itself, then document it.
Performance Degradation
Long conversations slow down progressively. ChatGPT and Grok get slower with more history. Claude cuts you off to maintain speed.
Score One for Humans
Julianna: This is where humans win. A developer or marketer who's been working on something remembers the context. AI is like a new intern every time.
The Hook Trap
If you train AI on the hooks you like, all your hooks sound the same after a year. Humans bring fresh perspectives and challenge themselves to evolve.
"I Fired Grok"
Bert shares a story of pushing Grok too far. It started forgetting things and led him into a coding corner. Had to go back to manual debugging.
Action Items Summary
Julianna wraps with actionable steps: 1) Clean up miscellaneous chats, 2) Make backups on "digital paper," 3) Attach information to specific projects, 4) Keep living documentation that evolves.
AI Organization Strategies
Create AI Cheat Sheets
The Strategy: Ask your AI to summarize what you've discussed so you can start a fresh conversation with that context.
How to do it: "We've been talking about this for a while. I'd like to start a new conversation because my context window's running out. Please create a cheat sheet that summarizes our discussion so I can pick up where we left off."
Use Projects for Organization
The Strategy: Both ChatGPT and Claude have "Projects" features. Create separate projects for different areas of work.
Benefits: Siloed context, specific instructions per project, ability to add relevant files, keeps personal and professional work separate.
Back Up to "Digital Paper"
The Strategy: Save important AI outputs to Notion, OneNote, Google Docs, or your documentation system.
Why it matters: AI conversations are ephemeral. Documentation creates a permanent record you can reference, search, and build upon.
Refresh Context Regularly
The Strategy: Start new conversations periodically to maintain performance and clarity.
When to refresh: When responses slow down, when you notice drift, when you're ready to move to the next phase of work. Use your cheat sheet to jump back in.
Context Window Comparison
| AI Tool | Behavior | Best For |
|---|---|---|
| Claude | Forces new conversations to maintain speed and quality | Short, focused sessions with high-quality responses |
| ChatGPT | Slows down progressively as conversation length increases | Long conversations when speed isn't critical |
| Grok | Stays focused longer than ChatGPT but eventually drifts | Extended work sessions requiring sustained focus |
| Notebook LM | Designed for huge documents and research tasks | Analyzing large documents, bills, documentation |
Your AI Organization Action Plan
🧹 Clean Up
- • Delete or archive miscellaneous one-off questions
- • Organize conversations into projects
- • Remove conversations that are no longer relevant
- • Think of it like cleaning your email inbox
💾 Make Backups
- • Save AI summaries to your documentation system
- • Create cheat sheets for ongoing projects
- • Export important conversations
- • Store outputs in searchable formats
📁 Organize Projects
- • Create dedicated projects for different work areas
- • Add brand guidelines, style guides, reference docs
- • Set specific instructions per project
- • Keep personal and professional work separate
🔄 Maintain & Update
- • Update documentation as projects evolve
- • Refresh context when performance degrades
- • Delete old attachments, add new ones
- • Treat it as living documentation
Key Quotes
"It's like I'm calling into tech support or calling into a bank customer service and I've spent minutes explaining what's going on and my problem, and then I have to talk to someone new."
— Bert Carroll on context windows
"AI is great, but I do think this is score one for the humans. A human who is coding or creating the code sitting there for a couple hours is going to remember what was built on."
— Julianna Fricchione
"Every time you talk to a new AI, it's like talking to a totally new one. It's bringing a new intern and then you start from scratch."
— Bert Carroll
"If you just, if you didn't delete it or file it from the very beginning when email first started, it's gonna wreak havoc. Same thing with AI conversations."
— Julianna Fricchione
"I'm glad that it drops context 'cause the new bot... I fired Grok once because it worked me into a corner I didn't like."
— Bert Carroll
"As your project evolves, it's naturally gonna evolve as it adds complexity. So you're continually documenting it and that will help you deal with it when it gets to the point where you need to start over."
— Bert Carroll
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