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One of the most important judgment calls in agentic coding is knowing when to keep working in the current conversation versus starting fresh. Both choices have trade-offs, and the right answer depends on your situation.

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Consider Starting Fresh When:

  • You have made multiple major changes without progress
  • The codebase has become overly complex due to accumulated fixes and workarounds
  • You have gained insights that suggest a fundamentally different approach
  • The conversation has grown very long and credit cost per message is increasing
  • Workshop seems confused by conflicting instructions from earlier in the conversation
We've tried patching this approach several times, but I think we
need to reconsider our basic architecture. Let's start fresh with
what we've learned.
When starting a new conversation for an existing project, bring key context forward: 
This is an existing [type of project] that does [main functionality].
Look around the project directory to understand the current
implementation, then help me add [new feature].

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Persist When:

  • You are making incremental progress, even if it is slow
  • The issues are specific and isolated rather than systemic
  • You have a clear debugging path to follow
  • Workshop has built up useful context about your project that would be expensive to recreate
  • You are close to a solution and just need a few more iterations
We're getting closer. The authentication flow is almost working,
and I think we just need to fix the token refresh logic.

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The /compact Command: A Middle Ground

When your conversation is getting long but you are not ready to start fresh, the /compact command offers a middle ground. It summarizes the conversation to reduce context size while preserving key information. Use /compact when:
  • The conversation is long and you notice credit costs increasing
  • You want to continue the current line of work but shed irrelevant earlier context
  • You have completed one phase of work and are moving to a new phase within the same project

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Decision Framework

Ask yourself these questions:
Approach problems (wrong architecture, wrong library, wrong pattern) are better solved by starting fresh with a new plan. Execution problems (a specific bug, a missing feature, a configuration issue) are better solved by persisting.
If Workshop has built up significant understanding of your codebase, starting fresh means it has to re-learn that context. If the conversation is mostly failed attempts, starting fresh costs you very little.
Credit cost per message increases with conversation length. If you are spending more credits on context than on useful work, it is time to start fresh or use /compact.
If Workshop is making suggestions that contradict earlier decisions or referencing files that no longer exist in their current form, the conversation context may be doing more harm than good.

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Signs You Should Start Fresh

  • Workshop keeps suggesting the same fix you have already tried
  • The conversation has accumulated contradictory instructions
  • You realize the initial approach was wrong and need to go in a different direction
  • You are spending more time explaining the conversation history than making progress
  • Error messages are piling up and Workshop seems to be going in circles

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How to Start Fresh Effectively

  1. Save your progress — Commit any working code before starting a new conversation
  2. Note what you learned — Write down the key insights and failed approaches
  3. Update .memex/rules.md — Add any new constraints or decisions to your project rules
  4. Start with context — Give the new conversation a concise summary of the project and what you want to accomplish
  5. Reference specific files — Point Workshop to the relevant parts of your codebase rather than expecting it to discover everything
I'm building a task management app with React and Supabase.
The authentication is working but I'm having trouble with
real-time subscriptions. Check src/hooks/useRealtimeSync.ts
for the current implementation. The issue is that updates
from other users aren't appearing without a page refresh.

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Best Practices for Multi-Conversation Projects

For projects that span many conversations:
  • Keep .memex/rules.md up to date — This is the persistent memory across conversations
  • Commit at milestones — Every working state should be a git commit
  • Use descriptive commit messages — They help Workshop (and you) understand project history
  • Document decisions — Add notes about why you chose certain approaches, not just what you built
  • Start each conversation with orientation — Give Workshop a brief tour of the current state before diving in