Don't upgrade to the $100 Claude plan (yet).

These 21 hacks make the $20/month plan enough:

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1. You upload PDFs raw. One page = 3,000 tokens.

Fix: Paste the text into a Google doc. Download as .md format. Under 200 tokens.

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2. You build files inside Cowork too early.

Fix: Plan in Chat first. Move to Cowork only when you know exactly what you want.

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3. You write 500-word prompts that reload.

Fix: Write 29 words instead:

I want to [task] to [goal]. Ask me questions using AskUserQuestion.

4. You say "redo the whole thing" to fix section 3.

Fix:

Only redo section 3. Keep everything else. No commentary. Just the output.

5. You send 3 separate messages for 3 tasks.

Fix: One message, three tasks.

Summarize this, list the points, suggest a headline.

6. You type "No, I meant," stacking on the history.

Fix: Click 'Edit' on your original message. Fix it. Regenerate.

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7. You rewrite prompts from scratch every time.

Fix: Keep a prompt library. Same structure, swap the variable.

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8. You use Opus for a simple grammar check.

Fix: Sonnet for quick tasks. Save Opus + Extended Thinking for deep work.

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9. Your about-me file is 22,000 words (too long).

Fix: Trim to under 2,000 words. End sessions with

Write a session-notes .md.

Paste my .md file prompt: ruben.substack.com/p/yo…

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10. You never restart & keep stacking long chats.

Fix: When Cowork goes sideways, click "Restart the conversation from here" on an earlier message.

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11. You never summarize before things get long.

Fix: Every 15-20 messages → summarize, copy the brief, start a fresh session.

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12. You use Projects for recurring files.

Fix: Use Projects. Upload once. Every chat inside references it without re-burning tokens.

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13. You dump 50 files into Cowork "just in case."

Fix: Only include what this task needs. Zero folders for quick tasks like email drafts.

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14. You keep 3 topics in 1 chat. Claude re-reads all.

Fix: New topic = new chat. Always. Dead context is dead tokens.

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15. You leave search & connectors on by default.

Fix: Default everything off. Turn features on per task, not per account.

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16. You manually run the same report every week.

Fix: Use /schedule.

Every Monday at 7am, create my weekly briefing.

17. You let Claude Code explore your whole repo.

Fix: Be specific.

Build a bar chart from this CSV. Save as chart .png.

18. You skip Personal Preferences & waste setup.

Fix: Settings → Personal Preferences. Set your tone and style once.

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19. You type lazy prompts like "make it better."

Fix: Speak your prompts with wispr .ai. Richer context in one shot.

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20. You burn your whole limit in one morning.

Fix: Claude runs on a rolling 5-hour window. Split it.

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21. You use Claude for things it can't do.

Fix: Know your tools. Images → Gemini.

Real-time search → Grok.

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To download my exact .md files:

1. Go to how-to-ai.guide.

2. Subscribe for free. Open my welcome email.

3. Hit the automatic reply button inside.

4. Go to the Notion link in the second mail.

5. Copy-paste prompts, too.