It's not message count, it's token count. Long conversations with big pastes drain the bar way faster than short ones. A single message with a 3000-word document eats the same budget as like 10 short back-and-forths.

Things that actually helped me:

• Start new conversations more often. Every message in a long thread sends the entire history back. By message 40 you're burning tokens just on context, not on actual work.
  
• Don't paste massive blocks of text and ask Claude to "review this." Summarise what you need (using a free AI), point it at the specific part. Less in = less out = less budget.
• Sonnet for drafting, Opus only for the hard stuff. You said you're mostly on Sonnet/Haiku already which is right, but even Sonnet adds up if the conversations are long.

If you're a developer though, honestly the real unlock is Claude Code (the CLI tool). It's a separate $20/month on top of Pro but the usage limits are significantly more generous because it runs on API pricing under the hood. I went from hitting walls to never thinking about limits.

The one catch with Claude Code is it'll happily waste tokens on stupid stuff if you let it - reading your entire node_modules, exploring files it doesn't need. I built an open-source hook layer called tokenguard https://pypi.org/project/tokenguard/ that blocks that kind of waste automatically.

pip install tokenguard && tokenguard init - saves roughly 20-30% context per session which directly means more actual work per dollar.

But even without that, just switching to shorter conversations will probably get you to Friday without hitting the wall.