Series: Weekend at Claude's — misadventures in building a production app with an AI anyone could mistake for the person who's going to make the whole thing happen
Claude has no memory between sessions. Every conversation starts completely fresh.
In the movie, Bernie's friends spent a whole weekend pretending nothing had changed. I have to actually brief my collaborator from scratch every single time we meet. It's less cinematic, but the principle is similar: someone has to remember what's going on, and it's going to have to be me.
My solution is a living TASKS.md file that I maintain in the repo and upload at the start of every session. Claude reads it, orients itself, tells me where things stand and what to work on next, and we get going. The re-introduction takes about thirty seconds instead of twenty minutes.
The format is simple. Two workstreams: A for build tasks (Claude Code's domain) and B for business tasks (mine). Each is a table with four status values — [ ] not started, [~] in progress, [x] done, [!] blocked — plus a blocker column so dependency order is explicit. Every task has an owner.
The session kickoff prompt is three lines:
Starting a new Aphilaty session. Uploading current project files now. Please wait for all uploads before responding. Session kickoff — please review TASKS.md and tell me where we are and what to work on.
Claude reads the file and gives me a clear picture: what's ready, what's blocked, what the highest-value next task is. Then we work.
A few things I've learned keeping this up:
Keep it honest. A stale task list is worse than no task list — you'll start something that's blocked or skip something that's ready. Update it before each session, not after.
Two workstreams matter. Build tasks and business tasks move on completely different timelines with completely different owners. Mixing them makes both harder to track.
Blockers are first-class. The blocker column isn't documentation. It determines what you can actually start. Claude uses it to tell you what's actionable right now.
It's a simple system. For a solo founder context-switching between product, legal, business, and multiple AI tools — building in spare hours around a day job, not full-time — simple and consistent is everything. I can pick this up on a Tuesday night after a gap of three days and be productive inside thirty seconds. That's not an accident. That's the system working.
Bernie never knew what was happening either. At least I have a spreadsheet.
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