CHRISTINE Never Lose Good Work to a Full Chat Again
The Checkpoint captures everything that matters — the decisions, the progress, the context, and the single next move — into one copy-paste block, so you can open a fresh conversation and pick up exactly where you left off. Zero loss.
← Back to the Skills LibraryInstalled in under a minute. No tech skills required.
You don't need to know how to code, and you don't need to set anything up. There are two blocks below. If you can copy and paste, you can install this.
Paste the instruction
Copy the first block and paste it into a brand-new Claude conversation. Don't hit send yet — it's the note that tells Claude what to do.
Paste the skill underneath, then send
Copy the full skill block and paste it right below the instruction. Send it. Claude builds the skill, personalizes it to your business, and confirms when it's ready.
Install the skill below for me. Keep the skill text exactly as written, then personalize its defaults from what you already know about me — my business, my voice, my priorities, and the places I keep my notes and files. Confirm when it's installed and show me exactly how to run it.
--- name: checkpoint description: Save my work before the chat compacts and hand it off clean to a new conversation. Use whenever I say "checkpoint," "checkpoint and handoff," "save this," "save my progress," "hand this off," "this is getting slow," "it's compacting," or any time I'm about to lose where I am. Also suggest it when we're past 20 exchanges or when I'm about to start something new inside a long thread. --- # The Checkpoint Every chat is a whiteboard. Blank when it starts, and it fills as we create. Around 80 to 90 percent full, the conversation compacts and good work gets lost in the summary. This skill captures everything that matters into one block I copy into a fresh chat so I pick up exactly where I left off. Zero loss. Two parts, always delivered together. The Checkpoint captures where the work stands. The Handoff is the block that loads it into the new chat. ## When To Run It - The chat is getting slow. That lag is the whiteboard filling up. - The conversation starts compacting. Do not keep working in a compacting chat. - Around 20 back-and-forth exchanges deep. That is the awareness trigger. - I am about to start a new phase inside a long thread. New phase, new whiteboard. - I am wrapping up for the day and want to continue clean tomorrow. ## Process Step 1 — Read the whole conversation. Pull everything the next chat needs to keep going. Miss nothing that would be expensive to rebuild. Step 2 — Capture the state. What we are working on, decisions made and why, what is done, where things stand, what is left in priority order, the context that is hard to reconstruct, anything referenced, and the single next move. Step 3 — Deliver one clean handoff block in the format below. Copy-paste ready. This is the whole point, so it has to be something I grab in one motion. Step 4 — Tell me what to do. Copy the block, open a fresh chat, paste it, say "load this checkpoint and pick up from The Next Move." ## The Handoff Format CHECKPOINT AND HANDOFF Date and version (V1, V2, V3) Session focus, one line What We Are Working On — the project and the goal in one or two sentences Decisions Made — each call that got locked in, with the reason behind it What Is Done — specific things created, written, built, or finished Where Things Stand — what works, what is half-built, current state of play What Is Left To Do — remaining work in the order it should be tackled Important Context — preferences, constraints, naming conventions, requirements, gotchas discovered along the way Referenced — links, files, documents, and sources that matter The Next Move — the single first thing the new chat should do Close with the resume line: open a new chat, paste this block, say "load this checkpoint and pick up from The Next Move." ## Loading A Handoff When I paste a checkpoint block into a new chat, read the whole thing, give me a two-line recap so I know you have the full picture, confirm what is left and ask if anything changed, then start on The Next Move. ## Naming Convention Name chats V1, V2, V3. Checkpointing out of V1 into a new chat makes that chat V2. Each version is a phase, so I always know where I am and where to find things. ## Standing Rules - A checkpoint saves the chat. A second brain saves everything. When we build something worth keeping, remind me to send it out of the chat and into my second brain so it lives somewhere real. - Specific beats vague. Real names, real decisions, real next steps. - Capture the why behind decisions, not just the what. - Scannable is the standard. Someone loading this gets up to speed in under two minutes. - If we are past 20 exchanges and no checkpoint has run, say so without waiting to be asked.
From then on, when a chat gets long or slow, just say "Checkpoint and handoff."
Want to go further than skills?
Skills like this are how Christine runs her own business every day. In the Heart-Led AI Signature Group Coaching, she teaches you the whole system — live, in plain English, at your pace.
Explore Signature CoachingOne handoff block. Everything the next chat needs.
Say the word and you get back a clean, copy-paste-ready block — not a fuzzy summary. These are the labeled sections of the real handoff, every time:
1 · What We Are Working On
The project and the goal in one or two sentences — so the new chat knows exactly what game it's playing.
2 · Decisions Made
Every call that got locked in, each with the reason behind it — so nothing gets relitigated in the next conversation.
3 · What Is Done
The specific things created, written, built, or finished. Real names, not vague gestures.
4 · Where Things Stand
What works, what's half-built, and the honest current state of play.
5 · What Is Left To Do
The remaining work, listed in the order it should be tackled.
6 · Important Context
Preferences, constraints, naming conventions, requirements, and the gotchas discovered along the way — the stuff that's expensive to rebuild.
7 · Referenced — plus The Next Move
Every link, file, and source that matters, then the single first thing the new chat should do. The block opens with a date, a version number, and a one-line session focus — and closes with the exact resume line to say in the fresh chat.
And it speaks up before you ask
Past about 20 back-and-forth exchanges with no checkpoint, the skill says so on its own — you don't have to remember to remember. One more standing rule worth knowing: a checkpoint saves the chat, but a second brain saves everything. When you build something worth keeping, it reminds you to move it out of the conversation and into your second brain, so it lives somewhere real.
Keep stacking: pairs beautifully with Session Close
The Checkpoint rescues a single conversation mid-stream so no work gets lost — Session Close wraps up your whole working session, updating your core files so tomorrow-you has somewhere to land.
Get Session Close →Because every chat is a whiteboard.
It starts blank and fills as you create. Around 80 to 90 percent full, the conversation compacts — and good work gets lost in the summary. The Checkpoint exists so a full whiteboard never costs you the work on it.
It reads the whole conversation, not the last page
Before writing anything, the skill pulls everything the next chat needs to keep going — with one standard: miss nothing that would be expensive to rebuild. That's a much higher bar than a quick recap.
It captures the why, not just the what
Decisions come with the reasons behind them, so the new chat doesn't reopen debates you already settled. Specific beats vague: real names, real decisions, real next steps.
One block, one motion
The whole point is a handoff you can grab in a single copy-paste. Scannable is the standard — anyone loading it gets up to speed in under two minutes.
Loading is built in
Paste the block into a fresh chat and the skill reads it all, gives you a two-line recap so you know it has the full picture, confirms what's left and asks if anything changed — then starts on The Next Move.
V1, V2, V3 keeps you oriented
Checkpointing out of one chat makes the next chat the next version, and each version is a phase. You always know where you are and where to find things.