When the trip is people coming to you.
Trip Planning was for when you're going somewhere. This lesson is for when people are coming to you — Thanksgiving you're hosting, Christmas at your house, a big birthday party, in-laws staying for a week. Different problem shape: you're managing the home, the food, the timing, the kids, and the guests' experience all at once.
Same temporary-Project pattern, applied to hosting. Cowork builds the menu, the prep timeline, the day-of choreography, and the "what could go wrong" map.
The menu and the prep timeline.
Use Thanksgiving as the worked example — same shape works for any big-meal hosting event. Open your temporary Project (the one you built in Build a Temporary Project, named something like "Holiday — Thanksgiving 2026 at our house").
One way to ask:
Sample — menu and prep timeline
Build me a full menu and prep timeline for this hosting event. Use the Event Reference for guest count, dietary specifics, and any guest preferences. Include:
1. The full menu with rough portion estimates so I know what amounts to buy.
2. A complete grocery list, organized by aisle (use the same format as my Meal Planning Deep Dive grocery lists).
3. A prep timeline starting [X] days out, working backwards to the day-of. Cover: when to defrost the turkey, when to make pie crust, when to prep stuffing, when to set the table, anything that can be done ahead.
4. A day-of cooking timeline: hour by hour, what's in the oven, what's on the stove, when sides need to be plated.
5. The timing-coordination layer: when each thing actually hits the table at the right temperature, so the gravy isn't congealing while I'm still mashing potatoes.
Save the menu as Menu.md, the prep timeline as Prep-Timeline.md, the grocery list as Grocery-List.md, and the day-of cooking timeline as Day-Of-Cooking.md.
Cowork builds all four files. Skim them. The day-of cooking timeline especially — make sure it matches the realities of your oven (single oven vs. double, when something else needs the burner, etc.). Iterate on anything that doesn't fit your setup.
Day-of choreography + the "what could go wrong" map.
The food timeline is one layer. Everything else — getting the house ready, kids dressed, drinks chilled, table set, guests arriving — is the other. Cowork builds both, plus a short list of the most likely places things break down so you can plan around them.
One way to ask:
Sample — day-of choreography
For the day itself, build me a Day-Of Choreography file. Hour by hour from when I wake up to when guests sit down at the table. Cover: who's responsible for what (me, [partner if relevant], kids old enough to help — pull ages from my Family Factsheet), the easy-to-miss things (chilling drinks, setting the table, finishing decorations, getting kids ready, taking out the trash, having a clean bathroom guests will actually use), and built-in buffer time so I'm not running the whole day.
Plan for [X] guests arriving at [time]. Save as Day-Of-Choreography.md.
Then run the "what could go wrong" pass:
Sample — anticipate the breakdown points
Walk me through the things most likely to go wrong on this day, given our specific setup (single oven, [number of] kids, the menu we're making, the guests arriving). For each one: what tends to happen, when it'd happen on the timeline, and what to do ahead of time to prevent or absorb it. Don't list everything possible — focus on the three or four most likely.
Print the day-of stuff.
Same approach as the morning-of script from Trip Planning. Day-of choreography and the cooking timeline are both worth printing the night before — tape them inside a cabinet door where you can glance without unlocking your phone. Tell Cowork: "reformat the day-of files for letter-size paper with bigger fonts."
The multi-day houseguest variant.
Same pattern, different problem shape. In-laws staying for a week. College friend visiting through the long weekend. Anyone where the hosting stretches across multiple days and meals.
One way to ask:
Sample — multi-day houseguests
My [in-laws / friend / etc.] are staying with us from [dates]. Build me a hosting plan. Cover:
1. A few key meals over the visit they'd enjoy. Use the Event Reference for any dietary specifics, and my Family Factsheet for what my kids will eat (so I'm not cooking two completely separate meals every night).
2. A "do-ahead" list — what to prep before they arrive so the first day isn't exhausting.
3. A "guest-ready" checklist for the house: clean towels, room set up, what they might need (chargers, hairdryer, water bottle by the bed, anything else).
4. A few ideas for outings or activities that fit their pace and interests — not overscheduled, and including some downtime where everyone can just be in the house separately.
5. The realistic version: where in this visit am I most likely to hit my own wall, and how do I plan a small break in for me?
Save as Houseguest-Plan.md.
Don't overschedule.
The lesson tucked in there — "everyone needs downtime" — is the one most hosts forget. Cowork can build you a packed itinerary, but if you ask it to, it'll also build you a saner one. Tell it: "plan around the assumption that we'll all need a break at some point each day. Build in two-hour windows where nothing is scheduled."
Next: Debrief & Archive.
Last lesson of the module — and the last lesson of any temporary Project. When the event is over: capture what worked, what didn't, what you'd do differently next time. Then archive the Project cleanly so it doesn't sit around as noise.
Continue to Debrief & Archive →