Long Planning Sessions Don't Lose Their Shape Anymore

A 14-day Japan trip takes about 90 messages to plan properly. Somewhere around message 60 — usually after you've settled the ryokan in Hakone, traded a Kyoto temple-marathon for one slow morning at Tofuku-ji, and accepted that the Tsumago-Magome walk is worth the train day — the planner used to forget that you'd said, on message 4, that your partner doesn't eat shellfish. By the time it recommended an omakase counter in Kanazawa, it was guessing again.

The problem isn't that long sessions are rare. They're the work. A real itinerary for two travelers across two weeks needs a brief, a critique of that brief, three rounds of pacing trade-offs, a couple of rerouted days, hotel choices that depend on those routes, and food the planner actually believes in. The shorter the chat, the less Fortrip is doing for you. The sessions where context loss hurts most are exactly the sessions worth having.

We rewrote how the chat is held in memory. Every Fortrip agent now compacts as the chat grows, and the rules for what to compact are written specifically for trip planning. We keep the things that decide the next message: the traveler profile (who's going, what they don't eat, how they like to move), the hard constraints (dates, budget, mobility, no red-eyes), the pacing decisions you've already made (one city per three days, no museums after lunch), and the choices that are now load-bearing: the hotel you picked, the day you flipped Kyoto and Osaka, the half-day you carved out for Naoshima. Those are the spine of the trip. They don't get to drift.

What we let go is everything that was useful once and isn't anymore. The early scaffolding where you and the planner were still circling the shape of the trip. The five hotels you considered in Hakone before you picked the sixth. The Hokkaido detour you talked yourselves out of on message 30. The aside about whether to fly into Haneda or Narita, settled two hours ago. Those exchanges did their job. Carrying them forward as raw text only crowds out the things that still matter. So we summarize them — briefly, faithfully — and move on.

The judgment about what's load-bearing and what's exhaust is the part you can't buy off the shelf. A generic version of this would drop your shellfish allergy and keep the small talk. Ours is tuned in the other direction: constraints and decisions are sticky, exploration is compressible, the trip's spine is protected. We'd rather forget which adjective you used about a hotel than forget that you booked it.

You will mostly notice this in the negative. Plans no longer wobble in the second half. The validator stops re-asking what you already told us. Day 11 of a 14-day trip comes back consistent with day 2. The longer the session, the more the difference shows.