Build a one-day itinerary that respects every hard constraint

About this exercise

Plan your executive's Thursday in Chicago as a plain-text itinerary, one line per item with a start time like 08:30, in time order. Respect every fixed time, travel time and buffer in the notes, end with the flight, and add a final line starting "Flag:" naming any constraint that cannot be met. Do not invent bookings or times not implied by the notes.

Common mistakes when you ask AI for this

• Using the old meeting time. The AI plans around 10:30. Try: Say: "The customer meeting moved to 10:00."
• Ignoring the travel math. The AI forgets the drive and the 90-minute airport rule. Try: Say: "Work backward from the 18:10 flight: 90 min early plus travel plus traffic."
• Missing a required item. The AI skips lunch or the buffer. Try: Say: "Include lunch (40 min) and the 30-minute buffer."
• No flag line. The AI hides a conflict. Try: Say: "End with a Flag: line naming any constraint that cannot be met."
• Markdown. The AI makes a bold table. Try: Say: "Plain text, one line per item."
• Trusting the AI to count words. AI is bad at counting. Ask for a total word limit and it often lands over it. Try: Cap each line: "each line under 14 words."
• Trusting the AI to count words. AI is bad at counting. Ask for a total word limit and it often lands over it. Try: Cap each part instead, for example: "each line under 12 words."

What a strong prompt includes

• Time format
• Work backward
• Hard constraints
• Flag line
• Plain text

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