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Leaving leftover chili to cool on the counter is generally not recommended due to food safety concerns. When food is allowed to cool at room temperature, it stays within the temperature range where bacteria can multiply rapidly, increasing the risk of foodborne illness.

To cool leftover chili safely, it is advisable to follow proper food handling guidelines:

1. Refrigerate Promptly: Once the chili is cooked and you're finished serving, refrigerate any leftovers promptly. Ideally, food should be refrigerated within 2 hours, or 1 hour if the ambient temperature is above 90°F (32°C).

2. Divide into Smaller Portions: To facilitate faster and more even cooling, divide large quantities of leftover chili into smaller, shallow containers.

3. Use the Two-Hour Rule: If chili (or any perishable food) has been left at room temperature for more than two hours (or one hour in temperatures above 90°F), it is safer to discard it to avoid the risk of bacterial growth.

Remember that proper food safety practices are crucial to prevent foodborne illnesses and ensure the health of those consuming the food.