A very good rule to follow here is the "80% rule". This simply means that you should never discharge a LiPo pack down past 80% of it's capacity to be safe. For example, if you have a 2000 mAh LiPo pack, you should never draw more than 1600 mAh out of the pack (80% x 2000). This is assuming a healthy pack as well that has the full 2000 mAh capacity (as packs age, their capacity drops).
This again is where computerized chargers pay for themselves many times over so you can see how much capacity the battery takes allowing you to adjust your flight times accordingly to stay within that 80% rule to get the most life out of your pack.
If you don't have a computerized charger to confirm the amount of capacity, another good indicator is to measure the open circuit voltage (no load voltage) of the pack or individual cells after a flight/drive with a digital volt meter or other similar digital device. An 80% discharged LiPo cell, will give an approximate open circuit voltage of 3.73 to 3.75 volts. A 3S LiPo pack therefore would show about 11.19 to 11.25 volts after a flight when it's 80% discharged, a 6S pack would be about 22.44 volts.