1) If you are properly warmed up
2) If you are wearing non-restrictive clothing
3) You're on even, non-slippery ground
4) You're wearing footwear that allows you to keep your footing yet rotate on your supporting foot
5) Your opponent is in range
High kicks can be spectacularly effective - in the ring. In a self-defence situation you're more likely to be ambushed. Your opponent is more likely to be beyond the inside range of your kicks and pressing the attack.
The bottom line is that high kicks are low percentage - too risky to use in situations where the worst case scenario is death or serious injury.
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"It was about that time I realized that searching was my symbol, the emblem of those who go out at night with nothing in mind, the motives of a destroyer of compasses." -Cortázar
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