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When you want to execute a Heelside 360, cut outside of the wake just enough so that you can take a relaxed cut in to clear both wakes. Keep your knees bent a bit, keep the handle in tight, and take a nice, slow progressive edge to the wake. After you wait for a good pop off the wake by standing tall, keep the handle in tight and begin to rotate by pulling the handle to the small of your back. Besides getting a good pop, waiting will help you stay on axis in the air. As you're making the handle pass focus on keeping the handle in tight to your body, and don't let go with your back hand until your front hand has the handle again. Keep your head up, and shoulders on axis. After passing the handle, start turning your head to look for your landing. You've passed the handle and have spotted your landing on the downside of the second wake, so now it's just easy from here. Keep your head up, bend your knees, and keep the handle in tight so it doesn't jerk when it tightens up again when you land. That doesn't look stylish when that happens.