Before trying handstand push-ups, master the pike push-up and 90 degree push-up.
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When you've mastered the floor push-up and the pike push-up, you may want to move onto something even more challenging that can help you train for the mother of all push-ups: handstand push-ups. To get there, start with the 90 degree push-up, in which your feet are elevated to create a 90-degree angle between your upper and lower body. Any standard push-up requires a good deal of shoulder strength, but the 90 degree push-up requires more than most.
Place a bench, high chair, wooden box or another type of solid object with a flat surface on the floor, leaving at least 4 feet of open space on all sides. The bench should be roughly half your height. If you fall, you'll want plenty of room so that you won't land on something or knock over the bench and possibly sustain a serious injury.
Stand with your body facing away from the bench, positioning yourself about 3 feet from the bench.
Place your hands flat on the floor about shoulder-width apart.
Place your feet on the bench, and then walk your feet and hands backward to position your trunk perpendicular to the floor, with your hips above your head, your head between your hands and your legs at approximately a 90-degree angle from your trunk. It may help to have a friend look at your position and ensure your body is at an approximately 90-degree angle.
Keep your knees straight and your toes pressing into the bench. Push into your hands to straighten your trunk.
Lower your head slowly, making sure you remain in control of your body, until your head touches the floor or your hair grazes it. Work to point your elbows in toward the bench slightly, instead of flaring them out to the sides. If you flare them out, the exercise becomes more of a military press. That's still a good workout for your shoulders, but it won't do much to help you practice the stability you'll need to perform a full handstand push-up.
Press into the floor with your hands and then use the strength of your shoulders and core to move back to the starting position. If you can perform another repetition safely, do so; the goal is to be able to repeat the entire move 8 to 12 times.
Don't try this exercise if you haven't mastered performing sets of at least 10 to 20 standard, on-the-floor push-ups. Not having the upper body strength required for this exercise is likely to result in serious injury. If you need another type of progression between the 90 degree push-up and the standard push-up, try pikes on the floor. Start with your legs on the floor in a 90-degree pike position, similar to the "downward dog" in yoga. Then lower your body until your forehead nearly touches the floor and push back up to the starting position.
Whatever type of bench or support you use, make sure it's stable and weighs a significant amount; lightweight chairs will be more likely to tip over when you start moving around, which also can lead to serious injury.