Modify: What most people do is modify the advanced exercises so they have a version of the exercise that is easier but still challenging to them. When you modify an exercise you want to think about the intent of the exercise and do something similar. For example, swan dive is an advanced back extension (backward bending) exercise. We build up to swan dive with swan prep which is a small lift of the upper back away from the mat lightly supported by the hands. Similarly, jack knife can become a shoulder stand supported by the hands. Shoulder bridge, an int./adv. exercise which has you kick one leg up and down while in a bridge position, could become an exercise where you just hold the bridge and take one foot off the mat for a moment. And, yes, you can use your hands for help almost all the way through the roll up. Most Pilates exercises can be simplified in this way.
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Build Up:The most long term benefits of Pilates come to those who build their practice on strong fundamentals. So another way to work toward advanced exercises is to think to yourself: What's in the way? What kind of strength or flexibility do I need to be able to do this exercise? Then focus on exercises that help you build those qualities. Let's continue with shoulder bridge as an example. If you look at the shoulder bridge instructions you are going to find out that hamstrings and inner thighs have to work very hard in this exercise, especially when a foot comes off the floor. So you might modify it as we talked about above. And you might do exercises that look quite different than shoulder bridge but build the inner thigh and hamstring strength that you need. Similarly, shoulder bridge makes you open the front of your hip. How about a hip opening stretch like a standing lunge? It doesn't look like shoulder bridge but it builds toward it.
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Challenge Yourself: For our third key, I want to say that while the most important thing is to do a balanced routine, building up to advanced exercises safely, there does come a time when you have to take a chance on something and go for it. Sometimes you have to play along the edges of an exercise for a while. Go a little further than you thought you could. If you shake, or look goofy, that's OK. Just remember, advancing is always your call - not your teachers or what's next on a program. But don't get stuck thinking you can't do an exercise when you can take a next step toward it.
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