I'm not an instructor, so I don't have a very good response to this, but I have some thoughts.
Firstly, I also have to kind of rock back into Plow. Not too dramatically, but I don't get into it with total ease. However, once I am *in* Plow, there seems to be a natural flow to Shoulder Stand. In Plow, you should already have your hips more or less in the right place relative to your shoulders, so then the trick is lifting your legs. Which, btw, is also not so easy for me, exactly. I always enter Shoudler Stand by way of Half Shoudler Stand - that sort of sitting in an upside down chair position. I get my balance there, then extend my legs.
So maybe the key for you might be to focus on getting a good mastery of Plow? Using the strength of your legs to help pull and lift your torso into the right position?
That may not be incredibly helpful, but it's the best insight I can offer. Hopefully someone else will have more.
Funnily, my problem is sometimes getting *out* of Plow gracefully. You're supposed to grab your feet and roll down one vertebrae at a time, but sometimes I sort of get stuck, and can't get the rolldown started without a big flop.
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Firstly, I also have to kind of rock back into Plow. Not too dramatically, but I don't get into it with total ease. However, once I am *in* Plow, there seems to be a natural flow to Shoulder Stand. In Plow, you should already have your hips more or less in the right place relative to your shoulders, so then the trick is lifting your legs. Which, btw, is also not so easy for me, exactly. I always enter Shoudler Stand by way of Half Shoudler Stand - that sort of sitting in an upside down chair position. I get my balance there, then extend my legs.
So maybe the key for you might be to focus on getting a good mastery of Plow? Using the strength of your legs to help pull and lift your torso into the right position?
That may not be incredibly helpful, but it's the best insight I can offer. Hopefully someone else will have more.
Funnily, my problem is sometimes getting *out* of Plow gracefully. You're supposed to grab your feet and roll down one vertebrae at a time, but sometimes I sort of get stuck, and can't get the rolldown started without a big flop.