I achieved the pistol squat on my left leg after 0.5 years of training!

@omnitude In addition to flexibility, make sure you're using good squat form.

I was having go impingement and dorsiflexion issues until I went back and refreshed my squat form as demonstrated by Mark Rippetoe.

Make sure your feet and knees aren't turned too far inward, and make sure you're getting your hips back. Pistol squats require more dorsiflexion for balance, but regular squatting shouldn't require very much.
 
@jarend89 Yes, classic calf stretching works for me. After I run, my calves get a bit tight, and I notice that I tend to fall backwards doing the pistol. Stretching corrects this immediately.
 
@frogs_are_neat I think you should be capable of both. I am, but I think pistols are somewhat of a novelty when building muscle is a primary goal. I kinda forget that people have different goals than me though so that's my bad. They are fun to do.
 
@lorinczpam I don't really have the whole program just a torrented PDF that includes the workouts. It's ok, but some of the workouts i feel aren't rigorous enough. I dont feel drained always at the end. like the progressions to one arm pushup are cool, and my L-sit hold has improved a lot but its like an 8-step program, once you hit step 4, they require the muscleup, and step 7 or so, front lever is included. these are workouts that take time and other exercises outside of the program to be able to do. So it can be confusing if you want to stick to a strict routine. Still trying to find an ideal blend of weights and bodyweight, just combining this one and the kinobody warrior shredding program at the moment.
 
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