If you're thinking about where to look, you're probably thinking too much. Although It normally makes me more comfortable to look at my board, with quick glances at where I'm goin, I guess.
Don't think; feel! Worked for Bruce Lee.
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Depends on where this hill is located, I'm not goin down no main road the traffic will be fucked. Anywhere else hell ya I'd send it. Fuck it, just run out if it gets hectic.
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For ankles you can do this thing I do sometimes. Stand on a curb / step / wall with ur heel hanging off, then slowly slowly lower your heel down further and further. You're trying to kinda stand vertically on the wall of whatever you're standing on. Reaaaallllyyyy stretches it. And then put your heel on the curb and try to lower your toes so you're standing vertical backwards. Always helped me.