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Today I jumped 13'6 using a 13'6 160 holding about 13'3, but last week i jumped 13'6 using a 14' 155 holding about 13.

the 14' foot pole was equivalent to a 13' 175 with the whole 20lb a foot rule and the 13'6 was about a 13'3 165.

when using the 14' i had the standards on 16in and when using the 13'6 they were on 28in

my question here is, should I keep the lower hand hold of about 13' and continue to increase the stiffness of my poles, or should i stay with about 160-165lb of stiffness and move up to the top of a longer pole?

by the way im 5'5 140lb

(It's about 18 pounds per foot.) Depends on how deep you're landing in the pad and how good your swing is. If your swing isn't so great but you're landing pretty deep, then you might want to consider moving your grip up. If your swing is too powerful for the pole you're using (I seriously doubt) then you should increase the weight rating.

If you can safely rotate a longer pole (higher grip) to vertical, then I would continue to strive towards moving the grip up. However, anytime the standards are at 16in they are too close, imo.

It's hard to say without seeing you vault, but I would suggest staying on the shorter pole until the transition to a longer pole would have the same "relative" stiffness. 13'3" 165 to 13' 175 is a sizeable transition.

Possible pole selections would be a 13'6" 165 or a 14' 150. If you've got them or can trade for them, great! Move your current grip to the 14' 150, then with every vault you land deeply in the pits, move your grip up. Soon you should be near the top of the larger pole and effectively using your new grip. If you don't have the poles, keep working on your takeoff with the smaller pole until you can set the standards at (at least) 24in on that 14 footer you've got.

Good luck!