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Upwind - If the wave coming towards you is going to break significantly as you go into it, you probably want to be stroking with a blade in the water applying power as the wave hits you. Beyond providing greater stability and reducing the amount you stall, this is also better than holding your paddle horizontal trying to keep it above the wave. If you have your paddle horizontal and the wave still catches your paddle you stand a pretty good chance of getting smacked by your paddle.
When paddling steadily upwind, experiment with your cadence. Slowing your stroke down somewhat may allow you to more easily adjust with a faster or slower stroke to time with the waves and insure a solid catch. Try to resist any inclination to brace as much as possible and just rely on the support you get from a solid catch. Also try to sense both of your heels and the pressure you should be feeling from each heel from each stroke on the same side as the pressing heel. Make sure you are not getting stuck with pressure on one heel/side (particularly when turning) which can also lock in a tilt to your ski to one side. Practice maintaining all of this feel and synchronized leg thrust as you make turns going from upwind to downwind and vice versa.
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Powering Through A Columbia River Gorge Wave
Gorge SIC Race Practice 2019 Photo by: Wilson Reavley - Click to enlarge
Advancing to Rougher Conditions and Stronger Downwind Paddling
Practice/Evaluation Discussion
When Are Conditions Too Rough?
This can be a question of too rough for anyone(?) and it is also a question of the combination of how rough conditions are versus where your skill, experience and judgement currently stand(?)
If you have a local community of surfskiers usually there will be experience and judgement available before runs when big conditions appear. And often there will be honest and thorough discussions worth considering after runs in challenging conditions where problems have occurred or have been narrowly avoided.
Downwinding in a double is one way to get experience on bigger runs if you can team with a more experienced paddler. It is not uncommon for surfski instructors to introduce inexperienced paddlers to their first significant downwinding in a double surfski. Learning about bigger water in this manner can have some challenges, though. In sitting in the back of a surfski with the more experienced paddler steering in the front, one may get enough water in their seat to feel like they will imminently float off and out of the surfski. (Some doubles allow steering from either seat) The backseat paddler often gets a fairly steady shower of water in their face from the front seat paddle strokes. And even though the more experienced paddler may have the situation well in hand, it can feel to the less experienced paddler like their surfski is sometimes perilously off balance (though strong paddlers typically make double skis much more stable than inexperienced paddlers can make them on their own). On the other hand, if your experience of your first big downwinder seems completely trouble free because you have an expert paddler in your double with you, don't be fooled into thinking it should immediately be as simple and problem free for you in a single surfski. Bottom line - with a competent, experienced paddler in charge, a less experienced paddler can experience what an absolute blast downwinding can be in conditions that they are not yet capable of paddling solo.
from PonoBill on Standupzone.com: (talking about SUPs but this holds true for surfskis also)
“The primary reason swells roll under riders (paddlers) is that they (the swell) are moving too fast and have no definition or steepness on their face. The best riders accelerate their boards with small swells, hop to medium sized ones and then get the biggies. You really can't paddle fast enough to get the big on your own. If there isn't enough of that kind of texture (smaller and slower waves) you're not going to make it no matter how good you are…“