I don't deflate mine. I just strap it fully inflated on the back of my backpack. That way it is handy for floating across streams, lakes, and rivers. Plus, if I fall over backwards, I usually bounce right back up.
Just kidding. If possible, depending on the hammock, I pop the deflate valve while still on top in the hammock. Body weight deflates the pad. Then, or if the deflate valve isn't handy, I will do an initial deflate by wadding the pad into a ball in my lap as I'm standing, starting at the non-valve end. After the initial squeeze, I will unroll the pad and do a final roll. Sometimes the final roll is just another ball that I stuff in the bottom of the pack. And sometimes the final roll is the three part roll that the pad originally came as. The finial roll usually goes slow as I work out the last air reserve. The Synmats deflate much easier than the Downmats, but the Downmats are substantially warmer when needed. All is done without having to put the pad on the ground.
Oh, I almost forgot about the conspiracy. The pad makers have colluded together on making the original stuff sacks too small to reinsert the pad back into. This is done so that they can take pictures of the original packaging and proclaim, "See, our X pad is smaller than an aspirin bottle!". I rarely use the original stuff sack, except when putting the pad up on ebay for someone else to enjoy. Just too much hassle that I'm not willing to endure.
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