Hi Hayden,
Having done a lot of water skiing, I felt like this wouldn't be too bad to try. As you can hear in the video, the plan was that if something went bad, Amanda would heave to. We heave to almost every time we sail, and usually the boat stops rather quickly. We were doing about 4 knots and that turned out to be much to fast. Fortunately, I had put the line on a winch!
As soon as I popped up, I yelled "Heave To" but of course Amanda could not hear me, she immediately dropped the camera and started grinding on the winch. It didn't take long to get to the side of the boat, however being on the windward side, with the boat heeling maybe 5 degrees, I could not reach the ladder, she had to winch me almost all the way up. I don't know how Redford did it in "All is Lost"! I believe if one was to go overboard , and in the water, with a safety lanyard attached, it would be near impossible to get back aboard. It was a huge learning experience! We are sailing to Catalina in a few days, preparing for the trip my plan is to install Jack lines. They as well as the safety lines will be rigged so that there should be no chance of going overboard.