I dang near tore the bow pulpit off a charter boat years ago, long before I owned my own boat. This was a 36 foot Dickerson that some friends and I got for a week of local use. I was about 30 at the time, and had a fair amount of sailing experience, but very little docking and none of that as skipper.
Mid-week of our charter, when everyone else was at work, I went down with my sort-of girlfriend (zero boating experience) to re-locate the boat for our next outing. We were alongside a pier to starboard, with a dock maybe twenty feet behind us. We were faced away from our destination, so I would have to turn the boat around. My plan was to just back away to port and get out into the channel, thinking that I had plenty of room to clear the dock behind us. But as soon as we started backing, the wind started the bow swinging much faster than expected. It became clear that it would swing into the dock that I had expected to clear, with quite a bit of force. My only choice was to gun the engine with just a few seconds to spare, and this allowed the bow to clear by a couple feet.
By luck, the wind continued to spin us around and quickly put us into position to motor down the channel. As we departed, some wiseacre called out, "Been a skipper long?!" I hollered back, "What are you, some crotchety old sailnetter?"