Well, I've only skippered a vessel once (my '74 Javelin), but I've already got a boneheaded move under my belt. It's a one-two punch.
1) I assumed that the previous owner had a clue when rigging the mainsheet. I was trying to sheet the main through one block on the centerboard trunk, shackled to the middle of the boom. 1:1 mainsheet purchase, even on a 14-foot boat, is no happy job. The fact that the cleat on the centerboard trunk was totally rounded off made things worse, as I had no way to keep her sheeted and rest my quickly-tiring hand/arm.
2) Since my arms and hands were getting tired, I decided to turn her up into the wind, sheet her in hard, and cleat it off (I can already hear you yelling at me
). I figured, "If I get a puff, I'll round up into the wind, and we'll do fine."
I made a couple of tacks, and we seemed to be doing well. It was about then I got the bright idea to give the jib a shot, so I hoisted it up, tacked, and sheeted it in too. I turned too far off the wind, and we got a puff, and no amount of rowing on the tiller was gonna point us back up. We started heeling madly, I stood on the trunk, leaning over the rail, and my girlfriend got drenched with entirely too much of the Cooper River, which was now flowing into the cockpit.
"Uncleat the main!" I yelled.
"What does that mean?", she yelled back.
"That! Take off that rope!"
She uncleated the mainsheet, I the jib, and we leveled off, sails flapping madly. I bailed for about 10 minutes with her water bottle, and we decided that was enough excitement for the day, we ran downwind, back to the boat ramp, and called it a night.
So, a little less luck, and a little more experience. Here's hoping the experience fills up before I run out of the luck