When describing sailing to newbies, I generally tell them, "sailing is easy, sailing well is the hard part." What I mean is that assuming you have wind, sails, and a rudder, most people can get the boat to where they need to most of the time. It's not that hard to figure out.
What is hard is figuring out how to get the boat where you want when things go south. I've been following Francis Joyon's solo round-the-world-escapade pretty closely. Right about the time he was passing Cape Horn something or another went "bang" on his boat, the translated page said something along the lines of "he heard the noise and immediately knew what was wrong." That, my faithful reading public, is sailing well.
Pulling on the correct line at the right time helps your boat go faster and sail more efficiently and I think that's the first step to sailing well. But knowing exactly what's wrong when something goes bump in the night is the ultimate in sailing well. Because things break and things go bezerk. And you still have to get the boat where you want.
I'm no Joyon but I had a similar experience a few weeks ago that got me thinking about this subject. We were rounding the windward mark and were easing sail to head downwind. At this point, it's essential that the main trimmer and helm are acting in "cahoots". Well, we weren't. My main trimmer had released the sheet from the block and was staring at the main in confusion. See, the darn thing wasn't easing.
Thankfully, I'm getting to the point where I know my boat because to this day I'm not sure how I diagnosed the problem so quickly. I let go of the tiller, jumped onto the rail, pulled the bitter end of the outhaul line out of one of the mainsheet blocks, and was back at the helm before Mark even had a chance to start easing again. There were probably 10 different things that could have been wrong and somehow, in a gazelle-like imitation of Joyon, I had figured it out and rectified it without a single conscious thought.
I'm seriously proud of that moment (other than the letting go of the tiller part). I liken it to when I played tennis a lot, I didn't really feel my racket, it was like it was part of my arm. If I grabbed another racket, it felt cumbersome and unwieldy. I'm a LONG WAY from that level with Lady Bug but there are times when "sailing well" just comes naturally and it feels good.