Docking as a means of self examination

How can a one activity fully wipe out my motivation by making me too anxious to pursue further activities? Close your eyes and picture; you are vessel of pure motivation riding a bitchin' surfboard to the island of happiness when a tsunami of fear tips you over short of landfall and the undertow of self-loathing drags you out to sea. Now picture the same, but with you holding the best hotdog in the world, one-with-everything, and as the wave crashes down, you now have a soggy bunned, sand covered dog with just a bit of onion to gaze on as the undertow drags you down. It can get worse, but I'll not commit the Haagen-Dazs scenario to written word.

Lets examine a case:

Docking. Sailing requires some type of docking maneuver, unless you buy the disposable type of boat I often see abandoned on the shoreline. I like sailing. I don't have anything against docking. Yet, unless I'm actually docking, I'm so paralyzed by the thought of having to dock, that I never allow myself to get to a place where docking is imminent, like out on the water on a boat. The fear of failure prevents my enjoyment, it doesn't just put a damper on it. Hence getting a sailboat, and almost never leaving the slip to go out.

My rational brain says I just need to dock all freaking day long until I get over the anxiety. What's the worst that can happen? I slam the boat into the pier and rather than sinking the boat, I sink the land, dropping all of North America under water, thus raising the sea level high enough to cause other continents to flood; single handedly causing the destruction of mankind before global warming even gets the chance. My real brain says, "Whoa, Nelly! That is fairly unlikely, but just in case... lets grab a book and a beer and enjoy the sun from dry land."

I'm working out some end runs to avoid facing my fears, and still getting around them permanently. For example, inviting other folks on the boat who can worry about docking, while I enjoy the water, and the beer they brought. Does that make me a coward, just a dork, or brilliant? Is it possible to achieve bliss by working around all those situations that anxiety blocks me from? Should I just start biting bullets? Why does he always end with a bunch of questions?