Once the decision is made to sail shorthanded, the main thing to concentrate on is the ease of handling of your boat. You will be assuming all the roles: skipper, dial trimmer, navigator, bow-person, engineer and chef. The ultimate goal is to make each of these positions as simple for yourself as possible. One of the best ways to figure out where to begin this process is to go out on your boat on a calm day and go through the motions of sailing the boat as if you were racing or cruising; hoisting sails, steering, trimming and navigating and see where you run into problems. Can you reef your mainsail by yourself? Is the spinnaker pole too much to handle on your own? Can you reach the sheeting positions from the helm?