Rolling out the dough seems to be the part people fear the most. It really is not too bad if you follow a few simple rules.
Keep the table, dough, and rolling pin lightly dusted with flour. You don't want to use too much extra flour, but a light, even dusting is essential.
As you are rolling the dough, lift and turn it periodically to make sure it's not sticking, adding more flour and flipping the dough as needed.
It helps tremendously to use a guide of some sort to get your dough rolled evenly. You can use a rolling pin with built-in guide rings, or you can purchase rubber rings that will fit most regular rolling pins. A less expensive solution is to use 1/4" dowels placed on either side of your dough. Make sure your rolling pin is sitting on top of both dowels while rolling. It will do a great job at keeping your dough even.
Rolling Pin Rubber Rings
Quarter-inch wooden dowels
Smart Rolling Pin
Now that you have your beautiful, evenly rolled dough, you are finally ready to cut out your shapes! Make sure to cut your cookies as close together as possible. You want to cut your dough efficiently to limit the number of times you have to roll it out. First of all, it makes the dough tougher each time you roll it because of gluten development and the extra flour added each time. Secondly, it makes the process take longer if you have to roll it out too many times. Time is precious, and it's better spent decorating! My goal is to roll out the same ball of 3 times or less.