Some years ago, I helped my best friend move from Detroit to Boston, and the following year, I moved her from Boston to Chicago. Needless to say, we worked out most of the kinks the second time around.
To make sure that your move is more fun than torture, preparation is key. Be sure to make a list of everything you need to move: boxes, enormous amounts of tape, and bubble wrap - do not pop them until you unpack; how much time you need to get to your destination - then add several days due to traffic, stopping to sightsee, or heck, just getting lost; and determine how much money the move will cost - then add another 25%. Keep in mind that there will always be surprises along the way, and make sure to take them in stride. Moving does not have to be a chore - it can be a road trip.

Some tips:
*LIGHTEN THE LOAD: Throw out or give away whatever you can manage prior to your move. The less you have to physically move, the easier the move. Seems logical, right? It’s not so easy.

*USE APPROPRIATE SIZE BOXES: The heavier the objects, the smaller the box, and vice versa. Be sure to label ALL your boxes (content and room), and on more than one side (it may get turned around in the moving van). Keep in mind that books are VERY HEAVY.

*RENT A VAN: Make sure you have an idea just how much you’re moving so you get the most appropriate size truck. Too large and you’re paying too much as well as risking the items shifting around. Too small and… well.. you have to unpack everything, get a new truck, and start over. NOT fun.

*GET A VAN WITH A/C AND A RADIO: This tip was borne of personal knowledge. Fortunately, we were lucky enough to get the proper size van. Unfortunately, we were stuck without a radio or A/C. Fortunately, we got along well enough to keep each other company for most of the night. Unfortunately, my friend doesn’t like to drive and likes to sleep. Fortunately, I can amuse myself… It’s all what you can handle.

*USE REST STOPS APPROPRIATELY: Don’t push yourself more than you can handle. Take frequent breaks, either to stretch your legs, to nap, or to grab snacks along the road. The human body can only handle so much monotony before it starts drifting.

*THINK OF TRAFFIC: My friend and I were driving from Boston to Chicago and there was a lot of construction between the two cities. Our solution? We didn’t leave Boston until after 5pm rush hour and drove throughout the night. That way, we missed all the traffic AND got to see a gorgeous sunrise.

*BRING A MAP: But don’t be afraid to ask for directions. Most people are incredibly helpful and polite. One lady in Boston even had us follow her in her car instead of trying to give us complex directions.

*REMEMBER IT’S AN ADVENTURE: Even if you’re leaving work, friends, or family behind, just remember that you are not just moving literally, you are moving figuratively. Better things may lie ahead, interesting people, and new experiences. Your friends and family will always love you, support you, and visit you. They only want the best for you.
One last thing. As my best friend and I always say, it’s not a road trip without at least one U-turn. The same can be said of life. Make the most of it!